During President Trump’s first term, he effectively outsourced the task of picking judges to lawyers closely associated with the Federalist Society, a 43-year-old conservative legal group, and Leonard Leo, then its executive vice president.
But in his second term, after some of those judges failed to rule in his favor in cases testing the legality of his policy moves, Mr. Trump has lashed out against the organization. In a lengthy social media post in May, he called Mr. Leo a “sleazebag” who “openly brags how he controls Judges.” The Federalist Society, he said, had given him “bad advice.”
Considering the crowd that assembled earlier this month in Washington for the Federalist Society’s annual lawyers’ convention — including many close allies of Mr. Trump — it was clear that the organization still commands influence.
Dozens of federal judges from across the country attended the event at the Washington Hilton. Justices Brett M. Kavanaugh and Amy Coney Barrett of the Supreme Court spoke at the gala dinner and a third justice, Samuel A. Alito Jr., sat among the crowd of 2,300.
What was less clear was if the organization was ready to fully embrace the hyperaggressive legal views of the president who had empowered it like never before.
From the stage, Todd Blanche, the deputy attorney general, and Chad Mizelle, who recently stepped down from another top Justice Department position, delivered stem-winding remarks slamming judges who had stood in Mr. Trump’s way.
But the convention’s panels also offered a platform to speakers who questioned key administration policies, including attempts to curtail diversity, equity and inclusion programs and deploy the National Guard in U.S. cities.
In an interview, Mr. Leo said the Federalist Society was “not monolithic” but rather a “crucible and a proving ground” where conservatives could “work out their differences, or they make their points and try to persuade other people of what their positions are.”
Even after his complaint about Mr. Leo’s influence over first-term picks, Mr. Trump has continued to use the Federalist Society’s pipeline of judicial talent. The size of the group’s network means that most qualified, Republican-friendly judicial nominees will have some ties to it. Indeed, out of six nominees to the appellate courts that Mr. Trump has chosen in his second term, five have spoken at a society event, according to its website.
But for a society that claims the Constitution as the uniting force for its varied membership, some longtime allies have warned Mr. Trump’s second term poses an unusual challenge. Actions like killing people suspected of trafficking drugs at sea, ordering up investigations of his political opponents and excoriating judges who rule against him, they say, violate both the letter and spirit of America’s founding document.
“There’s a real tension, from a rule-of-law perspective, between some members of the Federalist Society and the Trump administration,” said Edward Whelan, an attorney who has spoken at dozens of the society’s events, and clerked for Justice Antonin Scalia.
“Good judges will make the hard calls they’re obligated to make without worrying what people will say about them. MAGA-oriented voices say that they want fearless judges — but many of them seem really to want judges who will do Trump’s bidding,” he said.
The Original Originalists
The Federalist Society was founded in 1982 by law students from Yale, Harvard and the University of Chicago. Back then, right-leaning students attending elite law schools saw themselves as an embattled minority whose ideas could not get a fair hearing on campuses entranced by the progressive jurisprudence popular in the decades after World War II.
The group was quickly championed by leading conservative thinkers, including Mr. Scalia, the future Supreme Court justice. By the mid-1980s, it had grown to dozens of campus chapters.
As it gained influence, some liberal critics began painting the Federalist Society as a right-wing effort to remake the judiciary. But the group was careful to set limits on its tactics, if not on its ambitions. It did not take positions on issues or make arguments in court. Its power was instead informal, a function of its far-reaching network.
The alliance between the Federalist Society and Mr. Trump started during his first White House run. Over the next few years, Mr. Leo, then the group’s executive vice president, would begin carving out an influential role in Republican politics outside the society, one that would eventually encompass raising millions of dollars for other conservative groups and helping lead a for-profit media relations firm.
Mr. Trump, who needed to reassure traditional conservatives who were still getting to know him, welcomed the organization’s network into his campaign. In 2016, he met with Mr. Leo and Donald F. McGahn II, a longtime society member and a campaign lawyer who would become his White House counsel, to discuss a list of potential Supreme Court nominees. In a statement, a spokesman for the society said that any influence that the group might have exercised over Mr. Trump’s judicial picks came from individual members, not from the society as a whole. But Mr. Trump sometimes ignored that distinction. “We’re going to have great judges, conservative, all picked by Federalist Society,” Mr. Trump said in a June 2016 interview with Breitbart.
In February 2017, when Mr. Trump held a press event to tout Neil M. Gorsuch as his first Supreme Court pick, Mr. Leo was there.
Later that year, Mr. McGahn, who was responsible for managing Mr. Trump’s judicial nominees, poked fun at the claim that Mr. Trump had outsourced the process. “I’ve been a member of the Federalist Society since law school — still am,” he said in a lecture at the society’s annual convention. “So, frankly, it seems like it’s been insourced.”
But as Mr. Trump’s first term drew to a close, his relationship with Mr. Leo soured. In 2020, Mr. Trump publicly berated him at Mar-a-Lago over the Justice Department’s investigation into ties between Mr. Trump’s campaign and Russia, claiming Mr. Leo had recommended the deputy attorney general, Rod J. Rosenstein, who had appointed a special counsel. And Mr. Leo did little to marshal conservative support for Mr. Trump’s efforts to overturn his defeat at the polls by Joseph R. Biden Jr.
