Justin Elliott

How a secretive billionaire handed his fortune to the architect of the right-wing takeover of the courts

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An elderly, ultra-secretive Chicago businessman has given the largest known donation to a political advocacy group in U.S. history — worth $1.6 billion — and the recipient is one of the prime architects of conservatives’ efforts to reshape the American judicial system, including the Supreme Court.

Through a series of opaque transactions over the past two years, Barre Seid, a 90-year-old manufacturing magnate, gave the massive sum to a nonprofit run by Leonard Leo, who co-chairs the conservative legal group the Federalist Society.

The donation was first reported by The New York Times on Monday. The Lever and ProPublica confirmed the information from documents received independently by the news organizations.

Our reporting sheds additional light on how the two men, one a judicial kingmaker and the other a mysterious but prolific donor to conservative causes, came together to create a political war chest that will likely supercharge efforts to further shift American politics to the right.

As President Donald Trump’s adviser on judicial nominations, Leo helped build the Supreme Court’s conservative supermajority, which recently eliminated Constitutional protections for abortion rights and has made a series of sweeping pro-business decisions. Leo, a conservative Catholic, has both helped select judges to nominate to the Supreme Court and directed multimillion dollar media campaigns to confirm them.

Leo derives immense political power through his ability to raise huge sums of money and distribute those funds throughout the conservative movement to influence elections, judicial appointments and policy battles. Yet the biggest funders of Leo’s operation have long been a mystery.

Seid, who led the surge protector and data-center equipment maker Tripp Lite for more than half a century, has been almost unknown outside a small circle of political and cultural recipients. The gift immediately vaults him into the ranks of major funders like the Koch brothers and George Soros.

In practical terms, there are few limitations on how Leo’s new group, the Marble Freedom Trust, can spend the enormous donation. The structure of the donation allowed Seid to avoid as much as $400 million in taxes. Thus, he maximized the amount of money at Leo’s disposal.

Now, Leo, 56, is positioned to finance his already sprawling network with one of the largest pools of political capital in American history. Seid has left his legacy to Leo.

“To my knowledge, it is entirely without precedent for a political operative to be given control of such an astonishing amount of money,” said Brendan Fischer, a campaign finance lawyer at the nonpartisan watchdog group Documented. “Leonard Leo is already incredibly powerful, and now he is going to have over a billion dollars at his disposal to continue upending our country’s institutions.”

In a statement to the Times, Leo said it was “high time for the conservative movement to be among the ranks of George Soros, Hansjörg Wyss, Arabella Advisors and other left-wing philanthropists, going toe-to-toe in the fight to defend our constitution and its ideals.” Leo and representatives for Seid did not immediately respond to requests for comment.

The Marble Freedom Trust is a so-called dark money group that is not required to publicly disclose its donors. It has wide latitude to spend directly on elections as well as on ideological projects such as funding issue-advocacy groups, think tanks, universities, religious institutions and organizing efforts.

The creators of the Marble Freedom Trust shrouded their project in secrecy for more than two years.

The group’s name does not appear in any public database of business, tax or securities records. The Marble Freedom Trust is organized for legal purposes as a trust, rather than as a corporation. That means it did not have to publicly disclose basic details like its name, directors and address.

The trust was formed in Utah. Its address is a house in North Salt Lake owned by Tyler Green, a lawyer who clerked for Supreme Court Justice Clarence Thomas. Green is listed in the trust’s tax return as an administrative trustee. The donation does not appear to violate any laws.

Seid’s $1.6 billion donation is a landmark in the era of deregulated political spending ushered in by the Supreme Court’s 2010 Citizens United decision. That case, along with subsequent changes and weak federal oversight, empowered a tiny group of the super rich in both parties to fund groups that can spend unlimited sums to support candidates and political causes. In the last decade, donations in the millions and sometimes tens of millions of dollars have become common.

Individuals could give unlimited amounts of money to nonprofit groups prior to Citizens United, but the decision allowed those nonprofits to more directly influence elections. A handful of billionaires such as the Koch family and Soros have spent billions to achieve epochal political influence by bankrolling networks of nonprofits.

Even in this money-drenched world, Seid’s $1.6 billion gift exceeds all publicly known one-time donations to a politically oriented group.

The Silent Donor

One day in November 2015, the employees of Tripp Lite, a manufacturer of power strips and other electrical equipment, gathered for a celebration at the company’s headquarters on the South Side of Chicago. Cupcakes frosted in blue and white spelled out the numbers “56.” An easel held up a sign hailing Tripp Lite’s longtime leader: “Congratulations Barre!”

A small, balding man with a white goatee and a ruddy complexion took the microphone. Barre Seid was known as someone who preferred to keep a low profile, but on the 56th anniversary of his leadership of Tripp Lite, he couldn’t resist the chance to address his employees. Later, as he bit into a cupcake, Seid posed for a company photographer, who later uploaded the photo to the company’s Facebook page.

Even this semipublic glimpse of Seid was rare.

For several decades, a select group of political activists, academics and fundraisers was ushered to Tripp Lite headquarters to pitch Seid at his office. Despite his status as one of the country’s most prolific funders of conservative causes, and despite his decades as the president and sole owner of one of the country’s most successful electronics makers, Seid has spent most of his 90 years painstakingly guarding his privacy.

There are no art galleries, opera companies, or theaters or university buildings emblazoned with his name in his hometown of Chicago. There’s even some confusion over how to pronounce his last name. (People who’ve dealt with him say it’s “side.”)

The Lever and ProPublica pieced together the details of his life and his motivations for his extensive donations through interviews, court records and other documents obtained through public-records requests.

One of the only photos of Seid that The Lever and ProPublica could find shows him as a 14-year-old walking in a small group across a college campus. Born in 1932 to Russian Jewish immigrants, Seid grew up on the South Side of Chicago, the oldest of two brothers, according to Census records. A precocious child, he was chosen for a special bachelor’s degree program at the University of Chicago, not far from his childhood home.

Seid attended the University of Chicago in the early years of the “Chicago school,” a group of professors and researchers who would reimagine the field of economics, assailing massive government interventions in the economy and emphasizing the importance of human liberty and free markets. After college, Seid served two years in the Army and eventually returned home to Chicago, according to testimony given decades later in a court case. He took a job as an assistant to an investor and businessman named Graham Trippe, whose company made headlights and would produce the rotating warning lights used by police cars, tow trucks and other emergency response vehicles.

By the mid-1960s, Seid had taken over as Trippe Manufacturing’s president. In the decades to come, the company, now called Tripp Lite, became a pick-and-shovel business of the digital gold rush. The company sells the power strips that supply electricity to computers and the server racks, cooling equipment and network switches that make data centers run. Business surged with the shift to cloud computing and the proliferation of vast data centers.

That boom vaulted him from the ranks of merely rich to the superrich. Seid was making around $30 million per year by the mid-1990s, tax records obtained by ProPublica show. His annual income, the vast majority of which came from Tripp Lite’s profits, took off in the mid-2000s and steadily rose, hitting around $157 million in 2018. Tripp Lite, which was 100% owned by Seid, contributed $136 million to his total income that year.

Even as Seid built a billion-plus dollar business, he drew scant public attention; Forbes never put him on its list of the wealthiest Americans, and business and political press rarely mentioned him.

Yet he was becoming a major donor. He gave at least $775 million in charitable donations between 1996 and 2018, a period in which he reported $1.7 billion in income, according to his tax records. Seid parceled out a small portion of those donations to Chicago-area universities, religious organizations, medical research and dozens of civic-focused groups.

While Seid has never spoken to the press about his ideology, evidence of his worldview has emerged here and there. His family foundation has supported the University of Chicago’s Becker Friedman Institute for Economics, named after two of the Chicago school’s intellectual leaders, Gary Becker and Milton Friedman. He has also donated to the Heartland Institute, a Chicago-based nonprofit that has a history of using inflammatory rhetoric and misleading tactics to undermine climate science.

Seid appeared to be the donor (listed as “Barry Seid”) who gave $17 million to fund the distribution during the 2008 presidential campaign of millions of copies of a DVD of the film “Obsession: Radical Islam’s War With the West.” The DVDs, which were sent specifically to households in presidential election battleground states, were criticized as virulently anti-Muslim.

Seid’s personality can be glimpsed in exchanges with George Mason University officials from the late 2000s to mid-2010s that came out in response to a public-records request by the activist group UnKoch My Campus. In the emails, Seid comes across as an intellectually probing figure, asking the dean of the law school to respond to news stories about the value of a law-school degree or the workings of higher education’s accreditation system. Seid drily addressed several administrators for the university, whose law school and economics department are known for their alignment with conservative, free-market principles, as “Fellow Members of the Vast Right Wing Conspiracy.”

Seid appears to have continually sought new vehicles for dispensing his money and maintaining as much anonymity as possible. The GMU emails also show a redacted donor — who activists believed to be Seid based on other unredacted materials — routing donations to the school through DonorsTrust or the Donors Capital Fund, two donor-advised funds that provide an additional level of anonymity.

While the roots of Seid and Leo’s professional relationship aren’t clear, the two worked together at a small foundation Seid formed in 2009 called the Chicago Freedom Trust, a charity that gave out small grants to nonpolitical groups. Leo later joined the foundation’s board.

The GMU emails provide an inkling of the relationship between the two men. In early 2016, Seid emailed the dean of GMU’s law school and the head of a prominent American Jewish organization to urge them to work together. The dean, Henry Butler, forwarded Seid’s message to Leo seeking to better understand Seid’s intentions.

“Do you have any insight?” Butler wrote.

“I do not, but will find out,” Leo replied.

The Money

Billionaires tend to craft intricate estate plans to pass the family business to the next generation, fortified from taxation and protective of their vision. The apparently childless Seid didn’t have that option, but starting in April 2020, he set in motion a plan to make sure his fortune would go toward his favored causes.

That month, the Marble Freedom Trust was created, and Seid subsequently transferred his 100% ownership stake in Tripp Lite to the trust, according to the documents reviewed by The Lever and ProPublica.

In February 2021, Tripp Lite filed its annualreports with the state of Illinois as it had done for decades. But this time, Seid’s typewritten name had been crossed out as an officer of the company. Added as an officer, written in by hand, was Leonard Leo.

A Tripp Lite subsidiary in Nova Scotia, Canada, similarly removed Seid as a director and added Leo as a director in March 2021, according to disclosure filings.

Then, later that same month, Eaton Corporation, a large publicly traded company, acquired Tripp Lite for $1.65 billion.

The transactions appear to have been carefully sequenced to reap massive tax savings. Selling a company that has grown in value after decades of ownership is treated the same way for tax purposes as a person selling a share of stock. If the property has grown in value, capital gains taxes are due when it is sold.

But Seid transferred Tripp Lite to the Marble Freedom Trust, a nonprofit that is exempt from income tax, before the electronics company was sold. As a result, lawyers say, Seid avoided up to $400 million in state and federal income tax, preserving those funds for Leo’s operation.

“If the person who had owned the stock had sold the stock himself, he would’ve been taxed on the appreciation in the stock,” said Ellen Aprill, a tax law professor at Loyola Marymount University. “Whereas if you give it to the 501(c)(4), there’s no charitable deduction for giving the money, but you avoid the tax on all of that appreciation.”

Political advocacy nonprofits like the Marble Freedom Trust are formally called 501(c)(4) social welfare organizations, after the section of the tax code. Informally, they are known as dark-money groups because donors can remain secret, in contrast to the public disclosures required of gifts to political campaigns or super PACs. While they can spend money directly advocating for or against candidates in political campaigns, such spending cannot be their primary purpose.

In giving to such a dark money group, Seid also avoided another federal levy, the gift tax, thanks to a change signed into law by President Barack Obama in 2015.

There’s a reason why giving money specifically to a trust might have been attractive for an older and ideological donor such as Seid. The founding documents that lay out how the trust will spend money can be harder to change than the governing documents of a corporation, according to Lloyd Hitoshi Mayer, a professor at Notre Dame Law School.

Mayer added that while corporations usually have at least three directors, trusts can have just a single trustee in charge of the organization’s activities.

Leo is the trustee and chairman of the Marble Freedom Trust. In other words, Leo is now in charge of the massive sum of money.

The Rainmaker

For decades, Leo had served as a top executive at the Federalist Society, helping lead the influential Washington-based conservative lawyers group that serves as a launching pad for careers on the right.

But in early 2020, Leo made an announcement that suggested he was taking his successful model for reshaping the courts to remake American politics at every level: local, state and federal. In an interview with Axios, Leo said he was stepping away from his day-to-day role with the Federalist Society to take a more active role steering a network of conservative dark money groups.

The plan was to expand the network’s scope to “funnel tens of millions of dollars into conservative fights around the country,” according to Axios. What Leo did not mention in the interview was the imminent creation of the Marble Freedom Trust, his biggest-ever war chest.

Leo’s long career as both a legal activist and a prodigious fundraiser for conservative causes shows a steady march toward becoming a central figure in the Republican Party’s successful strategy to fill as many judicial vacancies as possible with young, conservative judges skeptical of the federal government’s power. He served as an adviser to Trump’s 2016 campaign, helping the candidate take a step no other major presidential candidate had ever taken: releasing a list of names he would draw on to nominate to the Supreme Court.

Coming at a moment when conservatives were wary of Trump’s past leanings, the move bolstered his support among social conservatives. Leo stayed on as a judicial adviser during Trump’s four years in office. During that time, Leo helped the president appoint and confirm more than 200 nominees to the federal bench, most famously Supreme Court Justices Neil Gorsuch, Brett Kavanaugh and Amy Coney Barrett.

Leo’s efforts to reshape the country’s judicial system began long before Trump’s political ascent. In 1991, he joined the Federalist Society, which was then in its early years and only beginning to build a pipeline for conservative jurists.

In the view of Leo and his allies, the U.S. legal system had drifted dangerously far from its roots, establishing privileged classes and doctrines that were not enumerated in the Constitution and would be unrecognizable to the Founders. Those same courts had also empowered a class of unelected bureaucrats dubbed the “administrative state” to impose needless regulations and to endow the federal government with too much power. Like his close friend Justice Antonin Scalia, Leo argued for an originalist view of the Constitution — namely, that the country’s founding document should be interpreted strictly based on how its 18th century authors understood its words at the time.

In 2005, Leo and his allies formed a dark money network to rally support for George W. Bush’s Supreme Court nominees, John Roberts and Samuel Alito. But if Leo wanted to turn back the tide of what he saw as unchecked judicial activism, he needed to build something bigger, more lasting.

Leo set out to create a network of interlocking groups that could each play a part in returning the country to what he saw as its roots, whether by training future generations of Scalias, funding scholarship that made the case for originalism or bankrolling efforts to install conservative judges on the bench.

Between 2005 and mid-2021, Leo and his associates raised at least $460 million (not including the Marble Freedom Trust’s funds).

According to tax records, Leo’s network has funneled those hundreds of millions into ad campaigns and right-leaning groups. The Judicial Crisis Network — which is now called the Concord Fund and is headed by a former clerk to Justice Clarence Thomas and Leo associate named Carrie Severino — has spent tens of millions airing ads during Supreme Court confirmation fights.

The group’s fundraising took off in 2016, when it led a campaign to block Obama Supreme Court nominee Merrick Garland’s confirmation. That year, Leo’s network received a $28 million infusion from a single anonymous donor. Leo and his network long refused to say who is paying for their advocacy campaigns.

Leo’s network has worked closely with Senate Republicans and has showered them with cash as well, recently donating $9 million to a dark money group affiliated with Senate Minority Leader Mitch McConnell, R-Ky.

While Leo is best known for his influence on the Supreme Court, he and his network have also worked to shift the balance of power throughout the judiciary — in federal district and appellate courts, and state supreme courts, too.

At the state level, the network funds groups supporting conservative gubernatorial and legislative candidates. Leo’s nonprofits and their subsidiaries have recently pushed states to tighten voting laws, opposed the teaching of critical race theory in schools and financed organizations pressing states to remove millions of Americans from the Medicaid rolls.

But now, with Seid’s largesse, Leo has nearly four times the amount he raised over 16 years at his disposal and ambitions to match.

“I have a very simple rule, which is, I’m engaged in the battle of ideas, and I care very deeply about our Constitution and the role of courts in our society,” Leo told The Washington Post in 2019 when asked about his donors. “And I don’t waste my time on stories that involve money and politics because what I care about is ideas.”

Meet the billionaire and rising GOP mega-donor who’s gaming the tax system

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Series: The Secret IRS Files

Inside the Tax Records of the .001%

One day in July 1985, three young men from Philadelphia, their lawyer and a burly Pinkerton guard arrived at a horse track outside Chicago carrying a briefcase with $250,000 in cash.

Running the numbers on a Compaq computer the size of a small refrigerator, Jeffrey Yass and his friends had found a way to outwit the track’s bookies, according to interviews, records and news accounts. A few months earlier, they’d wagered $160,000, gambling that, with tens of thousands of bets, they could nail the exact order of seven horses in three different races. It was a sophisticated theory of the racing odds, honed with help from a Ph.D. statistician who’d worked for NASA on the moon landing, and it proved right. They bagged $760,000, then the richest payoff in American racing history.

