Mike Spies

Top Trump campaign fundraiser played key role in planning the rally that preceded the siege: text messages

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In the week leading up to the Jan. 6 rally in Washington, D.C., that exploded into an attack on the Capitol, a top Trump campaign fundraiser issued a directive to a woman who had been overseeing planning for the event.

“Get the budget and vendors breakdown to me and Justin," Caroline Wren wrote to Cindy Chafian, a self-described “constitutional conservative," in a Dec. 28 text message obtained by ProPublica.

Wren was no ordinary event planner. She served as a deputy to Donald Trump Jr.'s girlfriend, Kimberly Guilfoyle, at Trump Victory, a joint presidential fundraising committee during the 2020 campaign. The Justin mentioned in her text was Justin Caporale, a former top aide to first lady Melania Trump, whose production company helped put on the event at the Ellipse.

Text messages and an event-planning memo obtained by ProPublica, along with an interview with Chafian, indicate that Wren, a Washington insider with a low public profile, played an extensive role in managing operations for the event. The records show that Wren oversaw logistics, budgeting, funding and messaging for the Jan. 6 rally that featured President Donald Trump.

Chafian told ProPublica that Wren and others had pushed her aside as plans intensified, including as a late effort was made to get Trump to speak at the event.

On Dec. 29, after receiving the budget, Wren instructed Chafian, via text, to hold off on printing event-related slogans “until we decide what the messaging is and we have no clue on timing because it all depends on the votes that day so we won't know timing for a few more days." The “timing" appears to be a reference to Congress' Jan. 6 vote to certify the election results.

Wren's services were enlisted by a major donor to Trump's presidential campaign, according to The Wall Street Journal, which reported Saturday that Julie Jenkins Fancelli, the heiress to Publix Super Markets, committed some $300,000 to fund the Jan. 6 rally.

The funding commitment by Fancelli, who Federal Election Commission records show has donated more than $1 million to Trump Victory, the president's campaign and the Republican National Committee since 2018, was facilitated by the right-wing conspiracy peddler Alex Jones, the Journal reported. Chafian told ProPublica that she herself had been directed by Jones to Wren, who, she was told, had ties to a wealthy donor who wanted to support the January affair. Chafian said the donor is a woman but wouldn't disclose her name, citing a confidentiality agreement.

Fancelli hasn't responded to messages left at numbers listed for her.

The Associated Press had previously reported that Wren was listed as a “VIP Advisor" in an attachment to a National Park Service permit for the Jan. 6 event issued to Women for America First, a pro-Trump nonprofit run by the mother-daughter duo Amy and Kylie Jane Kremer. Chafian had worked on and off with Women for America First since October 2019.

But that title gives little indication of the scope of Wren's role in managing the “March to Save America" event, where the president would tell thousands of supporters to walk to the Capitol and “demand that Congress do the right thing and only count the electors who have been lawfully slated," the records show.

A guidance memo provided to VIP attendees of the Jan. 6 rally further establishes Wren's centrality to the event. She is listed, along with three other people, as one of the primary points of contact for the demonstration. The Kremers, whose nonprofit was attached to the event, are not mentioned at all.

Wren hasn't responded to requests for comment about the role she played in organizing the Jan. 6 rally. In a statement to the Journal, she said her role in the event was to “assist many others in providing and arranging for a professionally produced event at the Ellipse." She was last paid by the Trump campaign on Nov. 15, a campaign spokesman said, adding that the campaign “did not organize, operate or finance the event" and any former staffers who worked on the event “did not do so at the direction of the Trump campaign."

Since April 2017, Wren and her Texas-based firm, Bluebonnet Consulting, have received more than $890,000 from the Trump campaign, the Republican National Committee and Trump Victory, the joint fundraising committee, FEC records show.

Chafian, a longtime organizer, said that in December she met Jones “by complete happenstance" at the Willard Hotel in Washington. Not long before, Chafian said, Jones had had a falling out with the leadership of Women for America First. Chafian, who is a reiki practitioner, said she was “put in a position, in my opinion based on what I know from the universe, to clear that energy. To clear that negativity."

Later that month, Jones contacted Chafian to discuss staging a January rally in support of an effort by Trump and his allies to overturn the election results and President Joe Biden's victory, she said. He subsequently directed her to Wren.

On Dec. 28, Chafian texted Wren that it was her understanding that Wren was now “handling all of the funding from here on out," and promising to get her the “budget and breakdown."

By the end of December, after Wren became involved in the organizing efforts, Chafian said that Wren brought in Women for America First and that Chafian was ultimately sidelined. By that point, she had had her own falling out with the Kremers, leading her to start her own group, The Eighty Percent Coalition, which held a rally at Freedom Plaza in Washington, D.C., on Jan. 5 that was largely sponsored by Jones. The guidance memo provided to VIP attendees of the Jan. 6 event informs attendees of Chafian's rally, inviting them to attend should they wish and noting that “registration is not required."

