Interviews with people familiar with the inner workings of the Federalist Society, including two board members, paint a picture of a symbiotic relationship in which Leo uses his connection to the society’s vast network of academics to gain credibility with donors. , who then contribute to dark money operations that engage in the kind of partisanship that society officially avoids.

Leo’s political activism and his use of donor money to enhance his own wealth have sparked growing tensions between him and his co-chairman, Northwestern University law professor Steven Calabresi, and Meyer, who has been CEO or chairman for more than 30 years. according to three people familiar with the society. But they said Leo’s ties to the conservative donor base fear a break would leave the society scrambling for funding, while members also worry that any break in the facade of the conservative legal movement would only empower liberals who all parties disdain.

Leo’s business empire and leadership position in society «are easily blurred,» creating «a public relations problem,» said Professor Lloyd Hitoshi Mayer, a nonprofit advocacy expert at the University of Notre Dame. .

Society must decide whether Leo’s «personal activities» have become damaging enough to his image for him to leave, he said.

“That can happen in a quiet way,” with Leo agreeing to go, “or it can happen in an ugly way, with that person threatening to take donors with them or publicly slandering them,” said Mayer, who appears as a collaborator on the society’s website, which means that he participated in events.

Society is still very dependent on the Leo network. He received $5.6 million in grants in 2020 and $3.5 million in 2021 from The 85 Fund, a renowned dark money group Leo has said he plans to use to fund conservative causes across the country, according to federal disclosures. This makes the Federalist Society the second largest beneficiary of Leo’s main dark money vehicle, aside from the Donors Trust, another conservative non-profit organization.

Calabresi and Meyer did not respond to requests for comment. Indicating the close professional relationship between the Federalist Society and Leo’s for-profit companies, a spokesperson for Leo’s new for-profit company, CRC Advisors, sent POLITICO a statement on Meyer’s behalf. “Leonard Leo did an outstanding job at the Federalist Society for 20 years and we are extremely grateful for his faithful service,” Meyer said in the emailed statement.

Seven other board members contacted by POLITICO declined to comment or did not respond to requests for comment about Leo’s activities.

One board member, granted anonymity to freely discuss a sensitive issue, defended Leo’s dual role as activist and society leader. The board member said others in the organization have similar dual loyalties, pointing to David McIntosh, another Federalist Society co-founder and current board member who is also president of the Club for Growth, which spends heavily on House campaigns. and the Senate through their political affiliates. action committees. The Club also paid for ads related to Trump’s Supreme Court picks.

But critics, including some within the society, point out that Leo’s dual arrangement provides a possible endgame around bans on political activity by educational nonprofits, with the prestigious debating society attracting donors and I read by raising the funds through politically active independent groups.

«The vast majority [of Federalist Society members] is in this debating society mode, and then you have this person [Leo] which is a bit influential in a different way,” said a longtime member, who was granted anonymity to speak freely on a sensitive issue.

Leo seems to be planning to use Seid’s money to create a new ecosystem of conservative activism which you are comparing to a Federalist Society for cultural institutions, from schools to boardrooms. The fact that he and a small circle of his friends appear to be getting richer in the process stands in further contrast to many of the largely academic members of the society who have spent 40 years building the group’s pedigree as the premier debating society of the nation, which is above the political fray.

Seid did not respond to a request for comment.

Leo’s dual roles have served to attract a key backer: Trump. As a presidential candidate in 2016, Trump promised that his nominees would be «everyone» [be] elected by the Federalist Society. However, according to a person with direct knowledge of the situation, the list of Supreme Court nominees that Trump relied on to create a conservative supermajority was devised solely by Leo. Neither the top brass of the organization nor the directors of the board had any official role in drawing it up.

It’s another example of how Leo’s association with society helped Leo build his brand with donors and politicians.

“There has always been a tension” between society’s academic majority and Leo’s lucrative giant, the person said. Now, the society member says, Leo’s role in creating the vast majority of the court has created unwanted challenges for society. This includes trouble lining up Democrats or more moderate speakers to participate in their events due to ill-feeling toward Leo, the member said.

“The Society has a strong reputation for hosting speakers from all sides of the ideological spectrum,” it boasts on its website.

Steven Teles, a professor of political science at Johns Hopkins University and author of a book on the rise of the conservative legal movement, including the Federalist Society, agreed.

“The tension that was always there may have become more impossible to handle, but it was always there,” he said.

In 2020, that tension seemed to surface when Leo left the company’s payroll as deputy director, in a move that seemed designed to separate him from the day-to-day dealings of the company. But at the same time he has continued to reign as co-chairman alongside Calabresi, who is widely considered a thought leader in conservative legal circles.

The rise of Leo’s dark money groups has coincided with an increase in his personal wealth and an expansion of his lavish lifestyle, beginning in 2016 when Trump took office, as POLITICO previously reported.

During this period, Leo’s network also facilitated millions of dollars in combined payments to at least two co-workers at the Federalist Society, who have since joined him in his private company, CRC Advisors. An entity that includes Maria Marshall, formerly the company’s COO, as its sole officer received $775,000 over three years from the Leo-connected Rule of Law Trust, while Jonathan Bunch, now president of CRC Advisors, received $1.54 million from the same non-profit organization. , which lists Leo as his main officer, according to federal disclosure forms.

Bunch and Marshall did not respond to requests for comment, and CRC «will not provide additional comment» on the matter, spokesman Adam Kennedy said.

Leo also appears to have used his network to pay between $1 million and $5 million to Trump adviser Kellyanne Conway for the sale of her business while advocating for Leo’s list of preferred court nominees, raising concerns. among ethicists and led to at least one complaint from a liberal watchdog group that called on Congress to investigate.

The dark money group Leo used to facilitate the transaction, the BH Fund, dissolved days after POLITICO inquired about its role in facilitating the sale of Conway’s polling firm.

A second for-profit entity linked to Leo also dissolved almost at the same time. The Barton Group, registered at the same address as Leo’s BH Fund, received $2.59 million from the same non-profit organization, the Rule of Law Trust, which lists Leo as its chief officer. Virginia State Corporation Commission files show that, along with the BH Fund, the Barton Group also dissolved days after the POLITICO story broke in December.

The Federalist Society, an organization of 60,000 lawyers, law students and academics, has made it clear that does not lobby, take political positions or sponsor or endorse political candidates.

But the philosophical distance between its top leaders couldn’t be more apparent.

Calabresi, who has remained an academic and unpaid leader of the Federalist Society, has spoken out on the politicization of the high court and, in 2020, publicly discussed for periods of justice of 18 years.

On October 24, 2022, Calabresi co-authored an amicus curiae brief in Moore vs. Harper arguing against the idea that state legislatures could act without any checks in regulating federal elections. Traditionally conservative organizations, such as the Rutherford Institute and the Niskanen Center, co-authored a similar amicus curiae brief with the ACLU.

These briefs are opposed by several filed in support of the petitioner and linked to Leo and the sponsors of the Federalist Society, including the Honest Elections Project, the Claremont Institute Center for Jurisprudence, Citizens United, and the American Legislative Exchange Council.

More broadly, Leo became a fixture advising Trump on judicial appointments that coincided with a loss of confidence in the court.

Meanwhile, Calabresi called for Trump’s removal, twice. in a July 2020 opinion piececalled Trump’s suggestion to delay the November 2020 election «unconstitutional.» Calabresi Called for Trump’s removal again on January 12, 2021, following the January 6 riots at the US Capitol.