But that summer day, when they presented their strikingly long list of bets at the track window, they were turned away. Their appeal to the track owner got them ejected. Yass, just 27, then sued for the right to place the bets. The track’s lawyer fumed to a federal judge that the men were trying to corner the betting market “through the use of their statistics and numbers.”

Yass lost, but that year he and his friends repeated variations of the strategy at horse and greyhound tracks around the country. Then they decided to turn their focus from a world of hundreds of thousands of dollars to a world of billions: Wall Street.

Four decades later, the firm he and his friends founded, Susquehanna International Group, is a sprawling global company that makes billions of dollars. Yass and his team used their numerical expertise to make rapid-fire computer-driven trades in options and other securities, eventually becoming a giant middleman in the markets for stocks and other securities. If you have bought stock or options on an app like Robinhood or E-Trade, there’s a good chance you traded with Susquehanna without knowing it. Today, Yass, 63, is one of the richest and most powerful financiers in the country.

But one crucial aspect of his ascent to stratospheric wealth has transpired out of public view. Using the same prowess that he’s applied to race tracks and options markets, Yass has taken aim at another target: his tax bill.

There, too, the winnings have been immense: at least $1 billion in tax savings over six recent years, according to ProPublica’s analysis of a trove of IRS data. During that time, Yass paid an average federal income tax rate of just 19%, far below that of comparable Wall Street traders.

Yass has devised trading strategies that reduce his tax burden but push legal boundaries. He has repeatedly drawn IRS audits, yet has continued to test the limits. Susquehanna has often gone to court to fight the government, with one multiyear audit battle ending in a costly defeat. The firm has maintained in court filings that it complied with the law.

Yass’ low rate is particularly notable because Susquehanna, by its own description, specializes in short-term trading. Money made from such rapid trades is typically taxed at rates around 40%.

In recent years, however, Yass’ annual income has, with uncanny consistency, been made up almost entirely of income taxed at the roughly 20% rate reserved for longer-term investments.

Congress long ago tried to stamp out widely used techniques that seek to transform profits taxed at the high rate into profits taxed at the low rate. But Yass and his colleagues have managed to avoid higher taxes anyway.

The tax savings have contributed to an explosion in wealth for Yass, who has increasingly poured that fortune into candidates and causes on the political right. He has spent more than $100 million on election campaigns in recent years. The money has gone to everything from anti-tax advocacy and charter schools to campaigns against so-called critical race theory and for candidates who falsely say the 2020 election was stolen and seek to ban abortion.

ProPublica has pieced together the details of Yass’ tax avoidance using tax returns, securities filings and court records, as well as by talking to former traders and executives. (The former employees spoke on condition of anonymity, with many citing a desire to avoid angering Yass.)

Through a spokesperson, Yass declined to be interviewed for this article. The spokesperson declined to comment in response to a long list of questions for Susquehanna and the firm’s founding partners.

Gregg Polsky, a University of Georgia law professor and former corporate tax lawyer who was retained by ProPublica to review Susquehanna’s tax records, said the tax agency may have more to scrutinize. The strategies revealed in Yass’ records, he said, were “very suspicious and suggestive of potential abuse that should be examined by the IRS.”

More than 35 years after he was booted from the racetrack outside Chicago, Yass still lives to gamble. Not just on horses, but on poker and on the market. He sheepishly admitted, in a podcast discussion, that he has even placed wagers on his children’s sports games.

Asked to describe his approach to trading at Susquehanna, Yass once reached for a poker analogy. “If you’re the sixth-best poker player in the world and you play with the five best players, you’re going to lose,” he said. “If your skills are only average, but you play against weak opponents, you’re going to win.”

That philosophy along with, Yass freely admits, a lot of luck, has made him a billionaire many times over.

Compared to many of his fellow billionaires — he’s richer than Hollywood mogul David Geffen, retail brokerage king Charles Schwab and “Star Wars” creator George Lucas — Yass doesn't seem particularly interested in the trappings of extreme wealth.

Yass and his wife, Janine, raised four children in the leafy college town of Haverford, on the Main Line outside of Philadelphia. Their large but unremarkable house could easily be the home of a successful doctor rather than one of the richest men in the country. In his quarter-zip pullover sweater, Nikes and no-nonsense rimless glasses, he’d be impossible to pick out of a crowd at the suburban country club where he plays golf.

If Yass collects expensive art or maintains a megayacht, he has managed to do so in complete secrecy. What comes closest to an identifiable trophy asset is a house in the ultra-exclusive Georgica Association beach neighborhood of East Hampton on New York’s Long Island. Even that property, purchased for $12.5 million in 2005 and held through an LLC, is in an area known as “bucolic and understated.”

Those who have worked with Yass say he lives less for spending money than for the competition of the market and the thrill of taking calculated risk. Yass softens any impression of ruthlessness by deploying a practiced humility and comedic timing. “Some people like art history,” he once explained, “I like probabilistic analysis.”

Yet when it comes to his philosophical outlook, he eschews the jokes. He speaks of capitalism in religious terms. Making new markets, he likes to say, is a “mission from God.”

Like many religious stories, his begins with a conversion experience. Born in 1958 to two Queens CPAs, Yass said reading the economist Milton Friedman’s “Capitalism and Freedom” as a young man delivered him from an early flirtation with socialism.

By the time Yass graduated from the State University of New York at Binghamton in 1979, he was already captivated by trading. (His father had also helped nurture Yass’ love of horse racing by taking him to local tracks to see harness racing, according to Forbes.) Yass’ college thesis weighed whether the budding market in stock options could be justified as socially useful. “I concluded that it should exist,” Yass later cracked. “I got a B.”

After college, he moved to Las Vegas for a year and a half to play poker professionally. Then he returned to the East Coast and settled in Philadelphia, where he began trading options. The previous decade had seen a burst of academic interest in the financial instruments, including a pioneering model of how to more accurately price them. Yass later called the model, and its broader implications for how to make mathematically sound decisions, “the most revolutionary idea in a long, long time.”

A share of stock is a relatively simple concept: It’s a small ownership stake in a company. An option, by contrast, is a contract that confers the right to buy or sell a given stock at a particular price and time in the future.

Options attract mathematically minded traders since a complex set of variables, including the underlying stock price, volatility, time and interest rates, determine how much one of the contracts is worth.

Options are a versatile tool. They can appeal to the risk-averse: Traders can use them as insurance to guarantee they will be paid at least today’s price when they sell in the future. They are also useful to the risk-embracing — gamblers who want to place outsized bets on how a stock will perform. (Here’s how a speculator would use an option: In early June, shares of Netflix were trading at below $200. If the speculator thinks the company’s fortunes will improve dramatically this summer, they could pay just $4.50 each for options to buy the stock at $250 in mid-August. If the stock soars over that figure, they could make a mint.)

In options Yass found more than a financial instrument. He found a way to view the world. Everything — each decision, each interaction — can be judged based on how much it will cost in money, time or negative consequences and compared with the reward. Then action is taken or avoided accordingly. To Yass’ way of thinking, it’s always worth paying $19 for a 20% chance to win $100 but it’s never worth $21.

Along with his college friends, Yass founded Susquehanna, named after the river that connects Binghamton to Pennsylvania, in 1987. The firm benefited from explosive growth in options markets. Yass later played it down to the Philadelphia Inquirer: “We got lucky being in the right place at the right time.”

One of Susquehanna’s landmark moments — involving perhaps both skill and luck — occurred soon after the firm launched: the Black Monday stock market crash on Oct. 19, 1987. Thanks to an option bet that would pay out if stocks went down, Susquehanna was one of the few firms that made money on one of the worst days in stock market history.

From early on, Yass cultivated Susquehanna’s brand as a home for the biggest brains in finance, hiring Ph.D.s and top students. But the firm wasn’t just looking for raw IQ points. It also wanted instinct. It held poker tournaments to teach traders the idea that taking the measure of your opponents is as important as understanding the odds.

The Binghamton buddies ran a freewheeling office full of arguments and gamesmanship. The office had Super Bowl pools and an officewide lottery. Everyone bet on everything. One time, as recounted in Philadelphia magazine, traders bet on whether Yass could name the last Plantagenet king of England. They called Yass. He spat out “Richard III” and then, according to a witness, yelled, “Get back to work!” But he liked the hijinks.

Still, the firm had an inside vs. outside mentality. If you weren’t with the firm, you were the enemy. When traders left to join a competitor, Susquehanna often sued them for allegedly violating non-compete clauses. Susquehanna stood out for its aggressiveness in trading even by the standards of Wall Street. “If he thinks you’re dumb, he’s betting against you,” one former Susquehanna trader said of Yass. “That’s what makes his blood flow.”

Susquehanna developed a specialty in arbitrage, or finding low-risk profit opportunities in mismatched prices of securities, like stocks or bonds. An early adopter of computers to measure risk and test trading strategies, the firm flourished.

In addition to making his own bets, Yass built his firm into one that stands at the very center of the market and takes bets from other traders. On Wall Street, this job is known as market making.

At its simplest, making a market means offering to buy or sell a thing. The jewelry shop on the corner that will sell you a gold ring and has a “We Buy Gold” sign in the window is making a market in gold. If the store buys a gold coin from a customer for $300, then sells it for $320 to the next person who walks in, the store has made a quick $20.

Susquehanna does the same thing, but with securities. Running a market making firm isn’t always as easy as quickly matching a buyer and a seller. A market maker is expected to post its prices and buy and sell to all comers. If a particular stock has more sellers than buyers, the firm might find itself holding too much, exposing the market maker to losses if the stock price drops. It’s a business that thrives when there’s lots of trading volume but can be dangerous if markets crash.

The market making business in stock options, Susquehanna’s specialty, requires juggling a huge number of trades while constantly keeping an eye on all the various bets to make sure that the firm is protected from unexpected market moves.

In 1996, the year Yass turned 38, he made $71 million, tax records show. By then, the firm was employing hundreds of people. Not long before, Susquehanna staff had gathered in Las Vegas for an annual company celebration. Traders brought their families. The firm’s employees watched the Kentucky Derby together. A Marilyn Monroe impersonator interviewed Yass’ father with some tame double-entendres. The highlight was a skit with a junior trader performing as “Jeff Yass Gump,” after Forrest Gump. “Momma always said I was like the other kids,” the trader said. “But the other kids, they went to Harvard and Yale and the University of Pennsylvania and I said: ‘Momma, why am I at the SUNY Binghamton?’ She said it was because I was special.” The crowd roared, Yass the loudest of all.

Despite losing some star traders in the late 1990s, Susquehanna continued to produce massive profits. Yass and the other co-founders managed to keep their enormous wealth a secret. Even by 2005, when Yass had collected at least $1 billion of lifetime income, he was nowhere to be found in the Forbes list of the richest Americans.

That’s in part because Susquehanna is privately held and trades only its own money, meaning it doesn’t have to publicly disclose much about its business. Like many financial firms, Susquehanna itself is not a single company but a complex and shifting web of legal entities whose profits flow to Yass and a small set of partners.

It has been a remarkably consistent profit machine for the partners, except in 2008, the year of the global financial crisis. Yass alone lost $470 million that year, tax records show. Former Susquehanna traders believe the firm risked going out of business. The danger the firm faced “sent chills through everyone,” said one. Like other big trading complexes that did huge business with investment banks, Susquehanna benefited from the massive federal bailout of Wall Street, which propped up the giant firms that were among its biggest trading partners.

Yass, the free market true believer, now owed the survival of much of his fortune to the U.S. government. On a personal level, Yass also received an extra bonus from the government: a $2,000 child tax credit because he reported losing money that year.

Susquehanna quickly bounced back to profitability. In recent years it has supplanted major banks as one of the firms that sits in the middle of massive daily financial flows in stock and other markets. A Bloomberg profile in 2018 reported that Susquehanna trades 100 million exchange-traded fund shares daily. The firm is a prominent player in cryptocurrencies like bitcoin and, in a throwback to Yass’ origins, the exploding business of sports betting. Susquehanna has also branched out into venture capital. One of those investments came through spectacularly: a large stake in ByteDance, the Chinese company behind the social media app TikTok.

By the 2010s, Yass had become one of the richest Americans. But his ultralow profile meant that almost nobody knew that. At least two of Susquehanna’s other co-founders, Arthur Dantchik and Joel Greenberg, have each made billions of dollars themselves, according to ProPublica's analysis.

Yass hit a new milestone in 2012, pulling in more than $1 billion in a single year, according to tax records; by 2018, his income was $2 billion. In the six years ending in 2018, Yass had the sixth-highest average income in the entire country, according to IRS data.

Court filings and ProPublica’s analysis of tax records suggest that, as of 2018, Yass owned around 75% of Susquehanna, with co-founders Dantchik owning around 19% and Greenberg around 3%. (Greenberg retired in 2016.)

Yass was finally added to the Forbes list last year. The magazine put his worth at $12 billion, which would make him the 58th-richest American. ProPublica estimates his true wealth is likely at least $30 billion — based solely on his income over the decades and stake in ByteDance — which would place him in the top 25.

On a Friday afternoon in April 2010, a Susquehanna trader in Pennsylvania emailed his counterparts at Credit Suisse to make a big bet in the stock market. The email instructed the Swiss bank to buy about $70 million worth of shares in some of Switzerland’s biggest companies on Susquehanna’s behalf.

Three minutes later, the trader sent out a second email, this time to Morgan Stanley. He placed a second bet, now wagering against the exact same stocks in the exact same amounts he’d just ordered from Credit Suisse.

The payoff from such a trade might seem to be nothing at all. But there was a winner and a loser. The winner was Susquehanna. The loser was the U.S. government: Susquehanna had managed to slash its tax bill through the trade. The emails come from an ongoing U.S. Tax Court case filed in 2020. There are rules designed to block clever traders from using offsetting bets to conjure tax savings, and the IRS argues Susquehanna broke them. (More on that case later.)

The firm’s willingness to push the boundaries of tax law is not surprising to people who know Yass and his partners. One former Susquehanna executive recalled Yass acknowledging using a trading strategy in which a main goal was not to make profitable trades, but to avoid taxes. Taxes, according to Yass’ former colleagues, are an obsession for the billionaire. As one former employee put it, “They hate fucking taxes.”

It doesn’t matter how seemingly trivial it is. Susquehanna once petitioned the state of Pennsylvania to demand “a refund of taxes paid on repairs to ice machines.” The petition was denied.

Indeed, the firm has a habit of shaping deals that slash its tax bill and then daring the IRS to intercede. Sometimes, the agency successfully challenges them, as when Yass and his two main partners were hit with a total of $121 million in back taxes in 2019. That was the single biggest such payout in ProPublica’s database of IRS records, which includes thousands of audits of the wealthiest people in the country. Susquehanna paid only after losing a long-running battle with the agency, one the firm appealed all the way to the Supreme Court.

Despite periodically tripping IRS wires, the firm’s aggressiveness seems to have paid off. Susquehanna’s tax avoidance has gone on for years, resulting in a strikingly low tax rate for Yass and his partners, according to ProPublica’s analysis.

The strategy behind that trade back in 2010 is key to understanding how they’ve done it. Similarly to how Susquehanna has taken advantage of small differences in prices of options or stocks, it has found ways to exploit a gap in tax rates to save hundreds of millions of dollars in taxes every year.

For someone like Yass, the U.S. system offers an almost irresistible proposition. If you earn the wrong sort of income — the kind that comes from a short-term trade — you’ll pay a relatively high tax rate. But if you earn the right kind — gains on long-held investments — you’ll pay half as much in taxes.

But what is considered “long-term” involves a bright, arbitrary line. Hold a security for less than 366 days, and you are on the wrong side of that line.

The result is that by the arithmetic of the U.S. tax code, $100 made from a sale on the 365th day is worth around $60 after taxes. And $100 made on the 366th is worth around $80.

Short-term, high-frequency traders like Susquehanna often hold securities for less than 365 seconds. As the company itself put it in one recent court filing, the firm “trades securities, commodities, and derivatives, seeking to earn returns from short-term appreciation and arbitrage profits.” This has been the firm’s consistent self-description. Back in 2004, a staffer was more frank in testimony: “We are not, by our nature, into holding stocks.”

With such an approach, long-term gains should be forever out of reach.

And yet, Yass and his partners have managed, year after year, to report that the vast majority of their net income came in the form of long-term capital gains. In several recent years, 100% of their income was taxed at the lower rate.

How do they do it?

One strategy, in simplified form, works like this: Make two bets that should move in opposite directions. Think of, say, both betting on and against Coca-Cola’s stock. Towards the end of the year, one bet will be up, and one will be down. At 365 days, the last day a trade is considered short-term, sell the one that’s down. A day later, sell the one that’s up.

Of course, if you consider the trade as a whole, it makes no money. But that isn’t the point. You’ve found a risk-free way to generate two valuable commodities: short-term losses and long-term gains.