In a video released the day after the Jan. 6 event, Jones claimed an unnamed donor covered 80% of the roughly $500,000 it cost to put on the rally that preceded the Capitol riot.

The Kremers, Caporale and Jones have not responded to requests for comment.

Insiders at this Trump-favored charity are cashing in — and its financial reporting is questionable

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This election, one of President Donald Trump's most influential advocates is 26-year-old Charlie Kirk, who has developed a unique bond with the first family. The conservative star dines with the president at Mar-a-Lago and rang in the new year there. During each of the last two winters, he used the club to hold a formal fundraiser for his nonprofit, Turning Point USA, that featured Donald Trump Jr.

At a Turning Point event in June, the president, addressing the crowd, said, “Let us also show our appreciation to my good friend, Charlie. I'll tell you, Charlie is some piece of work who is mobilizing a new generation of pro-American student activists." On a Turning Point webpage soliciting donations, Trump Jr., a close friend of Kirk's, is quoted as saying, “I'm convinced that the work by Turning Point USA and Charlie Kirk will win back the future of America."

The tax-exempt charity says its mission is to educate “students about the importance of fiscal responsibility, free markets, and capitalism." As its profile has risen, its revenue has ballooned, reaching $28 million, a sevenfold increase in four years.

But behind the scenes, Turning Point USA has entered into questionable financial arrangements, particularly involving Kirk's mentor, William Montgomery, the lesser-known co-founder who is credited with discovering Kirk. Montgomery, 80, an Illinois entrepreneur and onetime Tea Party activist, is one of three Turning Point insiders who have won lucrative deals from the group to handle its printing, payroll processing and fundraising.

The nonprofit has also made misleading assertions about its finances to state and federal regulators, according to interviews and an examination of tax and business records.

Charities are required to conduct annual independent audits certifying their books are sound in order to fundraise in more than a dozen states. But the accounting firm Turning Point uses has engaged in multiple business relationships with Montgomery, who for years served as the nonprofit's treasurer. The dynamic, experts say, imperils independence and undermines the credibility of Turning Point's financial statements, including its federal tax returns — an issue of significance at a moment when more and more cash is flowing into the organization's coffers.

“This raises real questions about the legitimacy of the return," Philip Hackney, a University of Pittsburgh School of Law professor who formerly worked in the IRS' chief counsel's office, told ProPublica. “It makes it difficult to trust what is reported and begins to raise the possibility that it's a fraudulent statement."

The IRS requires, under the penalty of perjury, that charities attest whether they received an independent audit. Both Kirk and the co-founder have signed off on Turning Point's filings.

In response to questions from ProPublica, Sally Wagenmaker, an attorney for the nonprofit, said that payments to businesses belonging to organization officials “provided a compelling operational benefit in Turning Point's best and other interests," and that they were “in full compliance with TPUSA's IRS-compliant conflict of interest policy."

Andrew Kolvet, a Turning Point spokesman, said the business relationship between the group's auditor and its former treasurer is not significant and maintained the accounting firm is indeed an independent company. Another potential issue, ProPublica found, is that the license of the firm expired in late 2018, though the one that personally belongs to the firm's managing partner has not.

Turning Point was founded in 2012 by Kirk, then 18, and Montgomery, who invested in the young activist after hearing him speak at a small college in the state. At the 2016 Republican National Convention, Kirk met Trump Jr. and would soon accompany him on the road as an assistant. As Turning Point has thrived, Kirk's salary has grown from $27,000 to nearly $300,000, and he no longer lives with his parents — last May he bought a $855,000 two-bedroom, two-bathroom oceanfront condo in Longboat Key, Florida, county property records show.

Over the last year, the president has delivered remarks at the organization's conferences threeseparatetimes. At the group's December 2018 Mar-a-Lago affair, the president's eldest son helped it haul in nearly $5 million, tax records show. Recently, Kirk published a book called “The MAGA Doctrine," which Trump and his son promoted on Twitter.

For his part, Montgomery, whose Facebook profile picture features him posing with Trump Jr., left Turning Point last April, when, Kolvet said, his term as a board member ended. Two months later, Kirk effusively praised Montgomery in a blog post, celebrating his unmatched contributions to the nonprofit. “To anyone who has been impacted by my videos, podcast, TPUSA, our chapters, literature, events, conferences, field programs, or any speeches I have given," Kirk wrote, “you have Bill Montgomery to thank for investing in an 18-year-old with a vision — when everyone else thought it was impossible, foolish, and deemed for failure."

Montgomery, Kolvet told ProPublica, “remains a friend of the organization."

