When Donald Trump described Leonard Leo, his top judicial confidant, as a “real sleazebag” in a social media post this week he thrust into the open divisions within the conservative legal movement that could shape the rest of his presidency.
During Trump’s first term, the president joined forces with Leo, co-chair of the powerful Federalist Society, to stock the federal judiciary with 226 conservatives, including three members of the US Supreme Court.
But now some of those judges as well as Federalist Society members appointed by earlier Republican presidents are refusing to rubber stamp Trump’s most controversial actions. On Thursday, two Republican appointees to the Court of International Trade joined with a Democrat to block Trump’s signature tariffs.
Leo is “a bad person, who in his own way, probably hates America,” Trump wrote on Truth Social after the ruling. “I am so disappointed in The Federalist Society because of the bad advice they gave me on numerous Judicial Nominations.”
The comments highlight a fissure in the conservative legal movement as Trump pushes the boundaries of presidential power. His loyalists are demanding that judges toe the line, while traditional conservatives push back against measures they find unconstitutional.
“To Trump, loyalty über alles [above all],” said Barbara Perry, professor of presidential studies at the University of Virginia’s Miller Center. “This may be a rift that’s not mendable in Trump’s mind”.
Republicans in Congress have largely gone along with Trump’s efforts and the Democrats are in disarray, leaving the courts as the main check on Trump’s power. The most important cases will end up at the Supreme Court, where the balance of power is held by the three Trump appointees.
One of them, Amy Coney Barrett, has already come under attack from conservatives for her deciding vote in March that forced Trump to release foreign aid funds that he was withholding. Online critics also claimed she looked “side-eye” at the president while attending his annual speech to Congress.
As the legal challenges to Trump’s efforts to concentrate power mount, pressure is rising on legal conservatives steeped in longtime constitutional norms.
The clash is “happening because Trump is transactional and Leo is ideological”, said Paul Butler, professor at Georgetown Law.
Trump “looks at the Constitution as a means to an end” and when judges rule against him, “he sees both those judges and the Constitution as obstacles to his political success”, Butler added. With values “rooted in conservative constitutional jurisprudence . . . Leo and the Federalist Society support the Constitution in a way that Trump does not”.
Asked in a television interview last month if he needed to uphold the Constitution, Trump replied: “I don’t know”.
Trump’s most unconventional moves have alienated some Federalist Society members both on and off the bench. Danielle Sassoon, a member of the Federalist Society whom Trump appointed as acting US attorney for the Southern District of New York, in February quit alongside other top prosecutors following an order from the government to drop the corruption prosecution of New York City mayor Eric Adams, a Trump ally.
Top conservative lawyers including Paul Clement, Miguel Estrada and Bill Burck have all committed to defend clients against Trump administration attacks.
Given Trump’s tendency to blow hot and cold, the schism may not last. The two sides have similar views on how the Constitution grants broad power to the president as head of the executive branch. The Supreme Court on Friday temporarily authorised the administration to scrap policies that granted legal protection to approximately 500,000 immigrants.
And Leo himself sought to smooth the waters.
“I’m very grateful for President Trump transforming the Federal Courts, and it was a privilege being involved,” he said in a statement. “There’s more work to be done, for sure, but the Federal Judiciary is better than it’s ever been in modern history.”
Still, frustration with legal setbacks may push Trump to prefer loyalists in future appointments. On Wednesday, he nominated Emil Bove, his former personal lawyer and a Justice Department official, to a federal appeals court seat.
“It will be important to watch how the splintering between Trump and Leo shapes the alignment of conservative Republican Senators on judicial appointments and more,” said Ryan Goodman, professor at the NYU School of Law.
Nearly all of Trump’s nominees — including his most controversial picks — have been confirmed by a Congress that has yet to push back against the president in a meaningful way.
Even Leo’s effusive response to the Truth Social post suggests Trump may have the upper hand. A shift to loyalist judicial appointments could erode the Federalist Society’s sway and risks backfiring if it sets precedents that may be seized by future Democratic presidents.
But if Trump’s fury towards dissenting judges deepens the split with Leo, the conservative activist may have to choose between staying true to his judicial philosophy and retaining his influence in the White House.
The Trump administration uses “online rhetoric as a way of catalysing actions by other people”, said Aziz Huq, professor at the University of Chicago Law School.
“[There are] many moments where what’s required is an overt bending of the knee, not to the Constitution, but to Trump personally.”