On their own, these losses and gains aren’t of much use. But to someone like Yass, who separately generates an enormous pile of short-term gains each year, they work a kind of magic.

That’s because of how taxes are calculated. Short-term and long-term results are accounted for in separate buckets: Short-term losses are applied first to short-term gains. So the losses from the Coke trade reduce the existing pile of short-term gains. The money made from the Coke trade, meanwhile, goes in the long-term bucket.

In the end, the trader has essentially transformed short-term gains into long-term gains, the type taxed at the special lower rate. From 2003 through 2018, the difference between the two rates ranged from 17 to 20 percentage points. So, for every $100 run through this process, the trader would net from $17 to $20 in tax savings.

So why isn’t everyone using this strategy?

Because as laid out here, it would be illegal.

For decades, traders have devised strategies that looked something like the Coke trade, known as a “straddle” because the trader is taking both sides. Over the years, Congress passed laws and the IRS imposed intricate rules to stop them, taking away the tax benefit of simultaneously betting for and against the same stock.

And yet, Yass and his partners built a machine that produced much the same result.

Since 2011, IRS records show, a partnership called Susquehanna Fundamental Investments has been the source of the majority of long-term gains for Yass and his partners. Every year, it channeled hundreds of millions in long-term gains to them, while also providing hundreds of millions in short-term losses.

Year after year, the gains and losses rose and fell roughly in tandem, as if one were a near reflection of the other. In 2015, for example, Susquehanna Fundamental produced $774 million in long-term gains and $787 million in short-term losses for Yass. In 2017 it was $940 million in long-term gains and $902 million in short-term losses.

Regulatory filings give a glimpse of the fund’s trading.

Susquehanna Fundamental has to disclose a snapshot of certain holdings with the Securities and Exchange Commission a few times each year, though many types of trades are exempt from disclosure.

Over several years, the fund’s disclosed positions resembled a complex version of the Coke trade. Instead of betting for and against a single stock, the firm bet for and against the entire market.

Susquehanna Fundamental held billions of dollars of individual stocks such as Google, Wells Fargo and, as it happens, Coca-Cola. These stocks were among the largest companies in the S&P 500 index.

Meanwhile, the fund also held a large bet against the S&P 500. In essence, it held a bet against many of those exact same stocks.

On its face, the fund actually lost money for Yass: Over eight years, it registered $5.4 billion in losses against $5 billion in gains — a net loss before taxes. But by transforming the tax rate on so much income, it delivered $1.1 billion in tax savings, and Yass came out way ahead.

It’s not clear whether the IRS has ever challenged the firm’s trading inside Susquehanna Fundamental Investments.

But the trading pattern has similarities to the 2010 Swiss stock trades, which involved betting for and against the exact same stocks. The IRS deems those to have been illegal under tax law.

Those trades were part of a larger deal worked out by Susquehanna and Morgan Stanley that called for the Philadelphia firm to buy $1.4 billion of the stocks and simultaneously bet against them, court records show. (Morgan Stanley declined to comment.) Over the next three years, the deal kicked out at least $365 million in low-rate income to the firm, while generating massive losses that could be used to wipe out other high-rate income, according to the IRS.

When IRS auditors scrutinized the deal, they found that Susquehanna had violated rules against betting for and against the exact same stocks. The agency demanded the firm pay tens of millions of dollars in back taxes.

Yass and his partners refused, arguing that the firm had broken no rules, and sued the IRS in U.S. Tax Court in 2020. They asserted that the deal was supposed to be profitable and wasn’t primarily intended to avoid taxes. But the firm also acknowledged the deal was tailored with an eye to “tax efficiency.” The case is still pending, with Susquehanna currently resisting requests to turn over more documents.

Susquehanna’s ability to manufacture the right kind of income has helped Yass and his partners minimize their taxes for decades. Since 2001, Yass hasn’t paid over 20% in a single year. In 2005, a year when he made what was for him the modest sum of $66 million, he paid $0 in federal income tax.

For Yass’ primary competitors, the story is far different. Citadel and Two Sigma are both huge firms that, like Susquehanna, do a mix of lightning-fast trading and market making. The heads of these firms, like Yass, reported incomes larger than almost anyone else in the country from 2013 to 2018.

But the tax returns of these Wall Street titans — Ken Griffin from Citadel, and John Overdeck and David Siegel from Two Sigma — have no mystifying source of low-rate income.

They also differ from Susquehanna in another telling respect. These firms voluntarily classify their trading activity as ordinary income, according to ProPublica’s analysis of tax records. Doing this makes sense for a firm that specializes in short-term trading and doesn’t expect to generate many long-term gains. That’s why many high-frequency firms make this “Section 475 election,” as it’s called in the tax jargon. If Susquehanna elected to treat its trading this way, its ability to generate long-term gains would be constrained.

Susquehanna also stands apart in how its taxes are prepared, ProPublica’s records show. Unlike his billionaire peers, Yass does not have his tax returns prepared by outside accountants. Instead, they’re prepared in-house at Susquehanna. Avoiding an outside accountant can offer more leeway in filing returns that test the boundaries of the law and might be challenged by the IRS later on, experts say. Several former employees told ProPublica that details of the firm’s tax strategy are closely guarded, even inside the company.

From 2013 to 2018, Griffin, Overdeck and Siegel paid average income tax rates ranging from 29% to 34%. (Representatives for the three men declined to comment.) Yass averaged 19%. ProPublica estimates that if Yass’ tax returns had resembled those of his competitors, he would have paid $1 billion more in federal income taxes during this period alone.

Yass does have one peer who achieved even lower tax rates and did so for years. Billionaire Jim Simons is one of the founders of Renaissance Technologies, one of the premier hedge funds known for high-frequency trading. His rates were often in the single digits between 2009 and 2018, never exceeding 14%. One reason Simons paid so little are deductions from charitable donations, averaging hundreds of millions of dollars each year; Yass doesn’t give nearly as much to charity. But another reason was Renaissance’s ability to create long-term gains over a decade.

That, however, didn’t last. A 2014 congressional investigation and IRS audit concluded the Renaissance scheme to generate such gains was illegal. Simons himself ultimately paid the IRS at least $670 million to resolve the case. Collectively, fund executives and investors paid an undisclosed amount, reportedly in the billions, in back taxes and penalties. A spokesperson for Simons declined to comment.

Having slashed his income tax bills, Yass has already taken steps to protect his fortune from the government for years to come.

He created special trusts designed to sidestep the estate tax when passing money to heirs at death, court records show. In using these grantor retained annuity trusts, or GRATs, Yass joins dozens of other billionaires, as ProPublica has reported.

That suggests that Yass’ adult children, two of whom work at Susquehanna, stand to someday inherit multibillion-dollar fortunes — tax-free.

Over decades of TV appearances and speeches promoting his libertarian gospel, Milton Friedman often liked to say he was “in favor of cutting taxes under any circumstances and for any excuse, for any reason, whenever it’s possible.” Friedman died in 2006. Today, Yass, who reveres the economist, is trying to bring Friedman’s ideas to fruition.

Yass has not only worked assiduously to lower his own taxes but has poured millions into political efforts to eliminate them for his class. In recent years he has given $32 million to the anti-tax stalwart Club for Growth. This money paid for TV ads attacking candidates who were seen as wobbly on Friedman’s tax-cuts-anytime-anywhere philosophy.

In Pennsylvania, where Yass is the richest person in the state and a kingmaker in local politics, his favored candidates have shaped tax policy. He is a longtime financial patron of a Democratic state senator, Anthony Williams, one of the creators of a pair of tax credits that allow companies to slash their state tax bills if they give money to private and charter schools. Susquehanna is, in turn, a major user of the tax credits. (Williams did not respond to requests for comment.)

The programs limited the state tax credits a single company could receive, but Yass and the others found a way to sidestep the limits. Yass, Dantchik and Greenberg simply applied for the tax credits through individual companies each had formed, the Philadelphia Inquirer reported in 2015. In all, the credits have saved Yass and the others at least $53 million in state taxes, records show.

Yass’ views on taxes, along with another stance inspired by Friedman, school privatization, seem to have informed his shifting opinion of Donald Trump.

Yass had opposed Trump during the 2016 Republican presidential primary, instead donating large sums to Rand Paul of Kentucky, the de facto leader of the party’s libertarian wing, and to Libertarian Party nominee Gary Johnson.

A week after Trump won the presidency that November, Yass took the stage at a theater in Philadelphia. Even though Trump had not been his candidate, Yass seemed to relish the long-odds election win, joking that those who “didn’t like Tuesday’s results” could move to Canada.

He used the rest of his remarks at the event, part of a local TED Talk-style series, to promote his passion for charter and private schools and attack Philadelphia teachers. “All we ever hear about is how underpaid they are and how abused they are,” Yass said. “Well, the shocking fact is that the average school teacher in Philadelphia with benefits makes $117,000 a year.” Yass acknowledged that a large chunk of that figure was from pension and health care costs. (That year, Yass made $1.26 billion, before benefits.)

Over the next four years, Trump delivered both a historic tax cut for the rich and an education secretary who was a champion of charter schools.

Yass has since backed a range of pro-Trump candidates. In Pennsylvania, he has poured money into this year’s Republican effort to take the open gubernatorial seat, which many expect, if successful, will lead to an abortion ban in the state. The Club for Growth also backed a losing candidate for the state’s open U.S. Senate seat, Kathy Barnette, whose campaign centered on her hard-line opposition to abortion, even in cases of rape. Yass is the second biggest donor to the Club (which did not return ProPublica’s requests for comment).

He is also the largest donor to the Rand Paul-affiliated Protect Freedom PAC, giving $2.5 million of his more than $12 million in recent donations just days after the 2020 election. The group’s website says of Democrats: “Of course, they stole the election.”

Yass is looking to harness discontent with public schools during the pandemic to push privatization of the system. He has given $15 million as the sole funder of a political action committee, the School Freedom Fund, that says “school closures, mask mandates, critical race theory, and more” have created “a unique opportunity to promote School Choice as the structural solution to dramatically improve education in America.”

If Yass came to politics motivated by his libertarian ideology, he now has an acute material reason — beyond taxes — to have a voice in Washington.

Late in the Trump administration, Susquehanna’s prize investment came under threat. President Trump announced on July 31, 2020, that he was considering banning TikTok in the United States. (Backers of the ban cited national security concerns over Americans’ private data being controlled by the Chinese firm behind the app, ByteDance.) Susquehanna's multibillion-dollar stake in ByteDance accounts for a major part of Yass’ fortune.

There’s no record of Yass having given to Trump before. But on Aug. 4, 2020, just a few days after the president’s TikTok announcement, Yass gave $5 million to the Club for Growth. Two days later, the group deviated from its normal practice of funding congressional races and announced an ad campaign in the presidential race: $5 million against Joe Biden. The group didn’t mention Yass, but the ads attacked Biden on Yass’ pet issue, charter schools. Later that month, Yass gave the group another $5 million, and more ads ran against Biden.

At the same time, Trump and other administration officials were personally involved in trying to broker a deal to avoid finalizing the TikTok ban. At one point in September, Trump publicly announced his support for a deal in which U.S. companies would buy stakes in ByteDance and a new board would be formed. Among the proposed members of the board: Dantchik, Yass’ partner at Susquehanna.

It’s not clear if Yass or Dantchik talked to the White House about the deal, which ultimately fell through. Courts later blocked the proposal to ban the app.

Yass hasn’t spoken much publicly about how he thinks about his engagement in politics. A rare glimpse came after the Jan. 6 riot, when a Philadelphia political activist named Laura Goldman emailed Yass to question his donations to the Club for Growth. One of the candidates the group backed, Sen. Josh Hawley, R-Mo., had objected to certifying the presidential election results just days earlier.

“To be clear — I don’t think the election was stolen,” Yass responded in a Jan. 15, 2021, email, first reported by the Guardian. “I gave the club money a year ago. Do you think anyone knew Hawley was going to do that? Sometimes politicians deceive their donors.”

Yass appears to have overcome any doubts about the Club for Growth, which has continued to back candidates who say the election was stolen.

Since he sent that email, he has given the group another $5.5 million.

Erik Prince threatens ProPublica reporters after they reveal special trusts he and others exploited to avoid estate taxes

by Jeff Ernsthausen, James Bandler, Justin Elliott and Patricia Callahan

ProPublica is a Pulitzer Prize-winning investigative newsroom. Sign up for The Big Story newsletter to receive stories like this one in your inbox.

Series: The Secret IRS Files

Inside the Tax Records of the .001%

It's well known, at least among tax lawyers and accountants for the ultrawealthy: The estate tax can be easily avoided by exploiting a loophole unwittingly created by Congress three decades ago. By using special trusts, a rarefied group of Americans has taken advantage of this loophole, reducing government revenues and fueling inequality.

There is no way for the public to know who uses these special trusts aside from when they've been disclosed in lawsuits or securities filings. There's also been no way to quantify just how much in estate tax has been lost to them, though, in 2013, the lawyer who pioneered the use of the most common one — known as the grantor retained annuity trust, or GRAT — estimated they may have cost the U.S. Treasury about $100 billion over the prior 13 years.

As Congress considers cracking down on GRATs and other trusts to help fund President Joe Biden's domestic agenda, a new analysis by ProPublica based on a trove of tax information about thousands of the wealthiest Americans sheds light on just how widespread the use of special trusts to dodge the estate tax has become.

More than half of the nation's 100 richest individuals have used GRATs and other trusts to avoid estate tax, the analysis shows. Among them: former Democratic presidential candidate Michael Bloomberg; Leonard Lauder, the son of cosmetics magnate Estée Lauder; Stephen Schwarzman, a founder of the private equity firm Blackstone; Charles Koch and his late brother, David, the industrialists who have underwritten libertarian causes and funded lobbying efforts to roll back the estate tax; and Laurene Powell Jobs, the widow of Apple founder Steve Jobs. (Powell Jobs' Emerson Collective is among ProPublica's largest donors.)

More than a century ago amid soaring inequality and the rise of stratospherically wealthy families such as the Mellons and Rockefellers, Congress created the estate tax as a way to raise money and clip the fortunes of the rich at death. Lawmakers later added a gift tax as a means of stopping wealthy people from passing their fortunes on to their children and grandchildren before death. Nowadays, 99.9% of Americans never have to worry about these taxes. They only hit individuals passing more than $11.7 million, or couples giving more than $23.4 million, to their heirs. The federal government imposes a roughly 40% levy on amounts above those figures before that wealth is passed on to heirs.

For her part, Powell Jobs has decried as “dangerous for a society" the early 20th century fortunes of the Mellons, Rockefellers and others. “I'm not interested in legacy wealth buildings, and my children know that," she told The New York Times last year. “Steve wasn't interested in that. If I live long enough, it ends with me."

Nonetheless, after the death of her husband in 2011, Powell Jobs used a series of GRATs to pass on around a half a billion dollars, estate-tax-free, to her children, friends and other family, according to the tax records and interviews with her longtime attorney. By using the GRATs, she avoided at least $200 million in estate and gift taxes.

Her attorney, Larry Sonsini, said Powell Jobs did this so that her children would have cash to pay estate taxes when she dies and they inherit “nostalgic and hard assets," such as real estate, art and a yacht. (At 260 feet, Venus is among the larger pleasure ships in the world.) Without the $500 million or so passed through the trusts, he said, Powell Jobs' heirs would have to sell stock that she intends to give to charity to pay her estate tax bill.

Sonsini said Powell Jobs, whose fortune is pegged at $21 billion by Forbes, has already given billions away to charity and paid $2.5 billion in state and federal taxes between 2012 and 2020. “When you look at an estate that may be worth multiple billions, and all the rest is going to charity, and you put it in perspective, what is the problem we're worried about here?" Sonsini asked. “This is not about creating dynasty wealth for these kids."

In a written statement, Powell Jobs said she supports “reforms that make the tax code more fair. Through my work at Emerson Collective and philanthropic commitments, I have dedicated my life and assets to the pursuit of a more just and equitable society."

Others whose special trusts ProPublica identified, including Bloomberg and the Kochs, declined to comment on why they'd set up the trusts or their estate-tax implications. Representatives for Lauder didn't respond to requests to accept questions on his behalf. Schwarzman's spokesperson wrote that he is “one of the largest individual taxpayers in the country and fully complies with all tax rules."

A typical GRAT entails putting assets, like stocks, in a trust that ultimately benefits a person's heirs. The trust pays back an amount equal to what the trust's creator put in plus a modest amount of interest. But any gains on the investments above that amount flow to the heirs free of gift or estate taxes. So if a person puts $100 million worth of stock in a GRAT and the stock rises in value to $130 million, their heirs would receive about $30 million tax-free.

In 1990, Congress accidentally created GRATs when it closed another estate tax loophole that was popular at the time. The IRS challenged the maneuver but lost in court.

“I don't blame the taxpayers who are doing it," said Daniel Hemel, a professor at the University of Chicago Law School. “Congress has virtually invited them to do it. I blame Congress for creating the monster and then failing to stop the monster once it became clear how much of the tax base the GRAT monster would eat up."