Turning Point amplifies White House messaging by regularly tweeting memes and one-liners supportive of Trump administration policies or politics to hundreds of thousands of Twitter followers, and it retweets similar messages sent by Kirk, who is followed by nearly 2 million people. Meanwhile, Kirk's and the group's tweets are often retweeted by the president, promoting the young leader's incendiary statements to more than 82 million followers, including his description of COVID-19 as the “China virus."

Kirk cultivates the image of a young, serious executive, favoring button-down shirts and sport coats in public. He revels in provoking left-leaning activists and students on everything from the Israeli-Palestinian conflict to the effects of “white privilege," which he calls a “racist lie." Turning Point promotes clips of his campus confrontations on social media, typically boasting that Kirk has “destroyed" an unworthy adversary.

Turning Point says it now has "a presence" on more than 2,000 campuses, 272 employees and an affiliated nonprofit largely focused on supporting Trump. Yet as the organization has expanded, it has on occasion been the center of controversy. Politico found that Turning Point has fabricated its influence on college elections. And in 2017, The New Yorker drew attention to an organizational culture that appeared plagued with racism and indifferent to laws that prohibit charities from engaging in express political advocacy. The magazine obtained text messages written by the group's former field director that said, “I HATE BLACK PEOPLE. Like fuck them all...I hate blacks. End of story." (The sender of the text resigned and Kirk told the magazine, “Turning Point assessed the situation and took decisive action within 72 hours of being made aware of the issue.")

ProPublica's examination of Turning Point's finances raises additional questions about the way the group is run, the reliability of its public disclosures and its approach to regulations governing nonprofits.

Turning Point is registered to fundraise in dozens of states across the country. Because of the group's size, attorneys general and secretaries of state in 15 states — including New York, Pennsylvania, New Mexico and Kansas — require it to file audits to remain in good standing. The work, each state's statute invariably specifies, must be carried out by “an independent certified public accountant."

The IRS does not require such an audit, but it asks about the audit's status. On Turning Point's last four federal tax returns, consistent with its state filings and spanning a period that covers July 2015 through June 2019, the group asserts that its financial statements are “audited by an independent accountant."

But Turning Point's accounting firm, the Stapleton Group, based in Orland Park, Illinois, has a significant tie to the charity. Montgomery, the charity's co-founder, has served as a “business development advisor" for Stapleton, helping to bring clients to the firm. The company's managing partner, Robert Stapleton, who handles Turning Point's returns, has worked as Montgomery's personal tax preparer, according to Stapleton. The firm, which employs a handful of people, was incorporated by the same suburban Chicago lawyer who, records show, formed a business entity Montgomery used to collect rent and make political contributions.

Robert Stapleton and the Stapleton Group did not respond directly to ProPublica. Instead, the firm provided comments through Kolvet.

Stapleton became Turning Point's auditor after Montgomery introduced the firm to the organization, a referral for which Montgomery wasn't compensated, Stapleton said through the spokesman. On his LinkedIn page and in a biography that once lived on Turning Point's website, Montgomery identifies his connection to Stapleton's firm; on the former, it states the affiliation began in 2010 and has continued to the present.

Montgomery received “no remuneration" from the firm and “acted in a business development capacity in his spare time and on commission only" in 2011, according to Stapleton. Turning Point, Kolvet said, “is confident in the independence of any services provided by The Stapleton Group."

In a statement, the firm said, “The Stapleton Group upholds the highest levels of integrity and independence while conducting audits and reviews for many businesses and organizations of all sizes."

Until the spring of last year, records show, Montgomery served on Turning Point's board and as its secretary and treasurer, giving him oversight of Turning Point's financial books and custody over its corporate records, according to the group's bylaws. At one point, he was solely responsible for fundraising and the spending of Turning Point's cash, according to charity records filed in New Mexico.

“If Montgomery has a strong relationship with the auditor, then there is a clear conflict there," said Tzachi Zach, an Ohio State University accounting professor. “Other than the auditor being hired, there should be no other relationship between the auditor and the nonprofit."

James Fishman, a former assistant attorney general in the New York attorney general's office, said that, on the question of independence, Turning Point's audit arrangement “does not pass the smell test. If an attorney general looked closely, they would find it wasn't independent."

In a letter dated July 7, and provided by Kolvet, Robert Stapleton wrote to Montgomery on company letterhead asking him to “immediately correct" his LinkedIn profile that claimed he is “associated with the Stapleton Group." The letter was dated two weeks after ProPublica first inquired about Montgomery's ties to the accounting firm; Montgomery's LinkedIn profile still identifies him as a “business development advisor" for Stapleton.

The nonprofit's most recent publicly available audit, signed by the “The Stapleton Group" in May 2019, presents an additional issue. The firm's license to practice expired in late 2018, according to the Illinois Department of Financial and Professional Regulation, the state agency that regulates occupational licenses. In Illinois, state law prohibits certified public accounting firms with an expired license from conducting audits.