Mike Davis, the founder of the Article III Project, a legal nonprofit that also espouses originalism but is more closely aligned with the MAGA movement, said too many of the Federalist Society’s leaders were “missing in action” during the Biden years, when Mr. Trump faced criminal investigations and a lengthy trial. “Some of those Fed Soc leaders even cheered on the lawfare,” he said. Mr. Trump’s falling out with Mr. Leo cast some doubt on whether Mr. Leo’s network would continue to wield as much influence in the second term.
Asked if the group had any current role in selecting judges, a White House spokeswoman, Abigail Jackson, said Mr. Trump relied on his advisers and the Justice Department to identify and vet candidates.
“Other individuals and groups are always free to share their views, but the president is the ultimate decision maker,” she said.
The crowd at an Article III Project reception last month, blocks from the White House, was one indication that the Federalist Society now has some competition. Inside the private party at Café Fiorello were Kash Patel, the F.B.I. director; Jeanine Pirro, the U.S. attorney for Washington; Gen. Michael T. Flynn, a former Trump national security adviser and later, pardon recipient; as well as Mr. Blanche and Mr. Mizelle.
Also present was the White House counsel, David Warrington, whose office manages the judicial selection process.
“It’s a War, Man”
Today, the Federalist Society still considers itself to be a “big tent” debating society, one that welcomes a range of conservative views — including those who have adopted Mr. Trump’s criticism of a judiciary filled with society members.
“It’s a war, man,” Mr. Blanche told the crowd, speaking of Justice Department efforts to appeal unfavorable rulings. He criticized “activist judges” who he said were “more political or as political as the most liberal governor or D.A.”
Mr. Mizelle, speaking on a panel, told a story about a call his father had made to the local Humane Society about a stray cat that was wandering through his yard. Mr. Mizelle compared judges to the felines. “I’m from Mississippi,” he recalled his father saying. “We know how to deal with stray cats.”
This was met with a mix of mild chuckles and stunned silence from the audience.
Mr. Mizelle, who is married to a Trump-appointed federal judge, explained minutes later that his proposed solution was to impeach judges who blocked administration policies, something that Chief Justice John G. Roberts Jr. has said would be improper.
Mr. Mizelle did not respond to a request for comment. A spokesperson for the Justice Department said that the department would “continue to follow the Constitution” and “defend its lawful authorities.”
While administration officials were comfortable delivering broad-bore criticisms of the judiciary, the judges at the convention skirted the president whose agenda had provoked lawsuits that were occupying so much bandwidth at their courthouses. In an evening lecture, Judge Andrew Oldham, a Trump nominee from the U.S. Court of Appeals for the Fifth Circuit, pondered whether there should be some limit to the Federalist Society’s “big tent” approach, even as he gave what sounded like a chest-thumping affirmation of Trump-era conservatism.
He praised the murdered conservative activist Charlie Kirk and threw shade at the Biden-era pandemic czar Dr. Anthony Fauci. And he tallied conservative Supreme Court wins on issues like abortion and gun control.
“Textualism won. Originalism won,” he said, declaring victory for the Federalist Society’s two guiding legal philosophies, which ask that judges focus on the exact wording of laws and the meaning of the Constitution at the time of the nation’s founding.
But at least one judge in the audience felt it was too soon for Judge Oldham to proclaim that the conservative legal movement had won.
Before the speech was done, Judge William H. Pryor Jr., the 63-year-old chief judge of the U.S. Court of Appeals for the 11th Circuit, texted Judge Oldham and other members of the conservative appellate bench a bespoke meme. It was the famous photo of President George W. Bush in 2003, standing on an aircraft carrier in front of a “Mission Accomplished” banner, announcing victory in a war that would drag on for years. In place of Mr. Bush’s head was Judge Oldham’s — a barbed inside joke suggesting that the fight for originalism and textualism was far from over.
In an interview a few days after the convention, Judge Pryor said he did not intend for the meme, which was described to the The Times by a recipient who asked not to be identified, to become public.
“That was really meant to be a private joke between me and Judge Oldham, as friends,” he said. He declined to comment further.
Even as originalists gained power due in large part to Mr. Trump’s nominations, some at the convention felt that fidelity to constitutional principles now required a break with the president’s agenda.
In attendance was Ilya Somin, one of the lawyers for the private businesses in the Supreme Court case challenging Mr. Trump’s tariffs, who praised judges who have ruled against Mr. Trump. Referencing Mr. Mizelle’s judges-as-cats analogy, Mr. Somin said cats “can be very useful in catching rats,” which he characterized as the administration’s “massive abuses of power in many areas.”
In the interview, Mr. Leo took a more conciliatory tone toward Mr. Trump, saying his judicial picks have “ushered in a series of generational wins” that “conservatives never would have imagined.” But he suggested the president should take at least some of his courtroom losses in stride.
“The conservative movement owes the president a debt of gratitude for what he did,” Mr. Leo said. “That doesn’t necessarily mean that he is going to win on every issue the way he wants to win.”
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