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President Trump and his allies are waging war with the Federalist Society as he sees parts of his second-term agenda blocked by some of his own judicial appointees.
Simmering tensions broke into full public view after Trump called longtime Federalist leader Leonard Leo a “sleazebag” after a court blocked the bulk of Trump’s tariffs.
The boiling point has unleashed a rebellion pitting the Make America Great Again movement against the conservative legal stronghold that helped Trump reshape the courts during his first term by offering up conservative judges as suggestions to fill benches across the country.
As the president embarks on choosing his next set of judicial nominees in his second-term, his decisions are now being shaped by a new, MAGA-branded team.
Inside the White House, judicial appointments are being spearheaded by chief of staff Susie Wiles, White House counsel David Warrington and Deputy White House counsel Steve Kenny.
The Federalist Society once played a central role in advising Trump’s White House on those decisions. But in the president’s second term, the process has shifted to include outside influence from the Article III Project, which is spearheaded by close Trump legal ally Mike Davis.
Davis served as chief counsel for nominations to Senate Judiciary Chairman Chuck Grassley (R-Iowa) during Trump’s first term, where in that role he helped clear the way for the president’s judicial nominees. David also previously clerked for Supreme Court Justice Neil Gorsuch, Trump’s first nominee to the high court. His relationship with Trump grew closer after the FBI raided the president’s Mar-a-Lago resort and he defended the president in the press.
Meanwhile, the Federalist Society looked the other way, Davis said in an interview with The Hill.
“They abandoned President Trump during the lawfare against him,” he said. “And not only did they abandon him — they had several FedSoc leaders who participated in the lawfare and threw gas on the fire.”
It’s a major shift from Trump’s first term, when Trump’s alliance with Leo was bountiful.
Trump ushered in a Supreme Court 6-3 conservative supermajority that left Federalist Society panelists popping champagne at one recent convention to celebrate their success.
Leo built the lists that Trump chose from to select his three high court nominees: Gorsuch, Brett Kavanaugh and Amy Coney Barrett.
The three justices have delivered significant wins for the conservative legal movement, including expanding the Second Amendment, overturning the constitutional right to abortion, reining in federal agency power and reinforcing religious rights.
It culminated decades of efforts by Leo to challenge liberal legal orthodoxy by building a pipeline that propels young conservative attorneys into powerful judicial roles.
Fueled by a network of donors, Leo’s groups have directed massive sums to conservative legal, political and public relations organizations, gaining him a villainous reputation among Democrats.
The Federalist Society has become a bastion of that project, with Leo serving as its longtime former executive vice president.
Formed in 1982 by a group of law students opposed to liberal ideology at prominent law schools, the Federalist Society has become a dominant force, though it officially takes no position on any legal or political issue as a 501(c)3 nonprofit.
But Trump is souring on the group in his second term as he expresses frustration with his judicial picks who’ve blocked parts of his agenda.
Last week, the president turned his ire toward Leo and the Federalist Society after the U.S. Court of International Trade blocked the bulk of his tariffs.
“I was new to Washington, and it was suggested that I use The Federalist Society as a recommending source on Judges,” Trump wrote in a winding post. “I did so, openly and freely, but then realized that they were under the thumb of a real ‘sleazebag’ named Leonard Leo, a bad person who, in his own way, probably hates America, and obviously has his own separate ambitions.”
In a statement responding to the attack, Leo declined to attack Trump, instead praising him for “transforming” the federal courts and calling it the president’s “most important legacy.”
Trump’s post went on to slam the Federalist Society for the “bad advice” it gave him on “numerous” judicial nominations.
“This is something that cannot be forgotten!” Trump said.
A Federalist Society spokesperson did not return multiple requests for comment.
It remains unclear why Trump specifically targeted Leo in his response to the tariff ruling.
The trade court panel included one of Trump’s own appointees, Judge Timothy Reif. Reif is a Democrat, as federal law required Trump to keep partisan balance on the trade court.
Steven Calabresi, who co-chairs the Federalist Society’s board with Leo, submitted a friend-of-the-court brief in the case alongside other prominent conservative attorneys calling Trump’s tariffs unlawful.
And the New Civil Liberties Alliance, a libertarian group that has received funding from entities associated with Leo, is suing Trump over his China tariffs on behalf of a small business, though that case was not the subject of last week’s ruling.
But the splintering relationship between Trump and the Federalist Society has been “brewing for years,” Davis said.
In January, allies of the president grew outraged online after Politico reported that a public relations firm chaired by Leo was assisting an advocacy group founded by former Vice President Mike Pence in a campaign to derail Health and Human Services Secretary Robert F. Kennedy Jr.’s nomination.
Pence defended Leo and the Federalist Society on X Monday, calling them “indispensable partners” throughout Trump’s first term and suggesting conservative Americans owe the group a “debt of gratitude.”
And beyond the cabinet, some prominent conservative attorneys have criticized Trump’s nomination of Emil Bove, a close legal ally who worked as Trump’s former criminal defense attorney, to a federal appeals court.
Ed Whelan, a Federalist Society mainstay and prominent conservative attorney who has been critical of Trump, has particularly gone after Trump’s nomination of Bove, describing the attorney as a bully.
“Bove’s admirers call him ‘fearless,’ but the same could be said of mafia henchmen,” Whelan wrote for the National Review.
Whelan’s comments sparked rebuttals from the top levels of Trump’s Justice Department.
Deputy Attorney General Todd Blanche, who represented Trump with Bove, accused Whelan of being envious, saying he was leveling “cheap shots.” Harmeet Dhillon, who leads the Justice Department’s civil rights division, called it one of “dumbest and nastiest headlines” she had ever seen.
“Some small minded men appear to be jealous and bitter that the best they can do is dictate their unedited mean girl thoughts into their phones and have some other mean girls publish the same,” Dhillon wrote on X.
Trump’s second term presents another chance to elevate conservative-minded judicial nominees nationwide. Davis said there’s no going back to the 2016 playbook.
“We have to update our playbook, and we have to have a different prototype for judges,” he said. “They need to be bold and fearless, like Emil Bove.”
“And I’m not saying they need to be bold and fearless for Trump, he added. “They need to be bold and fearless for the Constitution.”