Users of the trusts extend well beyond the top of the Forbes rankings, ProPublica's analysis of the confidential IRS files show. Erik Prince, founder of the military contractor Blackwater and himself heir to an auto parts fortune, used the shelter. Fashion designer Calvin Klein has used them, as have “Saturday Night Live" creator Lorne Michaels and media mogul Oprah Winfrey.

“We have paid all taxes due," a spokesperson for Winfrey said. A representative of Klein did not accept questions from ProPublica or respond to messages. A spokesman for Michaels declined to comment.

Prince also did not answer questions. “Hey if you publish private information about me I'll be sure to return the favor," he wrote. “Go ahead and fuck off."

The GRAT has become so ubiquitous in recent decades that high-end tax lawyers consider it a plain vanilla strategy. “This is an off-the-shelf solution," said Michael Kosnitzky, co-leader of the private wealth practice at law firm Pillsbury Winthrop Shaw Pittman. “Almost every wealthy person should have one."

ProPublica's tally almost certainly undercounts the number of Forbes 100 members who use shelters to avoid estate taxes. ProPublica counted only those people whose tax records or public filings explicitly mention GRATs or other trusts commonly used to dodge gift and estate taxes. But a wealthy person can call their trusts whatever they want, leaving plenty of trusts outside of ProPublica's count.

This month, the House and Senate are hammering out proposals to raise revenue to help pay for the Biden administration's plans to expand the social safety net. The legislative blueprint released by House Ways and Means Committee Chairman Richard Neal, D-Mass., would defang GRATs and other trusts, which would still be legal but no longer be as useful for estate tax avoidance. If the provision makes it into law, “it would put a major dent in GRATs," said Bob Lord, an Arizona attorney who specializes in trusts and estates.

Senate Budget Committee Chairman Bernie Sanders, I-Vt., has proposed going further in undercutting estate tax avoidance tools. But the prospect of any reform is uncertain, as Democrats on Capitol Hill struggle to find the votes to pass the package of spending and tax changes.

GRATs are commonly described by tax lawyers as a “heads I win, tails we tie" proposition. If the investment placed in the GRAT soars in value, that increase passes to an heir without being subject to future estate tax. If the investment doesn't go up, the wealthy person can simply try again and again until they succeed, leading many users to have multiple GRATs going at a time.

For example, Herb Simon, founder of the country's biggest shopping mall empire and owner of the Indiana Pacers, was one of the most prolific GRAT creators in records reviewed by ProPublica. Since 2000, he has hatched dozens of the trusts, often more than one a year. In an interview with The Indianapolis Star in 2017, the octogenarian Simon said, “It's always a big tax problem" for the next generation when someone dies, “but we've worked that tax problem. We won't have a problem with that."

A spokesperson for Simon didn't respond to questions for this article.

Mentions of these trusts have periodically surfaced in the press after being disclosed in securities filings, as was the case with trusts held by Facebook co-founders Mark Zuckerberg and Dustin Moskovitz and Chief Operating Officer Sheryl Sandberg. In 2013, Bloomberg News published a groundbreaking series on GRATs, mining securities filings and other records to reveal how the mega-rich, including casino magnate Sheldon Adelson and such families as Walmart's Waltons, had perfected the use of the device.

ProPublica's data shows that Michael Bloomberg, the majority owner of the company that bears his name and No. 13 on Forbes' list of the wealthiest Americans, is himself a heavy user of GRATs. Over the course of a dozen years, he repeatedly cycled pieces of his private company in and out of the trusts — often opening multiple GRATs in one year. During that time, hundreds of millions of dollars in income flowed through Bloomberg's GRATs, giving him opportunities to shield parts of his fortune for his heirs.

ProPublica described the transactions (but not the name of the person engaging in them) to Lord, the trusts and estates attorney. The GRAT is “the perfect loophole to avoid estate and gift tax in this situation," said Lord, who is also tax counsel for Americans for Tax Fairness and an advocate for estate tax reform.

When Bloomberg ran for president in 2020, he vowed to shore up the estate tax. “Owners of the biggest estates are expert at gaming the system to reduce what they owe," a campaign fact sheet for his tax plan said. Bloomberg vowed to “lower the estate-tax threshold, so that more estates are taxed," and to “shut down multiple estate-tax avoidance schemes." His fact sheet offered few details as to how he would do that, and it didn't mention GRATs.

The legislation Congress is now considering to curtail GRATs would leave open other options for estate tax avoidance, including a cousin to the GRAT known as a charitable lead annuity trust, or CLAT, which contributes to charity while passing gains from stocks and other assets on to heirs. And the legislation would grandfather in existing trusts, meaning that those who have already established trusts would be able to continue to use them to avoid paying estate taxes.

That has set off a predictable push by tax lawyers to get their clients to create tax-sheltering trusts before any new legislation takes effect.

Porter Wright, a law firm that offers estate planning services, told existing and potential clients it was “critical" to evaluate opportunities because “the window may close very soon. There are important and time sensitive issues which could substantially impact the amount of wealth you are able to transfer free of estate and gift tax to future generations."

A House bill would blow up a tool of the superwealthy to avoid taxes

This was first published by ProPublica, a Pulitzer Prize-winning investigative newsroom. Sign up for The Big Story newsletter to receive stories like this one in your inbox.

Legislation currently making its way through Congress would take a sledgehammer to the massive individual retirement accounts built up tax-free by a select group of the ultrawealthy.

The proposal, which is part of the infrastructure and tax package advancing in the House, targets the jaw-dropping IRAs accumulated by multimillionaires and billionaires such as tech investor Peter Thiel, which were first reported by ProPublica earlier this year. Those accounts — Thiel's alone was worth $5 billion in 2019 — have allowed some super-wealthy Americans to turn their Roth IRAs, tools meant to incentivize middle-class retirement saving, into supersized tax shelters.

The proposed reform, put forward by House Ways and Means Chairman Richard Neal, D-Mass., would effectively cap the total amount someone could hold in a Roth at $20 million and compel the holders of the giant accounts to withdraw anything over that limit. Separately, individuals would have to add up the balances of their retirement accounts — including Roths, traditional IRAs, 401(k)s and 403(b)s — and every year withdraw half of any amount over $10 million. The provisions would only apply to individuals with taxable income of over $400,000 or couples making over $450,000.

The reform wouldn't affect the overwhelming majority of Americans, whose retirement savings (if they have any) are far more modest — the average Roth was worth just $39,108 at the end of 2018.

“Incentives in our tax code that help Americans save for retirement were never intended to enable a tax shelter for the ultra-wealthy," Neal said earlier this year. “We must shut down these practices."

Should the bill pass, it could have profound implications for PayPal founder Thiel, whose gargantuan Roth stunned lawmakers, spurring Neal to vow a crackdown. Thiel wouldn't owe any tax up front and no early withdrawal penalties would apply, but he'd be required to move billions out of the tax-advantaged account. And any gains on investments made with that money would no longer be sheltered from taxes, potentially creating hundreds of millions of dollars in future tax liabilities.

The great appeal of the Roth IRA is that once money is inside it, any income generated — such as capital gains from selling a stock, investment interest or dividends — is tax-free, as long as the holder waits until he or she is 59 and a half to withdraw it. (Thiel hits that mark in 2027.) In a traditional IRA, by contrast, money that's withdrawn counts as income and is taxed.

The IRA reforms are part of a slate of proposals designed to eliminate loopholes and boost tax rates on rich individuals and corporations.

Several of the changes address revelations contained in The Secret IRS Files, a series of ProPublica stories published this year that are exploring the ways the very richest Americans avoid paying taxes. Usually such efforts remain secret, but ProPublica has obtained a trove of tax records covering thousands of the country's richest people. The records reveal not only the diverse array of tax-avoidance techniques used by the rich, but also that some of the very richest have consistently found ways to avoid taking income, so they pay little or no taxes, even as their wealth multiplied to historic levels.

The current House plan falls short of President Joe Biden's more ambitious proposals to combat wealth inequality through the tax code. But experts say it would significantly increase the taxes paid by high-income Americans. Among other things, it would all but eliminate a major deduction created by President Donald Trump's 2017 tax law that, as ProPublica recently reported, showered massive tax breaks on some of the richest families in the country.

Given the stakes for a small group of wealthy and powerful Americans, it's unclear whether the IRA proposal, along with the rest of the package, will become law. It must pass the House and make it through the Senate, where it will likely need the votes of all 50 Democratic senators to pass. Capitol Hill staffers say the bill remains fluid and provisions could still be cut, added or modified.

For now, however, the proposal has alarmed those who stand to lose the most. Three tax lawyers told ProPublica that clients with giant IRAs have reached out to them, worried about the potential reforms. Already a lawyer and an accountant are offering a paid webinar that pitches strategies to help owners of large IRAs get around the proposed rules.

A spokesman for Thiel didn't respond to a request for comment.

The tax proposals have drawn opposition from Republicans on Capitol Hill. “This is very bad news for the U.S. economy," said Ways and Means Committee ranking member Rep. Kevin Brady, R-Texas, in an interview this week.

A budget analyst at the anti-tax Heritage Foundation specifically criticized the IRA reform proposals as “stifling retirement savings and decreasing the economy-wide investment in future productivity."

Neal announced his plans to curb the size of mega IRAs in July following ProPublica's story revealing how Thiel and other billionaires had amassed giant retirement accounts using techniques largely unavailable to most taxpayers. Other wealthy investors with giant retirement accounts included financier Michael Milken, Warren Buffett and executives from investment giant Bain Capital.

Neal joined his Senate counterpart, Ron Wyden, D-Ore., who had been pushing for reform of mega IRAs for years without much support from his peers.

With a multibillion-dollar tax-free account on the line, a wealthy investor might try to keep his income below the $400,000 threshold set by the proposal. In Thiel's case, it's not clear if that would be possible, given that he's long reported tens of millions of dollars on his tax returns from capital gains, interest and dividends on investments he holds outside of his Roth IRA. And even if he has to withdraw billions from his Roth, he will never have to pay taxes on years of growth inside the account.

ProPublica has previously reported that several billionaires have had very little taxable income in certain years, including Jeff Bezos and Elon Musk. Musk did not respond to questions for that story and Bezos' representatives would not designate someone to accept questions related to that story.

The proposal would also add restrictions in areas that congressional investigators have said are ripe for abuse by the wealthy: The owners of IRAs would be barred from using the accounts to either purchase certain nonpublic investments or buy stakes in companies in which they are an officer.

Thiel launched his Roth IRA by purchasing so-called founder's shares of PayPal in 1999 when he was chairman and CEO of the company, according to tax records and a financial statement Thiel included in his application for residency in New Zealand. Securities and Exchange Commission records show he bought 1.7 million shares for $1,700, or a tenth of a penny per share. (The maximum contribution to a Roth that year was $2,000.) PayPal later told the SEC the shares were sold “below market value."

The practice has become popular among the founders of Silicon Valley companies, who tuck shares of their startups into IRAs, often after buying them at bargain prices. This can sidestep IRA contribution limits and generate massive tax-free growth if the value of their companies explodes.

The proposal would also shut down the so-called backdoor Roth. ProPublica found that billionaires like Buffett had taken advantage of a maneuver, known as a conversion, that allows the wealthy to sidestep existing income caps to create a Roth IRA. In a conversion, the owner of a traditional IRA can transform it into a Roth by paying one-time tax on the money. Once the account is converted into a Roth, no additional income taxes are ever due. The new provision would bar conversions for individuals with income over $400,000, though the ban would not go into effect until 2031 for budgetary reasons. (Buffett previously didn't respond to questions about his IRA.)

The proposal also has implications for the holders of giant traditional IRAs, who could suddenly owe a hefty tax bill. Money withdrawn from a traditional IRA counts as taxable income. Milken, the 1980s junk bond king who went to prison for fraud and was later pardoned by Trump, had traditional IRAs valued at $509 million at the end of 2018, according to tax records. If the law passed, Milken could face a tax bill of roughly $100 million, depending on the current size of his account. A spokesperson for Milken declined to comment.

Separately, another part of the bill would tackle the generous business income deductions granted by Trump's 2017 tax law.

As ProPublica previously reported, the drafting of the deduction was marked by last-minute changes and a rush of lobbying dollars from corporations and the superrich. The result of its passage, confidential tax records show, was a windfall for billionaires such as media mogul Michael Bloomberg, packaging tycoons Dick and Liz Uihlein, and the Bechtel family, owners of a global engineering and construction firm.

Bloomberg received a deduction of roughly $183 million in 2018 alone as a result of the provision, while the Uihleins netted around $118 million.

Under the House proposal, the deduction would be capped at $400,000 for an individual and $500,000 for a couple, virtually wiping it out for the very rich. If such a cap had been in place in 2018, for example, the Uihleins would have gotten a deduction worth just $500,000 instead of $118 million. A competing Senate proposal unveiled by Wyden in July would go even further. A spokesperson for the Uihleins declined to comment on the proposed reforms.

On a broader level, the House plan would spell a significant tax hike on Americans earning more than $400,000, raising their individual income tax rates as well as bumping up the corporate tax rate, the first such hikes in a decade.

But despite the proposal's ambition, critics say it misses a rare opportunity to capture the massive untaxed wealth of some of the richest individuals in history, including Bezos and Musk, who have often found ways to keep their income low.

As ProPublica reported, they and other billionaires have managed to pay little to no taxes in the past. Some have done so by pursuing the so-called buy, borrow, die strategy. By holding on to his Tesla stock but borrowing money to finance his lifestyle, Musk, for example, can avoid income that is taxable under current law. If he sticks to this strategy till death, the income tax liability on his fortune will evaporate for his heirs.

Some Democrats and policymakers had aspired to even bolder tax code changes that would have targeted the stratospheric increases in the ultrawealthy's riches. One idea, championed by Sens. Elizabeth Warren, D-Mass., and Bernie Sanders, I-Vt., would be to levy a so-called wealth tax on billionaires' overall holdings. Another, pushed by Wyden, would tax the annual gains billionaires logged, even if they hadn't sold the assets. Both ideas foundered, with concerted opposition from billionaires and skittishness from Democratic centrists. Some critics point out that wealth taxes have often failed in other countries. And many policymakers believe it would be too logistically difficult to measure assets properly and enforce such a sweeping rule on gains.

How Trump's tax law opened a loophole that let executives cash in big time

This story was first published by ProPublica, a Pulitzer Prize-winning investigative newsroom. Sign up for The Big Story newsletter to receive stories like this one in your inbox.

In the months after President Donald Trump signed the Tax Cuts and Jobs Act in December 2017, some tax professionals grew giddy as they discovered opportunities for their clients inside a law that already slashed rates for corporations and wealthy individuals.

At a May 2018 conference of financial advisers, one wealth planner told the room that a key provision of the new law “leaves a gaping hole in the tax code." As he put it, “The goal by the end of the presentation today is to make you guys the bus drivers, or the truck drivers, to drive right through that hole with your clients."

Among the tax-saving opportunities offered by the law: Taxes on profits from certain types of businesses were cut dramatically, while the rate on salaries those businesses paid was reduced only slightly.

That created an alluring opportunity. People who were both owners and employees of a company could make the same amount of money but change how they label it, by lowering their salaries and in turn increasing the company's profits, which they shared in. That would reduce their tax bill by moving money from a high-tax category to a lower one: Wages are taxed at a top rate of 37% plus an additional 3.8% Medicare levy, while profits, under the new law, are taxed at a top rate of 29.6% (with no Medicare tax). Proponents of this provision claimed it would foster increased investment in American businesses (economists say it's too early to determine whether that's true). But even before the bill passed, prominent tax academics warned, in an article titled “The Games They Will Play," that the tax break would be abused.

Their fears appear to have materialized. Secret IRS data shows multiple instances in which salaries for top executives and owners suddenly and inexplicably dropped in the first year after the Trump tax cut, reducing their tax bills even as their companies appeared to thrive. The mysterious pay cuts played out across industries, from logistics companies to real estate firms to makers of bathtubs, and among executives of varying degrees of prominence. The salary for one construction firm executive dropped from more than $4 million in 2017 to $105,000 in 2018.

The wages for car accessory manufacturer David MacNeil, whose WeatherTech floor mats are featured in a Super Bowl ad each year, fell from $68 million in 2017 to $47 million in 2018.

The salary of Jeffrey Records, CEO of Oklahoma City-based MidFirst Bank, plummeted from $8.6 million to $1.8 million.

And the wages of Dick Uihlein, the Republican megadonor and chairman of shipping supplies behemoth Uline, sank from $5.1 million to $2.1 million.

It's impossible to say how much money was reclassified as a result of the new law, but consider this: The loophole already existed, in much smaller form, before the Trump tax overhaul. A government report in 2009 estimated the U.S. Treasury was losing billions to this strategy. Back then, an owner could save the Medicare tax by counting a dollar as profits rather than salary. But after the Trump law, the tax savings roughly tripled, to about 11%.