Stapleton said his firm “is aware and is in the process of rectifying the issue," and through Kolvet provided a copy of his personal CPA license to ProPublica. Wagenmaker, the Turning Point attorney, wouldn't provide a copy of the group's most recent audit, which is not yet public and captures the nonprofit's finances through last July. She also wouldn't confirm whether it was carried out by the Stapleton Group.

Montgomery hasn't responded to calls and emails seeking comment.

During Montgomery's time at Turning Point, he personally benefited from several of the group's business arrangements. Between July 2017 and June 2019, tax records show, Turning Point paid more than $430,000 to a printing shop owned by Montgomery, and gave him an additional $25,000 for the rental of a small office space. The compensation was on top of the direct income he received from Turning Point, which earned him close to $200,000 during the same period.

Doug De Groote, the organization's board secretary, said the vendor payments to Montgomery “represent fair market value or lower for the trade services received." He added, “These decisions were made with Mr. Montgomery recused and with the organization's best interest paramount."

Turning Point similarly said it was getting a better deal by using the payroll processing firm owned by the organization's current treasurer, Tom Sodeika. In late 2018, the nonprofit tapped the services of his small, Illinois-based company, Precision Payroll of America. Turning Point paid Precision $51,072 for its services from late 2018 through last July, according to tax records. The amount, Kolvet said, was “at a significant discount below market rates and in full compliance with Turning Point conflict-of-interest policy."

In January, Sodeika sold the company and relinquished all executive positions there. Turning Point would not say how much Sodeika sold Precision for or to whom he sold it, but Kolvet told ProPublica that “prior to the sale of the company" it provided services to Turning Point “at discounted market rates."

Turning Point's treasurers are not the only insiders who have reaped financial rewards from the nonprofit. It also appears to have steered extra cash to a highly paid employee through limited liability companies, business records show.

Stacy Sheridan, Turning Point's “senior advancement director," receives a salary of more than $180,000, according to the group's latest tax filings, which also show over $200,000 flowing to two business entities — GSM Strategy LLC and Lionrock Ventures LLC — that were paid for fundraising. The return does not disclose who is behind both companies, neither of which has a website. But corporate records for GSM and Lionrock include Sheridan's name and addresses associated with her.

When asked about the LLC payments, neither Kolvet nor Sheridan provided a comment. On their own, the veiled arrangements may pass legal muster, but Hackney, the former IRS official, said they could be part of a larger, troubling pattern.

“As the number of self-interested transactions go up," he said, “the potential goes up for the possibility that the organization is being operated for the private interests of those who control the organization."

Trump campaign officials started pressuring Georgia's secretary of state long before the election

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Long before Republican senators began publicly denouncing how Georgia Secretary of State Brad Raffensperger handled the voting there, he withstood pressure from the campaign of Donald Trump to endorse the president for reelection.

Raffensperger, a Republican, declined an offer in January to serve as an honorary co-chair of the Trump campaign in Georgia, according to emails reviewed by ProPublica. He later rejected GOP requests to support Trump publicly, he and his staff said in interviews. Raffensperger said he believed that, because he was overseeing the election, it would be a conflict of interest for him to take sides. Around the country, most secretaries of state remain officially neutral in elections.

The attacks on his job performance are “clear retaliation," Raffensperger said. “They thought Georgia was a layup shot Republican win. It is not the job of the secretary of state's office to deliver a win — it is the sole responsibility of the Georgia Republican Party to get out the vote and get its voters to the polls. That is not the job of the secretary of state's office."

Leading the push for Raffensperger's endorsement was Billy Kirkland, a senior adviser to the Trump campaign who was a key manager of its Georgia operations. Kirkland burst uninvited into a meeting in Raffensperger's office in the late spring that was supposed to be about election procedures and demanded that the secretary of state endorse Trump, according to Raffensperger and two of his staffers.

When reached by phone, Kirkland directed the request for comment to the Trump campaign, which did not respond. The White House and the Georgia Republican Party also did not respond to repeated requests for comment.

Joe Biden has been projected as the winner of the presidential election in Georgia by a margin of roughly 14,000 votes. The state is now conducting a hand recount at the Trump campaign's request. Raffensperger's office has said that the recount won't swing enough votes to tip the state into Trump's column.

As the Georgia results have become increasingly clear, Republicans have unleashed intense criticism on the secretary of state's office, accusing it without evidence of mismanaging the election and allowing Biden to carry the state by fraudulent means. Georgia's U.S. senators, Republicans David Perdue and Kelly Loeffler, both of whom failed to win majorities for reelection on Nov. 3 and face Democratic opponents in January runoffs, called for Raffensperger's resignation. All of the Republicans representing Georgia in Congress also signed a letter sent to Raffensperger's office from the personal email account of the chief of staff to U.S. Rep. Earl “Buddy" Carter, criticizing the office for a series of supposed irregularities.

