Federalist Society leader’s 'lavish' lifestyle under scrutiny after $43 million dark money transfer

Leonard Leo, the right-wing leader of the judicial activist network the Federalist Society, is coming under scrutiny for his "lavish" use of the organization's funds to live the high life, POLITICO reported on Wednesday.

"A network of political non-profits formed by judicial activist Leonard Leo moved at least $43 million to a new firm he is leading, raising questions about how his conservative legal movement is funded," reported Heidi Przybyla. "Leo’s own personal wealth appeared to have ballooned as his fundraising prowess accelerated since his efforts to cement the Supreme Court’s conservative majority helped to bring about its decision to overturn abortion rights. Most recently, Leo reaped a $1.6 billion windfall from a single donor in what is likely the biggest single political gift in U.S. history."

Leo has been a massively influential figure, often called Trump's "judge whisperer" for the outsized role he played in getting right-wing jurists seated who have been involved in everything from dismantling abortion rights, to rolling back voting and redistricting protections, to undermining the regulatory process.

According to POLITICO, which has obtained records of Leo's finances over the last two decades, Leo's personal wealth skyrocketed under President Donald Trump, with whom he worked closely to appoint a steady stream of right-wing judges to the federal bench including three at the Supreme Court — "the same period during which he erected a for-profit ecosystem around his longtime nonprofit empire that is shielded from taxes."

CRC Advisers, the consulting firm he created in 2020, did not respond to questions about what the $43 million is being used for. However, Leo, who led a "middle class lifestyle" prior for most of his time at the Federalist Society, began making extravagant purchases after the former president's election in 2016, including "two new mansions in Maine, four new cars, private school tuition for his children, hundreds of thousands of dollars in donations to Catholic causes and a wine buyer and locker at Morton’s Steakhouse."

Stetson University law professor Ciara Torres-Spelliscy, an expert on campaign finance, told POLITICO, “If millions of dollars in dark money are sloshing around, it makes it really easy for people on the inside to take a cut ... That behavior is, unfortunately, now showing in the judicial nominating process."

This is not the first time questions have been raised about Leo's financial activities. In 2019, The Washington Postflagged that Leo has helped right-wing nonprofits raise $250 million to promote his approved judges, with no transparency in the donors' identity. And another dark-money group, BH Ventures, which contributed $24 million to CRC Advisors and up to $5 million to former Trump adviser Kellyanne Conway's polling firm, shut down shortly after reporters began investigating it.

Alarmed Democrats have responded in force to the Federalist Society's efforts to remake federal courts. Since taking office, President Joe Biden has been confirming judges at an even faster pace than Trump did, with 97 seated in his first two years alone — often from a diverse array of racial and professional backgrounds.