The revelations about the wage maneuvers come from a trove of IRS records obtained by ProPublica covering thousands of the wealthiest Americans. Previous articles in “The Secret IRS Files" series have detailed how the wealthy avoid paying taxes legally, including a story last week exploring the massive benefits the Trump tax overhaul provided billionaires.

The sudden shifts in compensation revealed in the tax returns of wealthy business owners show how they may be gaming federal law to further slash their taxes. They also highlight how, unlike most Americans, whose taxes are automatically taken out of each paycheck, wealthy business owners have a menu of avoidance techniques afforded to them by the tax code.

The tax benefits of shifting wages to profits can be significant. MacNeil, for example, saved an estimated $8 million in the first two years, according to a ProPublica analysis of the IRS records.

MacNeil defended his wage drop and said he used the tax savings to create more jobs: “You want me investing in my country — my fellow Americans? Get out of my pocket."

ProPublica analyzed years of wage and profit data and found that for each of the companies named in this story, company profits rose even as wages were cut.

Unlike publicly traded corporations, private companies are not required to publicly report profits, salaries for top executives or their rationales for compensation decisions. But experts who spoke to ProPublica said that, if audited, these executives would have to justify why the value of their labor plunged in a given year. The secret tax data does not answer that question.

Taking an unreasonably low salary in order to avoid taxes is illegal. But the IRS' definition of “reasonable" is vague, and the vast majority of business owners will likely never have to justify the salary cuts. Only a tiny fraction of such companies have their salaries examined by the IRS. Karen Burke, a tax law professor at the University of Florida, said, “For a business owner, there's every incentive to do this and every reason to believe you'll get away with it."

David MacNeil enjoys being the boss. A table reserved for him at the cafeteria of his sprawling production plant has a placard that warns: “Don't even think about sitting here." He compliments one of his 1,700 employees about the company pickup truck he's driving, then adds, “It's mine." As he walks among the whirring machines pumping out his custom car mats, he revels in the fact that he built a flourishing manufacturing empire without offshoring, creating hundreds of jobs.

“This is why they give us a tax break," he said, “so we can make shit happen."

After ProPublica contacted him, MacNeil invited two reporters for a daylong tour of his factory complex in Bolingbrook, Illinois. A former car salesman, he founded WeatherTech, a top U.S. manufacturer of car accessories, in 1989 and now regularly generates $100 million in annual profit. MacNeil owns a super-yacht, a private jet, a Florida equestrian estate and a collection of antique cars.

He describes himself as “the kind of man America needs, a man that believes in the great American worker." As he led the tour of his plant, he took his phone out to read emails from employees praising his generosity and showed photos of himself removing trash from the ocean in his free time.

MacNeil backed Trump, donating $1 million to his inauguration and hundreds of thousands to Republican candidates and causes. Trump's tax law would have cut the magnate's taxes no matter what. But the IRS records indicate MacNeil may have taken steps to further boost those savings.

For 16 years, the records show, MacNeil's wages climbed every year: from $1.1 million in 2008 to $10.1 million in 2012 and almost $68 million in 2017. But in 2018, that trend suddenly reversed. He cut his salary to $47 million. Then in 2019, he slashed it even more aggressively, bringing it down to $17 million — 75% lower than two years earlier.

MacNeil's CEO title hadn't changed. He hadn't stepped back. “I bust my ass seven days a week," he said.

As MacNeil's salary fell, the company's profits, which are taxed at a lower rate, surged. In 2018, after four years in which profits hovered around $100 million a year, they suddenly jumped to $121 million. The $21 million increase mirrored the amount that MacNeil lowered his wages that year.

With his (higher-taxed) wages dropping and his (lower-taxed) profits rising, MacNeil avoided an estimated $8 million in taxes.

MacNeil first said he was unaware that his wages had been cut 75% until ProPublica asked him about it. “I had no idea," he said, asserting the decision was made by his accountants. Later, MacNeil told ProPublica that his wage decrease stemmed from his decision to begin reinvesting almost all of his profits back into the company, leaving him less cash to pay himself in wages.

Experts told ProPublica that increased capital investments by an owner could help justify lower wages, if they result in the owner having less cash left over.

Still, the tax data shows MacNeil's profits soaring during the years his wages dropped. The data does not indicate how much money MacNeil put back into the business. Asked to provide specific figures outlining his annual cash flow and reinvestment, MacNeil declined.

MacNeil also cited the vagueness of the IRS' definition of “reasonable compensation." Most important, he said, the estimated $8 million in taxes he avoided by dropping his wages allowed him to buy an $8 million machine that would generate many multiples of that in tax revenue in the years to come, because it would make his business more profitable.

In a series of text messages in the days that followed, MacNeil continued to defend himself, telling a ProPublica reporter that he didn't understand “the real world" and “it's time to grow up and get a real job."

“Break it up anyway you want, you saw there was a half billion dollars in investment with your own eyes," he wrote. “We've paid hundreds and hundreds of millions of dollars in taxes since 2012. How much have you paid? Chump change for sure. Enjoy!"

MacNeil's company, like all of the ones discussed in this article, is organized as a pass-through, a tax structure that is quite common but not popularly understood.

To understand pass-throughs, it's first useful to know how their corporate cousin, the C corporation, is taxed. Most large publicly traded companies, the ExxonMobils and Nikes of the world, are C corporations. When these companies end the year, they must pay the IRS corporate income tax on any profits they have earned. Shareholders receive money, and then owe taxes, only if they decide to sell their holding at a gain or if the companies issue a dividend.

Most businesses in the U.S. are not C corporations, but pass-throughs. They include everything from a small corner deli to a hedge fund to a multinational construction company. Most are privately held. When one of these businesses makes a profit, they do not pay the corporate tax. Instead, that money “passes through" directly to the owner and is reflected on the owners' personal tax returns. It is therefore taxed only once, and individual income tax rates apply.

One popular type of pass-through is called an S corporation, named after the section in the tax code. They were created in the Eisenhower era as an option for small businesses who wanted to face only a single layer of tax. Since then, many large companies have structured themselves as S corporations for the tax benefits they can bring.

The IRS requires that S corporations pay reasonable salaries — they “should not attempt to avoid paying employment taxes by having their officers treat their compensation as cash distributions" — but the agency has been vague about what those words mean. Factors cited for what makes a salary reasonable include the individual's training and experience, job responsibilities and what comparable businesses pay for similar roles.

To offer more clarity, the IRS has publicly cited court cases it fought against business owners. In one, from 2001, a Pennsylvania veterinarian took all of his compensation as business income, paying himself no wages even though he spent more than 30 hours a week doing surgeries and other tasks. The veterinarian lost and was forced to pay back taxes.

In another case, an Iowa accountant was paid a salary of $24,000 a year, while taking profits of about $200,000. The accountant, David Watson, specialized in advising clients on tax issues involving pass-through companies. The court ruled against Watson, forcing him to pay back taxes and penalties, after it found that the market rate for his services at the time would have been over $90,000.

The issue has at times become a more public flashpoint. Former Democratic presidential nominee John Edwards was criticized for taking a small salary from the law practice he owned, and former Republican House Speaker Newt Gingrich took heat for doing the same from companies he created that profit from his speeches and other appearances. More recently, The Wall Street Journal reported that Joe Biden exploited the tactic in the years before he became president with his book and speech income. Gingrich, Edwards and Biden have all defended their handling of their tax affairs.

A 2009 report from the Government Accountability Office estimated that in 2003 and 2004, about 13% of S corporations paid artificially low wages, resulting in about $3 billion in lost tax revenue. IRS officials complained to investigators that making the case that a salary is artificially low can be difficult and time consuming. From 2006 to 2008, the IRS examined only 0.5% of S corporations, and in less than a fourth of those cases was compensation looked at. By 2019, the audit rate for S corporations had fallen even lower, to 0.2%.

As the Trump tax cut was being hammered out, lobbyists for industry groups and specific companies pushed to make sure they were eligible. Engineering, real estate and manufacturing were granted the deduction. Lawyers and companies performing “financial services," for example, were not.

Despite that, banks lobbied successfully to be eligible for the deduction. One of the banks that pushed for that eligibility was MidFirst. That year, even as the CEO's salary dropped from $8.6 million to $1.8 million, his share of the profits jumped more than $16 million. In 2019, Records' salary rebounded to $6.5 million, but it remained lower than it had been in the year before the Trump tax law.

Representatives for Records declined to answer questions for this article.

Dick and Liz Uihlein also appear to have benefited. The co-founders of Uline gave millions to support Sen. Ron Johnson, the Wisconsin Republican who became the champion of the pass-through provision in the Trump tax overhaul.

Before the law passed, the salaries for the Uihleins had fluctuated. But in 2018 they dropped dramatically, from a total of $10.5 million to $4.2 million. Their wages had not been that low in more than a decade.

The business reasons for the pay cut are not clear from the available records, and a spokesman for the Uihleins declined to answer questions from ProPublica. Dick remained chairman, and Liz was president. Liz Uihlein said publicly in 2020 that the couple was still heavily involved in running the company.

Their business was booming in the year their wages fell. Profits rose from about $721 million in 2017 to $937 million in 2018, ProPublica's analysis of the company's tax data shows. The company remained North America's leading distributor of shipping and packaging supplies. “Business is great," Uline's Chief Human Resources Officer Gil De Las Alas told the Kenosha News in November 2018. “We just keep growing, growing, growing."

Secret IRS files reveal how much the ultrawealthy gained by shaping Trump's 'big, beautiful tax cut'

ProPublica is a Pulitzer Prize-winning investigative newsroom. Sign up for The Big Story newsletter to receive stories like this one in your inbox.

Series: The Secret IRS Files

Inside the Tax Records of the .001%

In November 2017, with the administration of President Donald Trump rushing to get a massive tax overhaul through Congress, Sen. Ron Johnson stunned his colleagues by announcing he would vote “no."

Making the rounds on cable TV, the Wisconsin Republican became the first GOP senator to declare his opposition, spooking Senate leaders who were pushing to quickly pass the tax bill with their thin majority. “If they can pass it without me, let them," Johnson declared.

Johnson's demand was simple: In exchange for his vote, the bill must sweeten the tax break for a class of companies that are known as pass-throughs, since profits pass through to their owners. Johnson praised such companies as “engines of innovation." Behind the scenes, the senator pressed top Treasury Department officials on the issue, emails and the officials' calendars show.

Within two weeks, Johnson's ultimatum produced results. Trump personally called the senator to beg for his support, and the bill's authors fattened the tax cut for these businesses. Johnson flipped to a “yes" and claimed credit for the change. The bill passed.

The Trump administration championed the pass-through provision as tax relief for “small businesses."

Confidential tax records, however, reveal that Johnson's last-minute maneuver benefited two families more than almost any others in the country — both worth billions and both among the senator's biggest donors.

Dick and Liz Uihlein of packaging giant Uline, along with roofing magnate Diane Hendricks, together had contributed around $20 million to groups backing Johnson's 2016 reelection campaign.

The expanded tax break Johnson muscled through netted them $215 million in deductions in 2018 alone, drastically reducing the income they owed taxes on. At that rate, the cut could deliver more than half a billion in tax savings for Hendricks and the Uihleins over its eight-year life.

But the tax break did more than just give a lucrative, and legal, perk to Johnson's donors. In the first year after Trump signed the legislation, just 82 ultrawealthy households collectively walked away with more than $1 billion in total savings, an analysis of confidential tax records shows. Republican and Democratic tycoons alike saw their tax bills chopped by tens of millions, among them: media magnate and former Democratic presidential candidate Michael Bloomberg; the Bechtel family, owners of the engineering firm that bears their name; and the heirs of the late Houston pipeline billionaire Dan Duncan.

Usually the scale of the riches doled out by opaque tax legislation — and the beneficiaries — remain shielded from the public. But ProPublica has obtained a trove of IRS records covering thousands of the wealthiest Americans. The records have enabled reporters this year to explore the diverse menu of options the tax code affords the ultrawealthy to avoid paying taxes.

The drafting of the Trump law offers a unique opportunity to examine how the billionaire class is able to shape the code to its advantage, building in new ways to sidestep taxes.

The Tax Cuts and Jobs Act was the biggest rewrite of the code in decades and arguably the most consequential legislative achievement of the one-term president. Crafted largely in secret by a handful of Trump administration officials and members of Congress, the bill was rushed through the legislative process.

As draft language of the bill made its way through Congress, lawmakers friendly to billionaires and their lobbyists were able to nip and tuck and stretch the bill to accommodate a variety of special groups. The flurry of midnight deals and last-minute insertions of language resulted in a vast redistribution of wealth into the pockets of a select set of families, siphoning away billions in tax revenue from the nation's coffers. This story is based on lobbying and campaign finance disclosures, Treasury Department emails and calendars obtained through a Freedom of Information Act lawsuit, and confidential tax records.

For those who benefited from the bill's modifications, the collective millions spent on campaign donations and lobbying were minuscule compared with locking in years of enormous tax savings.

A spokesperson for the Uihleins declined to comment. Representatives for Hendricks didn't respond to questions. In response to emailed questions, Johnson did not address whether he had discussed the expanded tax break with Hendricks or the Uihleins. Instead, he wrote in a statement that his advocacy was driven by his belief that the tax code “needs to be simplified and rationalized."

“My support for 'pass-through' entities — that represent over 90% of all businesses — was guided by the necessity to keep them competitive with C-corporations and had nothing to do with any donor or discussions with them," he wrote.

By the summer of 2017, it was clear that Trump's first major legislative initiative, to “repeal and replace" Obamacare, had gone up in flames, taking a marquee campaign promise with it. Looking for a win, the administration turned to tax reform.

“Getting closer and closer on the Tax Cut Bill. Shaping up even better than projected," Trump tweeted. “House and Senate working very hard and smart. End result will be not only important, but SPECIAL!"

At the top of the Republican wishlist was a deep tax cut for corporations. There was little doubt that such a cut would make it into the final legislation. But because of the complexity of the tax code, slashing the corporate tax rate doesn't actually affect most U.S. businesses.

Corporate taxes are paid by what are known in tax lingo as C corporations, which include large publicly traded firms like AT&T or Coca-Cola. Most businesses in the United States aren't C corporations, they're pass-throughs. The name comes from the fact that when one of these businesses makes money, the profits are not subject to corporate taxes. Instead, they “pass through" directly to the owners, who pay taxes on the profits on their personal returns. Unlike major shareholders in companies like Amazon, who can avoid taking income by not selling their stock, owners of successful pass-throughs typically can't avoid it.

Pass-throughs include the full gamut of American business, from small barbershops to law firms to, in the case of Uline, a packaging distributor with thousands of employees.

So alongside the corporate rate cut for the AT&Ts of the world, the Trump tax bill included a separate tax break for pass-through companies. For budgetary reasons, the tax break is not permanent, sunsetting after eight years.

Proponents touted it as boosting “small business" and “Main Street," and it's true that many small businesses got a modest tax break. But a recent study by Treasury economists found that the top 1% of Americans by income have reaped nearly 60% of the billions in tax savings created by the provision. And most of that amount went to the top 0.1%. That's because even though there are many small pass-through businesses, most of the pass-through profits in the country flow to the wealthy owners of a limited group of large companies.

Tax records show that in 2018, Bloomberg, whom Forbes ranks as the 20th wealthiest person in the world, got the largest known deduction from the new provision, slashing his tax bill by nearly $68 million. (When he briefly ran for president in 2020, Bloomberg's tax plan proposed ending the deduction, though his plan was generally friendlier to the wealthy than those of his rivals.) A spokesperson for Bloomberg declined to comment.

Johnson's intervention in November 2017 was designed to boost the bill's already generous tax break for pass-through companies. The bill had allowed for business owners to deduct up to 17.4% of their profits. Thanks to Johnson holding out, that figure was ultimately boosted to 20%.

That might seem like a small increase, but even a few extra percentage points can translate into tens of millions of dollars in extra deductions in one year alone for an ultrawealthy family.

The mechanics are complicated but, for the rich, it generally means that a business owner gets to keep an extra 7 cents on every dollar of profit. To understand the windfall, take the case of the Uihlein family.

Dick, the great-grandson of a beer magnate, and his wife, Liz, own and operate packaging giant Uline. The logo of the Pleasant Prairie, Wisconsin, firm is stamped on the bottom of countless paper bags. Uline produced nearly $1 billion in profits in 2018, according to ProPublica's analysis of tax records. Dick and Liz Uihlein, who own a majority of the company, reported more than $700 million in income that year. But they were able to slash what they owed the IRS with a $118 million deduction generated by the new tax break.

Liz Uihlein, who serves as president of Uline, has criticized high taxes in her company newsletter. The year before the tax overhaul, the couple gave generously to support Trump's 2016 presidential campaign. That same year, when Johnson faced long odds in his reelection bid against former Sen. Russ Feingold, the Uihleins gave more than $8 million to a series of political committees that blanketed the state with pro-Johnson and anti-Feingold ads. That blitz led the Milwaukee Journal Sentinel to dub the Uihleins “the Koch brothers of Wisconsin politics."