Rep. Doug Collins, who recently lost a bid for Loeffler's Senate seat, has been particularly vocal. On Monday, Collins tweeted, “In a year of political division in Georgia, few things have unified Republicans and Democrats — one of them is Brad Raffensperger's incompetence as Secretary of State." Raffensperger has reserved some of his sharpest responses for Collins, calling him a “failed candidate" and a “liar" on social media.

On Monday, The Washington Post reported that Lindsey Graham, a Republican senator from South Carolina, had phoned Raffensperger to see if the secretary of state had the authority to toss out legally cast ballots. Graham has said that he was simply asking how the process works. Two members of Raffensperger's staff who were on the call told ProPublica that the secretary of state's account was accurate and that they were appalled by Graham's request.

Raffensperger said that the Trump campaign “scapegoated" him. Its contention that he ineffectively managed the election amounts to “hot air and hyperbole," he said. “In Georgia, it is not new to see failed candidates claim fraud or suppression. At the end of the day, the Trump campaign's messaging didn't resonate with 50% plus one of the voters."

The campaign's formal efforts to gain the secretary of state's endorsement began on Jan. 10, when Kirkland emailed Deputy Secretary of State Jordan Fuchs, assuming that Raffensperger would welcome the opportunity to serve in an unofficial role. “We are getting ready to release the campaign's statewide leadership team and wanted to make sure you were good to be listed as an honorary co-chair?" he wrote, according to an email obtained by ProPublica. At the direction of Raffensperger, Fuchs declined.

“It is our standard practice not to endorse any candidate. This policy is not directed at any specific candidate, but all candidates, as the Secretary oversees elections and the implementation of new voting machines here in Georgia," she wrote.

Kirkland has a long history in Georgia Republican politics. He has also worked for the Trump White House — first in the Office of Intergovernmental Affairs and then for Vice President Mike Pence. He left the White House in the fall of 2019 to become a Georgia-based senior adviser to the Trump campaign. He also serves as a senior adviser to Pence's leadership PAC. FEC filings show that Kirkland is paid for consulting by the Trump campaign and the Republican National Committee. Loeffler hired Kirkland to be her campaign manager in January.

It's not unusual for candidates to ask for the endorsement of state elected officials, including secretaries of state, said veteran Republican elections attorney Ben Ginsberg. “But usually, campaigns accept the answer they are given if they know how to behave," Ginsberg said.

The Trump campaign did not accept Raffensperger's refusal. After Raffensperger announced that his office would mail absentee ballot applications to every registered voter in the state ahead of its June primary, a move opposed by the Trump campaign, the executive director of the Georgia Republican Party, Stewart Bragg, requested a meeting. He told Raffensperger's staff that he wanted to discuss election law and outstanding public records requests for voter data filed by the party.

Kirkland crashed the meeting shortly after it began. “A lot of people have noticed you didn't endorse," he said, according to two staffers. Raffensperger again made clear that any endorsements were against office policy, he told ProPublica.

Raffensperger had to leave the meeting early for another event. When the meeting came to a close, one of his staffers offered to continue the conversations at a later date and asked if there was any additional publicly available voter data that the party needed. “We'll see how helpful you are in November," Kirkland said, before leaving the office and slamming the door behind him, according to the staffers.

Trump has repeatedly and baselessly questioned the Georgia results on Twitter, accusing both the secretary of state's office and Republican Gov. Brian Kemp — a Trump loyalist who, unlike Raffensperger, did agree to be an honorary campaign co-chair — of coordinating with activist and former Democratic gubernatorial candidate Stacey Abrams to make Georgia's elections less secure.

“The Consent Decree signed by the Georgia Secretary of State, with the approval of Governor \@BrianKempGA, at the urging of \@staceyabrams, makes it impossible to check & match signatures on ballots and envelopes, etc. They knew they were going to cheat. Must expose real signatures!" Trump tweeted over the weekend.

Nothing about the consent decree — which was aimed at addressing the disparity in signature matches among racial groups — prevents clerks from verifying signatures. Raffensperger said his office has repeatedly and publicly explained the process for signature matches, and he laughed at the idea that he would coordinate with Abrams, who has criticized his office over issues such as long lines at the polls in minority neighborhoods in prior elections.

Trump and the Republican legislators have pressed their allegations even as the National Republican Senatorial Committee has distributed talking points implicitly acknowledging that Biden won the election, according to an internal memo obtained by ProPublica. That message contrasts with what Trump, his campaign and his administration are telling supporters.

The memo was circulated last week among Georgia field staff, who are preparing for two runoff elections in January that will determine which party controls the upper chamber. It contains a series of “key" talking points directed at prospective voters. One says that the Democratic candidates, Raphael Warnock and Jon Ossoff, “are funded by out of state liberals because they'll be a rubber stamp for their radical agenda to defund the police, open our borders, and pack the courts." Another states that, should Warnock and Ossoff get elected, “Chuck Schumer and Nancy Pelosi will have the votes they need to transform our country into a socialist state."

The talking points omit any mention of Biden, but none of the outcomes outlined by the NRSC, which did not respond to requests for comment, would be possible with a Republican president.

Raffensperger expressed frustration at the lack of action by Republicans from the White House down to proactively address issues of election integrity. “If Trump and Collins were concerned about voter fraud, they would have proposed and passed legislation to fix it." Instead, he said, “they did nothing, absolutely nothing."

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Top FEC official's undisclosed ties to Trump raise concerns over agency neutrality

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

Debbie Chacona oversees the division of the Federal Election Commission that serves as the first line of defense against illegal flows of cash in political campaigns. Its dozens of analysts sift through billions of dollars of reported contributions and expenditures, searching for any that violate the law. The work of Chacona, a civil servant, is guided by a strict ethics code and long-standing norms that employees avoid any public actions that might suggest partisan leanings.

But Chacona's open support of President Donald Trump and her close ties to a former Republican FEC commissioner, Donald McGahn, who went on to become the 2016 Trump campaign's top lawyer, have raised questions among agency employees and prompted at least one formal complaint. Chacona, a veteran agency staffer who has run the FEC's Reports Analysis Division, or RAD, since 2010, has made her partisan allegiance clear in a series of public Facebook posts that include a photo of her family gathered around a “Make America Great Again" sign while attending Trump's January 2017 inauguration.

The public display of partisanship bewildered some FEC staffers, according to a former agency employee. For decades, the agency expressly banned employees from engaging in such partisanship, a cultural ethos that has stuck even after those rules were relaxed in 2011. Chacona's duties included discerning whether the inaugural committee's disclosures of donor information appeared to contain any “serious violations" of the law, an FEC procedures manual states.

Tyler Culberson, who worked under Chacona as a senior campaign finance analyst from 2010 to 2015, told ProPublica that staffers were trained to never betray political preferences that could call into question their division's “neutrality."

“Any public display of support or opposition to any candidate, campaign, anything on the federal level — we didn't do it," Culberson said. “When you are regulating partisan committees, the display of partisanship suggests the possibility of preferential treatment to that committee or candidate. So the mere appearance of it is problematic."

The inaugural committee, a nonprofit distinct from Trump's presidential campaign, filed its initial 510-page report in April 2017, detailing a record-breaking $107 million raised from more than 1,000 contributors. Within two weeks, a news story and then a watchdog complaint filed with the FEC highlighted a host of misidentified and shady donations. Several months later, when the committee amended its filing to address the issues, Chacona ultimately signed off on it, records show. But the updated report continues to list donors whose addresses don't exist in public records. The committee has had other problems too: State prosecutors have accused it of spending lavishly on Trump properties, and federal investigators subpoenaed the nonprofit for donor records in an effort to track down any illegal contributions made by foreign nationals.

Separately, emails and other records obtained by ProPublica show Chacona had frequent, friendly interactions on matters professional and personal with McGahn. The two worked together at the agency from 2008 through September 2013, when McGahn briefly entered private practice then went to work in 2015 as counsel for Trump's presidential campaign. After the election, he served as White House counsel.

Chacona did not respond to requests for comment. McGahn said, “I don't comment on nonsense."

Over the course of McGahn's FEC tenure, concerns over his ties with Chacona were relayed through official agency channels: at least one colleague complained directly to Chacona's supervisor that her closeness to the attorney could undermine the agency's nonpartisan credibility, and the relationship was the backdrop for a 2011 inspector general report that was shared with commissioners.

The emails between Chacona and McGahn, obtained by ProPublica through the Freedom of Information Act, show that Chacona sought McGahn's advice on fine points of campaign finance law and regulation, and engaged in derogatory exchanges about Ellen Weintraub, a Democratic FEC commissioner, and Fred Wertheimer, one of the country's leading advocates for campaign finance reform. Democracy 21, Wertheimer's nonprofit, helped file the FEC complaint against Trump's inaugural committee.

Larry Noble, a former FEC general counsel who served in Republican and Democratic administrations, told ProPublica that an official in Chacona's position must be “fair" to all commissioners, and that expressing negative views to a commissioner about someone with business before the agency “raises questions about whether the person will get a fair shake."