Johnson's campaign also got a boost from Hendricks, Wisconsin's richest woman and owner of roofing wholesaler ABC Supply Co. The Beloit-based billionaire has publicly pushed for tax breaks and said she wants to stop the U.S. from becoming “a socialistic ideological nation."

Hendricks has said Johnson won her over after she grilled him at a brunch meeting six years earlier. She gave about $12 million to a pair of political committees, the Reform America Fund and the Freedom Partners Action Fund, that bought ads attacking Feingold.

In the first year of the pass-through tax break, Hendricks got a $97 million deduction on income of $502 million. By reducing the income she owed taxes on, that deduction saved her around $36 million.

Even after Johnson won the expansion of the pass-through break in late 2017, the final text of the tax overhaul wasn't settled. A congressional conference committee had to iron out the differences between the Senate and House versions of the bill.

Sometime during this process, eight words that had been in neither the House nor the Senate bill were inserted: “applied without regard to the words 'engineering, architecture.'"

With that wonky bit of legalese, Congress smiled on the Bechtel clan.

The Bechtels' engineering and construction company is one of the largest and most politically connected private firms in the country. With surgical precision, the new language guaranteed the Bechtels a massive tax cut. In previous versions of the bill, construction would have been given a tax break, but engineering was one of the industries excluded from the pass-through deduction for reasons that remain murky.

When the bill, with its eight added words, took effect in 2018, three great-great-grandchildren of the company's founder, CEO Brendan Bechtel and his siblings Darren and Katherine, together netted deductions of $111 million on $679 million in income, tax records show.

And that's just one generation of Bechtels. The heirs' father, Riley, also holds a piece of the firm, as does a group of nonfamily executives and board members. In all, Bechtel Corporation produced around $2.3 billion of profit in 2018 alone — the vast majority of which appears to be eligible for the 20% deduction.

Who wrote the phrase — and which lawmaker inserted it — has been a much-discussed mystery in the tax policy world. ProPublica found that a lobbyist who worked for both Bechtel and an industry trade group has claimed credit for the alteration.

In the months leading up to the bill's passage in 2017, Bechtel had executed a full-court press in Washington, meeting with Trump administration officials and spending more than $1 million lobbying on tax issues.

Marc Gerson, of the Washington law firm Miller & Chevalier, was paid to lobby on the tax bill by both Bechtel and the American Council of Engineering Companies, of which Bechtel is a member. At a presentation for the trade group's members a few weeks after Trump signed the bill into law, Gerson credited his efforts for the pass-through tax break, calling it a “major legislative victory for the engineering industry." Gerson did not respond to a request for comment.

Bechtel's push was part of a long history of lobbying for tax breaks by the company. Two decades ago, it even hired a former IRS commissioner as part of a successful bid to get “engineering and architectural services" included in one of President George W. Bush's tax cuts.

The company's lobbying on the Trump tax bill, and the tax break it received, highlight a paradox at the core of Bechtel: The family has for years showered money on anti-tax candidates even though, as The New Yorker's Jane Mayer has written, Bechtel “owed almost its entire existence to government patronage." Most famous for being one of the companies that built the Hoover Dam, in recent years it has bid on and won marquee federal projects. Among them: a healthy share of the billions spent by American taxpayers to rebuild Iraq after the war. The firm recently moved its longtime headquarters from San Francisco to Reston, Virginia, a hub for federal contractors just outside the Beltway.

A spokesperson for Bechtel Corporation didn't respond to questions about the company's lobbying. The spokesperson, as well as a representative of the family's investment office, didn't respond to requests to accept questions about the family's tax records.

Brendan Bechtel has emerged this year as a vocal critic of President Joe Biden's proposal to pay for new infrastructure with tax hikes.

“It's unfair to ask business to shoulder or cover all the additional costs of this public infrastructure investment," he said on a recent CNBC appearance.

As the landmark tax overhaul sped through the legislative process, other prosperous groups of business owners worried they would be left out. With the help of lobbyists, and sometimes after direct contact with lawmakers, they, too, were invited into what Trump dubbed his “big, beautiful tax cut."

Among the biggest winners during the final push were real estate developers.

The Senate bill included a formula that restricted the size of the new deduction based on how much a pass-through business paid in wages. Congressional Republicans framed the provision as rewarding businesses that create jobs. In effect, it meant a highly profitable business with few employees — like a real estate developer — wouldn't be able to benefit much from the break.

Developers weren't happy. Several marshaled lobbyists and prodded friendly lawmakers to turn things around.

At least two of them turned to Johnson.

“Dear Ron," Ted Kellner, a Wisconsin developer, and a colleague wrote in a letter to Johnson. “I'm concerned that the goal of a fair, efficient and growth oriented tax overhaul will not be achieved, especially for private real estate pass-through entities."

Johnson forwarded the letter from Kellner, a political donor of his, to top Republicans in the House and Senate: “All, Yesterday, I received this letter from very smart and successful businessmen in Milwaukee," adding that the legislation as it stood gave pass-throughs “widely disparate, grossly unfair" treatment.

House Ways and Means Committee Chairman Kevin Brady, R-Texas, responded with a promise to do more: “Senator — I strongly agree we should continue to improve the pass-through provisions at every step. You are a great champion for this." Congress is not subject to the Freedom of Information Act, but Treasury officials were copied on the email exchange. ProPublica obtained the exchange after suing the Treasury Department.

Kellner got his wish. In the final days of the legislative process, real estate investors were given a side door to access the full deduction. Language was added to the final legislation that allowed them to qualify if they had a large portfolio of buildings, even if they had small payrolls.

With that, some of the richest real estate developers in the country were welcomed into the fold.

The tax records obtained by ProPublica show that one of the top real estate industry winners was Donald Bren, sole owner of the Southern California-based Irvine Company and one of the wealthiest developers in the United States.

In 2018 alone, Bren personally enjoyed a deduction of $22 million because of the tax break. Bren's representatives did not respond to emails and calls from ProPublica.

His company had hired Wes Coulam, a prominent Washington lobbyist with Ernst & Young, to advocate for its interests as the bill was being hammered out. Before Coulam became a lobbyist, he worked on Capitol Hill as a tax policy adviser for Utah Sen. Orrin Hatch.

Hatch, then the Republican chair of the Senate Finance Committee, publicly took credit for the final draft of the new deduction, amid questions about the real estate carveout. Hatch's representatives did not respond to questions from ProPublica about how the carveout was added.

ProPublica's records show that other big real estate winners include Adam Portnoy, head of commercial real estate giant the RMR Group, who got a $14 million deduction in 2018. Donald Sterling, the real estate developer and disgraced former owner of the Los Angeles Clippers, won an $11 million deduction. Representatives for Portnoy and Sterling did not respond to questions from ProPublica.

Another gift to the real estate industry in the bill was a tax deduction of up to 20% on dividends from real estate investment trusts, more commonly known as REITs. These companies are essentially bundles of various real estate assets, which investors can buy chunks of. REITs make money by collecting rent from tenants and interest from loans used to finance real estate deals.

The tax cut for these investment vehicles was pushed by both the Real Estate Roundtable, a trade group for the entire industry, and the National Association of Real Estate Investment Trusts. The latter, a trade group specifically for REITs, spent more than $5 million lobbying in Washington the year the tax bill was drafted, more than it had in any year in its history.

Steven Roth, the founder of Vornado Realty Trust, a prominent REIT, is a regular donor to both groups' political committees.

Roth had close ties to the Trump administration, including advising on infrastructure and doing business with Jared Kushner's family. He became one of the biggest winners from the REIT provision in the Trump tax law.

Roth earned more than $27 million in REIT dividends in the two years after the bill passed, potentially allowing him a tax deduction of about $5 million, tax records show. Roth did not respond to requests for comment, and his representatives did not accept questions from ProPublica on his behalf.

Another carveout benefited investors of publicly traded pipeline businesses. Sen. John Cornyn, a Texas Republican, added an amendment for them to the Senate version of the bill just before it was voted on.

Without his amendment, investors who made under a certain income would have received the deduction anyway, experts told ProPublica. But for higher-income investors, a slate of restrictions kicked in. In order to qualify, they would have needed the businesses they're invested in to pay out significant wages, and these oil and gas businesses, like real estate developers, typically do not.

Cornyn's amendment cleared the way.

The trade group for these companies and one of its top members, Enterprise Products Partners, a Houston-based natural gas and crude oil pipeline company, had both lobbied on the bill. Enterprise was founded by Dan Duncan, who died in 2010.

The Trump tax bill delivered a win to Duncan's heirs. ProPublica's data shows his four children, who own stakes in the company, together claimed more than $150 million in deductions in 2018 alone. The tax provision for “small businesses" had delivered a windfall to the family Forbes ranked as the 11th richest in the country.

In a statement, an Enterprise spokesperson wrote: “The Duncan family abides by all applicable tax laws and will not comment on individual tax returns, which are a private matter." Cornyn's office did not respond to questions about the senator's amendment.

The tax break is due to expire after 2025, and a gulf has opened in Congress about the future of the provision.

In July, Senate Finance Chair Ron Wyden, D-Ore., proposed legislation that would end the tax cut early for the ultrawealthy. In fact, anyone making over $500,000 per year would no longer get the deduction. But it would be extended to the business owners below that threshold who are currently excluded because of their industry. The bill would “make the policy more fair and less complex for middle-class business owners, while also raising billions for priorities like child care, education, and health care," Wyden said in a statement.

Meanwhile, dozens of trade groups, including the Chamber of Commerce, are pushing to make the pass-through tax cut permanent. This year, a bipartisan bill called the Main Street Tax Certainty Act was introduced in both houses of Congress to do just that.

One of the bill's sponsors, Rep. Henry Cuellar, D-Texas, pitched the legislation this way: “I am committed to delivering critical relief for our nation's small businesses and the communities they serve."

Campaign to rein in mega IRA tax shelters gains steam in Congress

ProPublica is a Pulitzer Prize-winning investigative newsroom. Sign up for The Big Story newsletter to receive stories like this one in your inbox.

Series: The Secret IRS Files

Inside the Tax Records of the .001%

Two members of Congress who have long been responsible for shaping federal laws on retirement savings are considering major reforms after ProPublica exposed how the ultrawealthy are turning retirement accounts into gargantuan tax shelters.

Rep. Richard Neal, the Massachusetts Democrat who chairs the powerful House Ways and Means Committee, told ProPublica that he has directed the committee to draft a bill that “will stop IRAs from being exploited."

The committee is considering “limiting the total amount of money that can be saved in tax-preferred retirement accounts," Neal said in a written statement.

“Incentives in our tax code that help Americans save for retirement were never intended to enable a tax shelter for the ultra-wealthy," Neal said. “We must shut down these practices."

In addition, Sen. Ben Cardin, a Maryland Democrat who has co-authored a series of changes to retirement savings laws in the past decade, is also in favor of reforms that his spokesperson said would “prevent the type of massive abuses exemplified by the ultra-wealthy."

But provisions lurking deep in unrelated legislation currently wending its way through Congress could undermine those efforts.

In its June 24 story, ProPublica detailed that one technique investors have used to sock hundreds of millions of dollars — even billions — away in their IRAs is to fill the accounts with bargain-basement shares in companies that are not publicly traded, so they have no clear valuation. Then, when the companies go public or are sold, their accounts explode in value — with all of the gains tax-free.

Cardin's spokesperson told ProPublica that the senator now supports banning such transactions, which would be one of the biggest reforms in decades to the rules governing the accounts. The Internal Revenue Service recommended a similar change more than a decade ago. Congressional investigators wrote that an IRS team in 2009 had suggested “limiting the types of investments IRAs can make to publicly traded or otherwise marketable securities with a readily ascertainable fair market value."

Cardin is “considering reforms, such as banning the use of IRAs to purchase nonpublic investments," calling it “a good starting point while protecting IRAs for every day Americans to save for their retirement," his spokesperson wrote in an email.

The growing interest in changing the system gives momentum to the plans of Oregon Sen. Ron Wyden, chair of the Senate Finance Committee, who last month declared that he was eyeing a similar crackdown on giant IRAs.

Wyden's move came after ProPublica detailed how the Roth IRA, a ho-hum retirement account designed to help the middle class save for retirement, had been hijacked by the ultrawealthy, who used it to create gigantic onshore tax shelters. Tax records obtained by ProPublica revealed that Peter Thiel, a co-founder of PayPal and an early investor in Facebook, had a Roth IRA worth $5 billion as of 2019. As long as Thiel waits until he is six months shy of his 60th birthday, he will be able to withdraw his fortune tax-free.

Thiel made an end run around the strict limit on what can be put into a Roth IRA by purchasing so-called founders' shares of PayPal in 1999 when he was chairman and CEO of that company, according to tax records and a financial statement Thiel included in his application for citizenship in New Zealand. Securities and Exchange Commission records show Thiel bought 1.7 million shares for $1,700 — a price of a tenth of a penny per share. PayPal later told the SEC that the shares were among those sold at “below fair value."

When PayPal took off and Thiel's shares ballooned in value, he sold them and used the proceeds — still within his Roth — to invest in other startups, including Facebook, long before they went public, according to court records and Thiel's financial statement filed in New Zealand. He never had to make another contribution to his Roth again. The account's stratospheric growth all stemmed from a private stock deal available only to a handful of people.

This is the type of nonpublic IRA investment that Cardin is considering banning. A spokesperson for Thiel did not respond to requests for comment.

But this new appetite for reining in the accounts may be too late to slow contrary bipartisan legislation already rolling through Congress. Buried deep inside two complex and sweeping bills — each more than 140 pages long — are provisions that could make it harder for the IRS to crack down on the ultrawealthy who dodge tax rules.

Those bills, paradoxically, are co-sponsored by Cardin and Neal, two of the lawmakers who are now calling for reining in giant retirement accounts.

The House and Senate bills were introduced before ProPublica launched its ongoing series last month exposing how the country's richest citizens sidestep the nation's income tax system. ProPublica has obtained IRS tax return data on thousands of the wealthiest people in the U.S., covering more than 15 years, allowing it to conduct an unprecedented examination of how the ultrawealthy employ tricks to avoid taxes in ways that most Americans cannot.

The bills are being pitched as helping ordinary Americans save for retirement, including automatic enrollment of workers in employer-sponsored retirement plans. But they also include perks for retirement and financial industries, such as relaxing certain rules in ways that are seen as a boon for insurers.

Deciphering the handouts is nearly impossible without a background in the intricacies of retirement plan tax laws and the help of experts. The bills hide critical changes in language most laypeople would never understand. For instance, a key piece of the Senate bill reads, “Paragraph (2) of subsection (e) of section 408 is repealed." But the scope of that change only makes sense when layered with this: “Section 4975(c)(3) is amended by striking 'the account ceases to be an individual retirement account by reason of the application of section 408(e)(2)(A) or if'."

ProPublica had to reverse-engineer the meaning of that series of numbers and letters to determine that it would take away one of the most potent weapons in the IRS' arsenal: the ability to strip an entire IRA of its tax-favored status.

Complicated IRS and Department of Labor rules prohibit IRA investments that involve conflicts of interest or self-dealing. That can be a particular concern with nontraditional IRA investments, such as purchases of real estate or of shares of companies that are not publicly traded. Under the current law, if the IRS determines that a retirement account has engaged in a prohibited transaction, the agency can blow up the entire account — an event that Warren Baker, a tax attorney whose practice focuses on IRAs, likens to “Armageddon." The whole account then ceases to be an IRA, and the owner has to pay income taxes on it.

The two bills propose defusing that bomb. In the House bill, the tax benefits would only be stripped from the part of the account involved in the forbidden transaction. The Senate bill would loosen the rules even more, applying a 15% excise tax on the part of the account involved in the prohibited transaction without blowing up the account. A spokesperson for Cardin said, “The penalty jumps to 100% if not corrected in a timely manner."

Still, someone who violates the rules suddenly would have a “massive long-term upside benefit" of tax-free growth, Baker said, while “your downside risk is a penalty that is smaller than the capital gains rates," the federal tax on the income that's generated when stocks or other assets are sold.

Bob Lord, a tax attorney and tax counsel to Americans for Tax Fairness, said he has represented clients who settled Roth IRA cases because the threat of losing the tax benefits of their entire accounts was “leverage the IRS had." He was stunned when he read the bills and saw that power stripped from the IRS.

“These changes will lead to more aggressive transactions that lodge greater wealth in Roth IRAs, with less risk if the IRS audits," Lord said.

The proposed Senate bill, experts say, makes another concession to IRA owners who might be tempted to dodge the rules. Under current law, an IRA account holder who violates rules is never totally in the clear. That's because the current statute of limitations for violations is a bit of a gray area, experts say. The IRS, “could virtually go back indefinitely," said Jeffrey Levine, a CPA and chief planning officer at Buckingham Wealth Partners.

The Senate bill proposes stopping the clock at three years. Yet, it can take more than three years for some nontraditional investments to balloon. If the IRS were to discover something amiss, under the bill's proposed statute of limitations it would be too late to act.

“For the little guy this makes all the sense in the world," Levine said. But for the ultrawealthy with huge accounts and squadrons of lawyers, he said, the changes could incentivize bad behavior. “Someone with all the resources in the world could say, 'I'll do this now that my risk-reward calculation is different and I'm looking at getting through three years and then I'm kind of home free.' That, you know, is a real boon for those who want to take advantage of the system."

The House bill is co-sponsored by Neal and Rep. Kevin Brady, a Texas Republican, and the Senate bill is co-sponsored by Cardin and Sen. Rob Portman, an Ohio Republican.

A spokesperson for Portman defended the legislation, which she said was “borne out of contact from our constituents — including innocent middle class savers who had their retirements wrecked by innocent and minor errors." ProPublica asked aides to Portman and Cardin for examples, but neither provided any. A Cardin spokesperson wrote in an email that “there usually is not litigation when this happens, and non-public examples are confidential taxpayer information."

In a joint statement, the offices of Portman and Cardin defended the Senate bill, saying it would help small businesses offer 401(k) retirement plans, expand access to savings for low-income Americans and “allow people who have saved too little to set more aside for retirement." The new legislation, they added, included measures to prevent Americans from inadvertently losing their IRAs while “implementing safeguards to prevent abuse."

Brady's communications director asked for questions in writing, then did not respond.

A staffer with Neal's Ways and Means Committee said the House bill had broad support and touted many provisions, including the automatic enrollment of employees in retirement plans, a national lost-and-found to locate retirement plans from prior jobs and a requirement that employers let certain long-term, part-time workers enroll in 401(k) plans.

The House bill, she noted, doesn't repeal the prohibited transaction rules; it limits the impact to the inappropriate purchase. She described Neal as “very committed to maintaining these important rules and believes that full sanctions should apply when violated."

Here's how to file your state and federal taxes for free in 2021

by Kristen Doerer for ProPublica, Justin Elliott and Karim Doumar

ProPublica is a Pulitzer Prize-winning investigative newsroom. Sign up for The Big Story newsletter to receive stories like this one in your inbox.

Series: The ProPublica Free Tax Guide

Free, Fact-Checked Tax Information. That's All.

Most Americans are eligible for free tax-preparation services, but the truly free options can be hard to find. If you're not careful, you could end up using a service that says it's free but demands payment after you've spent time entering your information.

Now that the IRS haspushedthe deadline for 2020 taxes to May 17, you have even more time to make sure you're using the service that's right for you.

How do you file online for free?

If you make less than$72,000 a year, you can find free tax filing options at the IRS Free File webpage.

Here are Free File options from TurboTax, TaxSlayer and others. (H&R Block has left the Free File program since last year.)

Each site has its own eligibility requirements, so be sure to find one that will be free for you.

It can take a bit of effort to find an option that fits your situation. Try using the IRSlookuptoolto find the right one. Most of the options provide tax prep for both federal and state returns.

Best for: People who make less than the income cap and want a convenient and easy way to file online.

If you make more than $72,000 a year, you may have access to free options offered by several commercial tax prep companies, like Intuit (TurboTax), H&R Block or TaxAct.

But buyer beware: Some companies use a variety of tactics to try to wring money out of you, often only throwing up a paywall after you've gone through the trouble of inputting most of your information.

The widely advertised “free" options are typically only really free based on which tax forms you need to file. Which forms are free and which will trigger a demand for a fee depends on the company. So read the fine print before you decide.

  • Here is the list of forms supported by H&R Block's “free online" version.
  • Here is the list of forms supported by TaxAct's “free" offer. Click the tab labeled “forms."
  • Here is the list of forms supported by TurboTax “Free Edition."

Credit Karma also offers a free tax filing service for “all supported forms," but the company tries to monetize your personal tax data by using it to target you with advertising.

Best for: People who don't qualify for Free File but have income only from a standard job and perhaps a bank account, and who want to file online.

If you're in the military, you can use MilTax, a service provided by the Department of Defense that uses a version of H&R Block's tax software. It is available for free to active-duty service members as well as those in the National Guard or the reserves, as well as their families. There are no income or tax form restrictions. There are also free, in-person options to get tax help if you are in the military or family — see the section below.

You can also get free advice from a professional who understands tax issues specific to the military. The phone number is 800-342-9647, or you can live chat with them.

Best for: People in the military, guard or reserves and their families.

How can I get personal tax help for free?

You can qualify for the IRS'Volunteer Income Tax Assistance (VITA) program if you:

  • Make less than around $57,000 a year, OR
  • Live with a disability, OR
  • Speak limited English.

You can qualify for the IRS'Tax Counseling for the Elderly program if you:

  • Are at least 60 years old.

These programs match you with IRS-certified volunteers across the country who can help with free basic income tax preparation and electronic filing. You can use the Volunteer Income Tax Assistance locator tool or call 800-906-9887 to find someone to help you. Keep in mind that some locations may require an appointment.

Best for: People who are confused by the tax process and want someone to help walk them through the process.

If you're in the military and want individual tax help, you can get freein-person tax help on many U.S. military bases worldwide. Military.com's base guide is a good place to start.

Best for: People in the military and their families who want advice from someone who knows the ins and outs of military tax filing.

Why is TurboTax charging me?

If you make less than $39,000 a year (or $72,000 if you're in the military) and TurboTax is telling you it costs money to file, you are probably using the wrong version of TurboTax. Don't worry, there is a way to access the truly free version.

As ProPublica reported in 2019, TurboTax purposely hid its Free File product and directed taxpayers to a version where many had to pay, called the TurboTax Free Edition. If you clicked on this “FREE Guaranteed" option, you could input a lot of your information, only to be told toward the end of the process that you need to pay.

You can still accessTurboTax's Free File version. This version is offered through the Free File agreement.

TurboTax's misleadingadvertisingandwebsite designdirected users to more expensive versions of the software, even if they qualified to file for free. After our stories published, some people demanded and got refunds. Intuit, the maker of TurboTax, faces several investigations and lawsuits over this practice. The company has denied wrongdoing, and has moved to acquire other free tax-preparation companies like Credit Karma.

Following ProPublica's reporting, the IRS announced an update to its agreement with the tax-preparation companies. Among other things, the update bars the companies from hiding their Free File offerings from Google search results. It also makes it so each company has to name their Free File service the same way, using the format: IRS Free File Program delivered by [COMPANY NAME].

What's the difference between TurboTax's “Free Guaranteed" and IRS Free File Delivered by TurboTax?

TurboTax Free Edition is not always free. It has only been free for tax returns that the company defines as “simple." That often means people with student loans and freelance income actually have to pay to file. Look for Intuit's “IRS Free File Program delivered by TurboTax." This year, you are eligible if you:

  • Make less than $39,000 a year, OR
  • Make less than $72,000 a year and serve in the military.

What is Free File, and who is the Free File Alliance?

The Free File Alliance is actually a group of tax companies that — contrary to the name — is in the business of charging people to help them file their taxes. They spent a lot of money to make sure that the IRS didn't develop its own free tax filing service that would compete with what they have to offer. As part of the new Free File Alliance deal, the IRS is now able to offer a competing service, but it's not doing so this year.

The Free File Alliance companies have agreed to offer free tax filing for a certain percentage of the population based on income. Head to the IRS website to see which option is the best for you. These are the companies in the alliance:

  • 1040NOW Corp.
  • ezTaxReturn.com
  • FileYourTaxes
  • Free Tax Returns
  • Intuit
  • OnLine Taxes
  • TaxACT
  • TaxHawk
  • TaxSlayer

About this guide:

ProPublica has reported extensively about taxes, the IRS Free File program and the IRS. Specifically, we've covered the ways in which the for-profit tax preparation industry — companies like Intuit (TurboTax), H&R Block and Tax Slayer — has lobbied for the Free File program, then systematicallyundermined it with evasive search tactics and confusing design. These companies also work to fill search engine results with tax “guides" that sometimes route users to paid products. This guide is not personalized tax advice, and you should speak to a tax professional about your specific tax situation.

Susan Collins backed down from a fight with private equity. Now they’re underwriting her reelection

ProPublica is a Pulitzer Prize-winning investigative newsroom. Sign up for The Big Story newsletter to receive stories like this one in your inbox.

In late November 2017, Senate Republicans were racing to secure the votes for their sweeping tax overhaul. With no Democrats supporting the bill and even some Republicans wavering, Sen. Susan Collins, the Maine Republican, found herself with enormous leverage.

The day before the vote, she offered an amendment to make the legislation, which lavished tax cuts on corporations and the wealthy, more equitable. It expanded a tax credit to make child care more affordable. To pay for it, she took aim at a tax break cherished by the private equity industry.

Then Collins backed down. The day after she introduced it, as the Senate voted on the bill, a Republican Senate aide told a Treasury Department official that Collins was “no longer offering her amendment," according to emails obtained by ProPublica through a Freedom of Information Act lawsuit. Her retreat was a significant victory for Senate Majority Leader Mitch McConnell. Collins put aside her opposition and voted for the bill, which passed 51-49.

Her turnabout has been one of the mysteries surrounding the $1.5 trillion tax bill, which slashed the corporate rate. The new emails and interviews shed light on how quickly Collins climbed down from her amendment proposal and how the industry maneuvered to preserve the break in the new law, which remains President Donald Trump's most important legislative achievement.

Nearly three years later, Collins is facing a tough reelection battle and the private equity industry has become her most reliable source of donations. She has gotten more than half a million dollars in campaign contributions from the private equity industry this cycle, more than any other senator, according to the Center for Responsive Politics, which tracks political donations.

What's more, Steve Schwarzman, the billionaire chairman and chief executive of the private equity giant Blackstone, has given $2 million to a super PAC backing her. (Schwarzman, a major Republican donor, has also given $20 million to a super PAC supporting Collins and other Republican Senate candidates.) The failure of Collins' amendment likely saved Schwarzman alone tens of millions of dollars in taxes, according to tax experts.

Annie Clark, a Collins campaign spokeswoman, said Collins secured other significant changes to the bill. The amendment cutting carried interest stood no chance because it would've required 60 votes to pass if the Senate had voted on it, she said.

“Given the opposition to the amendment at the time — not only from Republicans, but from Democrats as well — it would certainly have failed," Clark said in a statement.

A Schwarzman spokeswoman said in a statement, “Steve has long supported Senator Collins because of her independence, hard work and integrity. He does not closely follow all of her specific policy positions."

The carried interest loophole, as its critics, including Collins, have called it, has long been the target of reform efforts.

The tax break is especially lucrative for the private equity industry, which invests in non-public businesses. A major way that executives at private equity firms like Blackstone make money is by taking a share of profits when the companies they invest in are sold.

The debate over carried interest centers on how this money should be taxed: as an investment return for private equity executives or a bonus that the firm's clients pay for good performance. Today, it's treated like an investment and taxed at a lower capital gains rate. If it were counted as a bonus, it would be taxed like part of the executives' salaries, at the higher ordinary income tax rate. That discount — currently around 20 percentage points — in what Wall Street executives owe to the government quickly adds up to tens of billions of dollars.

When Trump became president and Republicans started pursuing an overhaul of the tax code, private equity had reason to be worried. The party had a long wish list of tax cuts but a limited number of ways to pay for them without increasing the deficit by more than Senate rules allowed, $1.5 trillion over 10 years. Eliminating carried interest, as Trump had proposed, was one of them.

And the tax break had faced years of opposition. The Obama administration made an ultimately unsuccessful attempt to raise the carried interest tax rate, an effort that Schwarzman famously compared to the Nazis invading Poland. (He later apologized for the analogy.)

Trump himself repeatedly complained about carried interest during his presidential campaign. “These are guys that shift paper around and they get lucky," he said in 2015. “They are paper-pushers. They make a fortune. They pay no tax. It's ridiculous, OK?"

To blunt the effort, the American Investment Council, the industry's Washington trade group, proposed a concession it hoped would mollify lawmakers who might consider killing the loophole. AIC pitched House Republicans on modestly extending the amount of time that hedge funds, private equity firms and others must hold onto investments to qualify for the tax break, according to three people familiar with the matter.

That's exactly what happened. Rep. Kevin Brady, R-Texas, the chairman of the House Ways and Means Committee, proposed tweaking carried interest rather than eliminating it. The holding period would change from one year to three years — a change that tax experts say does little to close the loophole.

“It's laughable. Almost nobody will end up paying any additional tax. Tax planners have a million ways to Sunday to try to avoid it, some more legitimate than others, and the IRS is notoriously inept at auditing these types of issues," said Gregg Polsky, a former corporate tax lawyer who is now a professor at University of Georgia law school.

But the loophole still faced a threat. AIC had identified Collins as a senator who might come after carried interest, according to two people familiar with the matter, and on Nov. 30, Collins spoke on the Senate floor to pitch a handful of amendments to the bill.

One priority, she said, was to alleviate the burden on poor families of the costs of care for children or elderly relatives. And to raise money for this new government subsidy, she would roll back Wall Street's carried interest tax break.

“These are the lowest income families who need help the most in paying for child care or care for a dependent, elderly parent or grandparent or other relative; yet virtually none of them qualify for the credit," Collins said. “To pay for making the child and adult dependent care credit refundable, my amendment would close the carried interest loophole, a tax reform that the president has endorsed."

Collins' staff had reached out to academics who specialize in the arcane details of carried interest to help them craft the legislative language, according to one Senate tax aide. She settled on upping the holding period from three years, as Brady has proposed, to eight — which, experts say, would have significantly eroded the tax break's value.

As the Senate was moving toward passing the bill the day after Collins pitched her amendment, Drew Maloney, the Treasury Department's assistant secretary for legislative affairs, emailed the chief of staff to Sen. Rob Portman, R-Ohio, asking what had “happened with carried interest."

“Collins no longer offering her amendment," replied Portman's chief of staff, Mark Isakowitz.

Collins “[c]ame up with a different pay for to fund her medical expense deduction so she isn't offering it any more," Isakowitz continued.

It's unclear exactly what Isakowitz meant; he appears to have conflated Collins' amendment to expand the child and dependent tax credit — for which closing the carried interest loophole was a “pay for," Washington jargon for a revenue-generating measure that offsets a tax cut — with another amendment she proposed retaining a tax deduction for medical expenses and lowering the income threshold necessary to claim it.

Maloney declined to comment. So did Isakowitz, who now runs Google's Washington office.

It's not clear exactly why Collins dropped her last-minute, long-shot attempt to kill carried interest. Three other amendments that Collins introduced on the same day made it into the bill, including an expansion of the medical expense tax deduction and preserving taxpayers' ability to deduct up to $10,000 in state and local income taxes from their federal tax returns.

Clark, Collins' spokeswoman, said the senator continues to support closing the carried interest loophole to pay for an expansion of the child and dependent care tax credit, but the lack of support for it at the time meant the amendment “had absolutely no chance" of making it into the bill.

“Any claim that Senator Collins didn't pursue this amendment because of any lobbying effort is completely false," she said. “Anyone who knows her knows that she always does what she thinks is right. Any insinuation to the contrary is false — and an insult to her integrity."

Maloney, who, internal Treasury emails show, kept close tabs on the carried interest issue throughout 2017, left the administration six months after the tax overhaul passed to take a job running the American Investment Council, the private equity trade group. He later hired Brad Bailey, another top Treasury Department official, to work as one of the trade group's lobbyists.

Another Treasury Department official, Jared Sawyer, has lobbied for AIC since leaving the administration to take a job at a lobbying firm. And Eli Miller, the chief of staff to Treasury Secretary Steve Mnuchin, who was deeply involved in the tax overhaul, left government last year to become a government relations executive at Blackstone.

While Collins' Democratic opponent, Sara Gideon, has outraised Collins' campaign, Wall Street billionaires have stepped up to boost the pro-Collins 1820 PAC, which can accept unlimited donations and has spentheavily on TV and other ads. Schwarzman is the group's single-largest donor. Behind him is Ken Griffin of Chicago hedge fund giant Citadel, who has chipped in $1.5 million.

Citadel's lobbying disclosures show the firm lobbied Congress on the carried interest issue in 2017, as well as the broader tax bill. A Citadel spokesman pointed to Griffin's comments several years ago on carried interest.

“Almost all the income that we generate is short term in nature," Griffin said in 2013. “So my tax rate is pretty much the highest federal marginal rate. So I don't have a lot of skin in the game on this issue from my personal vantage point but I have an interest in this as a matter of principle."

Griffin then said he believed the current favorable tax treatment of carried interest should be maintained.

Gideon has no similar outside group supporting her and her campaign has received $242,000 in donations from people who work in private equity, according to the Center for Responsive Politics. A narrow favorite in the race, Gideon has attacked Collins for her support of the tax overhaul.

In December 2017, when it became clear that, despite the president's promises, the tax bill would not meaningfully address carried interest, Axios' Mike Allen asked Gary Cohn, the director of Trump's National Economic Council, what he would change about the bill if he could change one thing.