Noble added that, overall, it's “inappropriate for the head of a division to have such a relationship with just one commissioner. It makes you wonder in what ways she's steered RAD toward that ideological view in both subtle and obvious ways — what kind of things the division went after, and what kinds of things it didn't."

Chacona's division provides the public's only window into how money is spent and raised on elections. She manages a staff of 70 employees, a portion of whom flag irregular contributions and potential spending violations that can prompt audits, civil penalties and, in rare cases, criminal prosecutions.

Culberson said that Chacona is “ultimately the one who will say, 'We're not going to question this; we are going to question this.' There is a level of putting her finger on the scale if she wanted to."

It is unclear whether the Trump campaign has received favorable treatment from Chacona. The FEC declined to address detailed questions from ProPublica, including whether Chacona and McGahn communicated about campaign finance issues during the 2016 election cycle, interactions that would introduce the prospect of favoritism.

Ann Ravel, a Democrat who served on the commission, said Chacona's show of support for the president and the emails detailing her consultations with McGahn warrant an internal investigation to determine if there was any wrongdoing.

“You assume everything Debbie is saying is based solely on her expertise and knowledge," she said. “At the very least, she should never, at any point, be involved in any decisions relating to Trump."

Chacona's contacts with McGahn may have run afoul of a government ethics regulation meant to address circumstances in which close relationships can call into question an employee's decision-making, said Kathleen Clark, a government ethics expert at the Washington University School of Law in St. Louis. That rule requires that employees get approval from a designated agency official in cases where a “reasonable person with knowledge of the relevant facts" might question the federal employee's “impartiality."

McGahn is not involved in the president's 2020 campaign, according to Tim Murtaugh, the campaign's communications director. He is now a partner at Jones Day, a Washington, D.C., law firm that has been paid millions of dollars this cycle by the campaign.

Murtaugh declined to say whether the campaign was aware of McGahn and Chacona's relationship in 2016, if the two were in touch over disclosure filings that year or if the campaign is in communication with Chacona now.

“As Usual, You Schooled Me"

The tenure of McGahn, appointed to the FEC by President George W. Bush, was punctuated by discord between Republican and Democratic commissioners. Known as pugnacious and relentlessly partisan, McGahn led the agency's GOP wing as it regularly pushed back on campaign finance regulation. Votes on possible violations often resulted in a 3-3 deadlock as commissioners split along party lines, a lasting legacy that has earned him the reputation as one of the panel's most influential members of all time.

The acrimonious dynamic was exacerbated by the Supreme Court's controversial 2010 Citizens United decision, which laid the foundation for removing essentially all limits on corporate and nonprofit election spending, as well as lifting restrictions on individual contributions to political action committees.

As elections were flooded with far more money than ever before, the importance of Chacona's division grew.

In this uncharted regulatory terrain, she looked to McGahn for guidance.

“Wondering if a Super PAC that contributes to another Super PAC is still held to the contribution limit," Chacona asked McGahn in the summer of 2012, her email including a smiley face. “Your thoughts please."

“No limit," he responded.

Part of the exchange is redacted, so it's unclear where Chacona landed on the matter, but in her final response to him she said that “I even thought of some of what you said on my own (probably from reading all of your stuff over the years)."

The trove of emails shows that she shared McGahn's negative view of those who saw Citizens United as a potential danger to democracy.

In early 2010, Chacona and McGahn privately mocked Wertheimer, whose watchdog group, Democracy 21, often files FEC complaints. In a press release, Wertheimer contended that the Citizens United decision was “out of touch with the American people."

Chacona forwarded the quote to McGahn, wondering if Wertheimer “ever talked with anyone outside the beltway about this stuff," because, she said, “they pretty much don't have a clue." Chacona concluded, “Sounds like he's the one out of touch," ending the sentence with another smiley face.

McGahn replied that Wertheimer has “zero intellectual honesty, and will say anything about anyone."

The contempt extended to Weintraub. In one 2011 exchange, the two discussed a Politico article that quoted Weintraub as saying she considered the Republican panelists “colleagues" and “not pals," prompting Chacona to ask, with her customary smiley face, “How broken up are you that Ellen doesn't consider you a pal?"

Chacona told McGahn, who was quoted in the story deriding “superficial compromise," that he came across as “sensible and sincere."

McGahn responded that to Weintraub a deadlocked commission vote is “a failure to give guidance, but [to] everyone else, it's a green light."

A year later, early in what would become a more than $2 billion presidential contest between Mitt Romney and President Barack Obama — then the most expensive race in American history — Chacona and McGahn were critical of journalists scrutinizing FEC disclosure reports. She wrote to him decrying a “media frenzy" over the issue. McGahn characterized the intense interest as “disclosuremania."

The emails show Chacona held McGahn in high regard. “As usual, you schooled me," she wrote in one exchange about the Supreme Court and campaign finance. In an email about disclosure rules, she told him, “I should know by now you are always a step (or 2, 3, 4…) ahead."