“We would've cut carried interest," he replied. “We hit opposition in that big white building with the dome at the other end of Pennsylvania Avenue every time we tried."

When Allen pressed Cohn to explain what had happened, he alluded to the power that hedge funds, private equity and venture capital wield in Washington. “Look, the reality of this town is that constituency has a very large presence in the House and the Senate, and they have really strong relationships on both sides of the aisle," he said.

Now the industry is preparing to fight the same battle again. Joe Biden has proposed raising capital gains taxes for those who make at least $1 million a year to equal the income tax rate, effectively eliminating the carried interest loophole for the richest Americans.

Biden's plan to kill carried interest does not appear to have dented his support from private equity.

Jon Gray, Blackstone's president, hosted a fundraiser for Biden in July and introduced him at another one earlier this year. Tony James, another top Blackstone executive, hosted one in June. (Gray and James have also given a combined $2.25 million to the Senate Majority PAC, which supports Democratic Senate candidates including Gideon.) And Alex Katz, a former aide to Senate Minority Leader Chuck Schumer who now works in government relations for Blackstone, is raising money for Biden's transition effort.

The Biden campaign declined to comment.

The Justice Department unleashes prosecutors to potentially intervene in the election

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The Department of Justice has weakened its long-standing prohibition against interfering in elections, according to two department officials.

Avoiding election interference is the overarching principle of DOJ policy on voting-related crimes. In place since at least 1980, the policy generally bars prosecutors not only from making any announcement about ongoing investigations close to an election but also from taking public steps — such as an arrest or a raid — before a vote is finalized because the publicity could tip the balance of a race.

But according to an email sent Friday by an official in the Public Integrity Section in Washington, now if a U.S. attorney's office suspects election fraud that involves postal workers or military employees, federal investigators will be allowed to take public investigative steps before the polls close, even if those actions risk affecting the outcome of the election.

The email announced “an exception to the general non-interference with elections policy." The new exemption, the email stated, applied to instances in which “the integrity of any component of the federal government is implicated by election offenses within the scope of the policy including but not limited to misconduct by federal officials or employees administering an aspect of the voting process through the United States Postal Service, the Department of Defense or any other federal department or agency."

Specifically citing postal workers and military employees is noteworthy, former DOJ officials said. But the exception is written so broadly that it could cover other types of investigations as well, they said.

Both groups have been falsely singled out, in different ways, by President Donald Trump and his campaign for being involved in voter fraud. Trump has repeatedly attempted to delegitimize ballots sent through the postal service, just as the country experiences increased voting by mail spurred by the coronavirus pandemic. He has also raised the specter that the ballots of military members, among whom he enjoys broad support, might be suppressed.

The DOJ and the White House did not immediately respond to requests for comment.

Experts who reviewed the revision said they were concerned it could be exploited to help the DOJ bolster Trump's campaign.

“It's unusual that they're carving out this exception," said Vanita Gupta, the former head of the DOJ Civil Rights Division under President Barack Obama. “It may be creating a predicate for the Justice Department to make inflated announcements about mail-in vote fraud and the like in the run-up to the election."

In a break from long-standing practice last month, a U.S. attorney in Pennsylvania publicly announced that the DOJ was investigating whether local elections officials illegally discarded nine mail-in military ballots. Attorney General William Barr personally briefed Trump on the case before it was publicly announced, The Washington Post reported. Trump later cited it as an example to support his claims of widespread mail-in voter fraud, a false assertion Barr has has helped amplify. It's not clear where the federal probe stands, but Pennsylvania's top elections official said early indications point to an error, not fraud.

The new policy carveout, Gupta said, could be designed to both justify the widely criticized Pennsylvania announcement and open the door for more such moves in the coming weeks.

Justin Levitt, a former deputy assistant attorney general in the DOJ's civil rights division, also expressed concern that the department could be encouraging prosecutors to make more public announcements about incomplete investigations, as they did in the Pennsylvania case.

“It alarms me that the DOJ would want to authorize more of the same in and around the election," he said. “It's incredibly painful for me to say, but given what we've seen recently, Americans shouldn't trust DOJ announcements right now."

The Friday email was sent to a group of dozens of prosecutors around the country known as district election officers. They monitor election procedures and take complaints on Election Day from the public about alleged crimes and serve as the federal points of contact for local election officials.

For decades, the work of federal prosecutors has been guided by a strict policy of non-interference in elections.

A 281-page document titled “Federal Prosecution of Election Offenses" is the handbook for district election officers. The latest edition, from 2017, warns against launching public investigations, without approval granted for extraordinary cases, into alleged fraud before an election is over.

Such a step, the handbook says, “runs the obvious risk of chilling legitimate voting and campaign activities. It also runs the significant risk of interjecting the investigation itself as an issue, both in the campaign and in the adjudication of any ensuing election contest."

One current DOJ official told ProPublica that prosecutors have historically been warned not to allow themselves to be dragged into candidate disputes. “That's what they drill into us: the policy of non-interference and never, ever, ever announce an investigation," the official said.

The Justice Department may have violated Attorney General Barr’s own policy memo

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When the Justice Department recently publicized an ongoing investigation into potentially improperly discarded Trump ballots, critics accused it of violating long-standing agency policy against interfering in an election.

But the unusual decision to publicly detail the Pennsylvania case may also have run afoul of guidelines that Attorney General William Barr himself issued to federal prosecutors this year, according to a memo obtained by ProPublica.

In May, Barr wrote a directive to all Justice Department employees imploring them to be “particularly sensitive to safeguarding the Department's reputation for fairness, neutrality, and non-partisanship" when it comes to election-related crimes.

“Partisan politics," he wrote, “must play no role in the decisions of federal investigators or prosecutors regarding any investigations or criminal charges. Law enforcement officers and prosecutors may never select the timing of public statements (attributed or not), investigative steps, criminal charges, or any other action in any matter or case for the purpose of affecting any election, or for the purpose of giving an advantage or disadvantage to any candidate or political party."

Nevertheless, last month Barr's Justice Department issued a press release announcing an investigation into whether local elections officials illegally discarded nine mail-in military ballots in Pennsylvania. The announcement of an open investigation was highly unusual. Even more abnormal was that the press release specified that at least seven of those ballots were for President Donald Trump.

While the motivation of the Pennsylvania press release is unclear, Barr had personally briefed Trump on the matter before the announcement, The Washington Post subsequently reported, citing an anonymous source. The president raised it in a media interview and then DOJ's Pennsylvania office announced the investigation.

Then, the Trump campaign quickly jumped on the Pennsylvania case to bolster those claims.

“BREAKING: FBI finds military mail-in ballots discarded in Pennsylvania. 100% of them were cast for President Trump. Democrats are trying to steal the election," a campaign official tweeted.

Justin Levitt, a former deputy assistant attorney general in the DOJ's civil rights division, said the Pennsylvania press release was “flatly inconsistent" with Barr's memo “and shamefully so."

“There's absolutely no legitimate law enforcement reason I know of to mention who the ballots were cast for: They were either dealt with properly or not properly," he said. “And if there's no good reason, it leaves only the most likely bad reason: that the identity of the candidate was revealed for partisan political purposes."

Some experts did not agree . Samuel Buell, a former federal prosecutor who is now a professor at Duke Law School, said Barr could argue that “any public announcement about a ballot investigation complies with [the memo] because the language is so broad."

Barr, he said, could say the “purpose" of the Pennsylvania announcement was not to affect the outcome of the election or support a particular candidate, but some other non-prohibited motivation like “protecting the vote."

The Barr memo closelymirrored election-year guidance that previous attorneys general sent out under both the Obama and George W. Bush administrations. Barr himself said at his Senate confirmation hearings last year that the election policies were in place because the incumbent party has “their hands on the levers of the law enforcement apparatus of the country, and you do not want it used against the opposing political party."

Asked whether the Pennsylvania announcement ran afoul of the agency's election policies, Justice Department spokeswoman Kerri Kupec responded: “No." She declined to elaborate.

The U.S. attorney overseeing the case is David Freed, a former Republican nominee for Pennsylvania state attorney general who was nominated for his current role by Trump in 2017. In a publicly released letter, Freed said he was detailing initial findings despite an ongoing investigation “based on the limited amount of time before the general election and the vital public importance of these issues."

A second memo obtained by ProPublica, issued in August by Corey Amundson, chief of the DOJ's Public Integrity Section, was even more explicit.

In it, Amundson reiterated the Justice Department's long-standing policy in election fraud cases: “Overt criminal investigative measures should not ordinarily be taken in matters involving alleged fraud in the manner in which votes were cast or counted until the election in question has been concluded."

The memo was addressed to the Attorney General Advisory Committee, a group of U.S. attorneys that advise the attorney general.

The policy Amundson cites appears to make an exception for extraordinary cases. But it seems unlikely that would apply to the case in Pennsylvania. That involved only nine ballots, which appear to have been discarded by a sole contract employee. The motivation may have been an innocuous attempt to follow Pennsylvania rules barring ballots sent back without the proper envelope.

Current and former Justice Department officials told ProPublica that, even without the memos from top agency officials including Barr, the Pennsylvania press release violated long-standing department policy. They explained that prosecutors not only should not announce that they are investigating, but that they should be slow even to start an election-sensitive investigation during the campaign. Such an investigation is so sensitive, an opposing candidate could use it to smear his or her opponent.

“That's what they drill into us: the policy of non-interference and never, ever, ever announcing an investigation," one official said. “That's why the thing in Pennsylvania is bonkers, completely bonkers."

A spokeswoman for Freed declined to comment.

Barr has amplified Trump's attempt to discredit mail-in voting before, claiming falsely that there is widespread fraud.

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This story was co-published with The Military Times.

In patriotism-drenched promotions, press releases and tweets, TurboTax promotes special deals for military service members, promising to help them file their taxes online for free or at a discount.

Yet some service members who've filed by going to the TurboTax Military landing page told ProPublica they were charged as much as $150 — even though, under a deal with the government, service members making under $66,000 are supposed to be able to file on TurboTax for free.

Liz Zimmerman is a mother of two teenage daughters and a toddler who lives with her husband, a Navy chief petty officer, in Bettendorf, Iowa, just across the river from the Rock Island military facility. When Zimmerman went to do her taxes this year, she Googled “tax preparation military free” and, she recalled in an interview, TurboTax was the first link that popped up, promising “free military taxes.” She clicked and came to the site emblazoned with miniature American flags.

But when Zimmerman got to the end of the process, TurboTax charged her $60, even though the family makes under the $66,000 income threshold to file for free. “I’ve got a kid in braces and I’ve got a kid in preschool; $60 is half a week’s worth of groceries,” she said. “Who needs date night this month? At least I filed my taxes.”

In the commercial version of TurboTax that includes the “military discount,” customers are charged based on the tax forms they file. The Zimmermans used a form to claim a retirement savings credit that TurboTax required a paid upgrade to file. If they’d started from the TurboTax Free File landing page instead of the military page, they would have been able to file for free.

Like many other tax prep companies, Intuit, the maker of TurboTax, participates in the Free File program with the IRS, under which the industry offers most Americans free tax filing. In return, the IRS agrees not to create its own free filing system that would compete with the companies. But few of those who are eligible use the program, in part because the companies aggressively market paid versions, often misleading customers. We’ve documented how Intuit had deliberately made its Free File version difficult to find, including by hiding it from search engines.

In a statement, Intuit spokesman Rick Heineman said, “Intuit has long supported active-military and veterans, both in filing their taxes and in their communities, overseas, and in the Intuit workplace.” He added: “Intuit is proud to support active military, including the millions of men and women in uniform who have filed their tax returns completely free using TurboTax.”

To find TurboTax’s Free File landing page, service members typically have to go through the IRS website. TurboTax Military, by contrast, is promoted on the company’s home page and elsewhere. Starting through the Military landing page directs many users to paid products even when they are eligible to get the same service for no cost using the Free File edition.

An Intuit press release this year announced “TurboTax Offers Free Filing for Military E1- E5” — but refers users to TurboTax Military and does not mention the actual Free File option. (E1-E5 refers to military pay grades.) It was promoted on the company’s Twitter feed with a smiling picture of a woman wearing fatigues outside her suburban home. Google searches for “TurboTax military,” “TurboTax for soldiers” and “TurboTax for troops” all produce top results sending users to the TurboTax Military page.

That site offers a “military discount.” Some service members can use it to file for free, depending on their pay grade and tax situation. Others are informed — only after inputting their tax data — that they will have to pay.

In one instance, Petty Officer Laurell, a hospital corpsman in the Navy who didn’t want his full name used, was charged even though he makes under $66,000. TurboTax charged Laurell $95 this year and $100 last year, his receipts show.

“I am upset and troubled that TurboTax would intentionally mislead members of the military,” said Laurell, who has been in the service for a decade.

Using receipts, tax returns and other documentation, we verified the accounts from four service members who were charged by TurboTax even though they were eligible to use Free File. They include an Army second lieutenant, a Navy hospital corpsman and a Navy yeoman.

The New York regulator investigating TurboTax is also examining the military issue, according to a person familiar with the probe.

Active-duty members of the military get greater access to Free File products than other taxpayers. All Americans who make under $66,000 can use products offered by one of 12 participating companies in the program. But each company then imposes additional, sometimes confusing eligibility requirements based on income, age and location.

Those additional requirements are not imposed on service members for most of the Free File products.

TurboTax’s Free File edition, for example, is available to active-duty military and reservists who make under $66,000 in adjusted gross income compared with a threshold of $34,000 for everyone else.

It's unclear how many service members were charged by TurboTax, even though they could have filed for free. The company declined to respond to questions about this.

Jennifer Davis, government relations deputy director of the National Military Family Association, said the group is concerned by ProPublica’s findings about Americans being charged for tax services that should be free. “As an organization dedicated to improving the well-being of military families, we are concerned that many military families have fallen prey to these fraudulent actions as well,” she said. Davis pointed out that service members have a range of other free tax filing options, including in-person help on many bases and an online option through the Defense Department called MilTax.

We tested TurboTax Military and TurboTax Free File using the tax information of a Virginia-based Navy sailor and his graphic designer wife with a household income of $53,000.

The filing experiences had just one major difference: TurboTax Military tried to upgrade us or convince us to pay for side products six times. We declined those extras each time. Finally, the program told us we had to pay $159.98 to finish filing.

And that “military discount”? All of $5.

In the Free File version, by contrast, we were able to file completely free.

Here’s what happened when we landed on TurboTax Military:

The software took us through filing our taxes in the standard question-answer format used across all TurboTax products. We entered the sailor’s employer and income information.

Then TurboTax told us we were going to save some money because of our service.

“Congrats! You qualify for our Enlisted military discount.”

We were then repeatedly offered other paid products.

TurboTax recommended we purchase “+PLUS,” which promises “24/7 tax return access” and other services for $19.99.

We were offered “TurboTaxLive” — access to advice from a CPA — for $194.99.

We were also offered “MAX,” which includes audit defense and identity loss insurance for $59.99 (a good deal, the company suggests, because the products represent a “$125.00 value”).

We rejected all of these offers. We finished filing the sailor’s military income and added his wife’s 1099 income of $15,000 and her modest business expenses.

When we were done entering their information, the software broke some bad news: We would need to upgrade to TurboTax Self-Employed for $114.99 (minus $5 thanks to the military discount).

When we started on TurboTax Free File instead of TurboTax Military and entered the same information, the filing experience was virtually identical, with two major differences: We weren’t pitched side products such as audit defense and the final price was $0.

While the sailor’s family was eligible for Free File, TurboTax Military never directed us to the product, even after we entered a family income of less than $66,000.

On May 10, the New York Department of Financial Services sent a request for documents to USAA, the insurance company that caters to service members, according to a person familiar with the investigation. USAA promotes TurboTax Military, and DFS, which regulates insurance companies, sought records related to any deals with Intuit and other tax prep firms. Two other insurance companies, Progressive and AAA, also received requests for records from DFS. Spokespeople for the three companies didn’t respond to requests for comment.

TurboTax first launched the Military Edition in 2012. "TurboTax has a long history of supporting the military and many of our employees have served our country,” the then-head of TurboTax said in the company’s press release.

It has apparently been a lucrative business. On an earnings call six months later, Intuit’s then-CEO Brad Smith boasted “we saw double-digit growth this season from the military and digital native customer segments.”

“Given our scale and our data capabilities,” he said, “we plan to extend this advantage to even more taxpayers next season.” Smith is now executive chairman of Intuit’s board.

Last week, a class action was filed against Intuit by a law firm representing a Marine, Laura Nichols, who was charged by TurboTax even though she was eligible to file for free, according to the complaint. The suit cites ProPublica’s previous reporting on the issue. The company declined to comment.

Did you use TurboTax Military? Please tell us about your experience.

Have you worked for Intuit or another tax preparation company? We want to hear from you, too. Fill out our questionnaire or contact Justin at justin@propublica.org or via Signal at 774-826-6240.

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