“A Bit Too Cozy"

Chacona's closeness to McGahn prompted at least one top FEC official to complain to Chacona's supervisor, Patricia Orrock, about the appearance of a potential conflict of interest that could jeopardize the agency's integrity.

Lynn Fraser, who retired in May 2017 as the head of the FEC's Alternative Dispute Resolution program, told ProPublica that she was troubled by interactions between the RAD official and the commissioner, which she described as “a bit too cozy."

Fraser said she spoke up because the appearance that the head of RAD had a personal or political bias for McGahn, a staunch Republican, could hurt the division's promise of neutrality and might unintentionally influence RAD analysts worried about challenging a boss with a clear point of view.

“Conflicts of interest are tricky little things because sometimes people don't even realize they have a conflict, they don't perceive it as such," Fraser added. “And that's actually more dangerous. It can color your worldview without you even being really aware of it. And Don was persuasive. He's really smart. And he knows campaign finance."

In a closed door meeting, while McGahn was still a commissioner, Fraser said she asked Orrock to explain to Chacona that her relationship with the commissioner “looks really bad."

“It's the appearance of impropriety that starts raising peoples' concerns," Fraser said she remembers telling Orrock, who remains Chacona's supervisor. “I got the assumption, and that's all it was, that she would say something to Debbie."

It's not clear whether Orrock, who did not respond to a request for comment, ever talked with Chacona.

Fraser's concerns did not come in a vacuum. In 2011, Chacona's husband, Marcus, lodged a complaint with the FEC's inspector general. The complaint included allegations that he had received anonymous calls relating to his wife and McGahn.

“The nature of this contact is to apparently alert me about the nature of their relationship and they expressed that it is more than professional," he wrote.

The resulting report, which was shared by commissioners, was unable to determine who was behind the calls because Marcus Chacona, who declined to comment, stopped cooperating and refused to turn over his phone records.

A Look at the Trump Inaugural Committee's Filing

Almost as soon as Trump was inaugurated on Jan. 20, 2017, reporters noted the crowd size at the event was smaller than it was for Obama's first inauguration in 2009. The accurate assessment touched off days of blustery pushback from the White House, which took on the media over its inaugural coverage. Chacona posted an image on Facebook of the event showing a packed crowd on the National Mall. “Here's a real picture from yesterday," she wrote.

But while the dispute played out publicly, more significant problems faced the 58th Presidential Inaugural Committee.

The nonprofit group had raised more than double what Obama's inaugural committee collected in 2009, and the FEC required it to account for its donors. When Trump's committee filed its initial FEC disclosure form in April 2017, the Huffington Post created a public spreadsheet to crowdsource its effort to vet the names, companies and addresses.

Within days, the news outlet detailed hundreds of reporting mistakes, such as obscuring the true buyer of inaugural tickets and disclosing inaccurate donor addresses.

A week after the story was published, Wertheimer's Democracy 21 and other watchdog groups filed a formal FEC complaint, arguing that inaugural officials had recklessly filed reports “they knew or should have known did not include required information."

Trump's committee amended its filing to address some problems and asserted that the complaint raised mostly “technical reporting issues" and should be dismissed. To support its argument, the committee noted that RAD had sent both of Obama's inaugural committees formal requests for more information — inquiries the Obama committees satisfied by amending their filings.

The FEC general counsel sided with Trump's committee in an October 2017 report and recommended the commission dismiss the complaint. While acknowledging that “we do not know the full extent of the Inaugural Committee's inaccurate reporting," the report concluded that the Trump committee had made “analogous errors" to those of Obama. “We do not believe it is an efficient use of Commission resources to pursue this matter," it said.

In a footnote, the report explicitly states that Chacona had “discretion" over the Trump committee's amended report, and that RAD chose not to formally request more information.

Years later, the Trump inaugural has still not resolved all of its reporting problems, and the committee continues to list donors with questionable addresses, according to an examination by CNBC. One $25,000 donation, for example, came from a Singapore address that does not appear in public records. It is illegal for an inaugural to accept donations from a foreign national, but in its report, the Trump committee asserted that the donor was an American citizen. An additional $100,000 came from a contributor whose Anaheim, California, address also could not be verified. Both discrepancies were confirmed by ProPublica.

An inaugural committee spokesman said that if “additional corrections" to its report “are ever required, they will be addressed." He also said that McGahn played no role in responding to Democracy 21's complaint.

Wertheimer, who had been ridiculed by McGahn and Chacona years earlier, told ProPublica that he “can't see any reasonable explanation" for why RAD hasn't asked the inaugural committee to resolve these discrepancies. He said the FEC should “look at whether this was a political decision or a policy decision that can be justified."

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