From friends to foes: How Trump turned on the Federalist Society

The dramatic consequences of Donald Trump’s fall captured the world’s attention last week. But at the same time, thanks to an unflattering nickname, the president also widened the rift between his royal court (MAGA) and the conservative legal movement, whose judges and lawyers have played a crucial role in shifting the American judiciary to the right.

The term “corrupt” was used by Trump in a lengthy attack on Truth Social, his social media platform. The mockery targeted the Federalist Society, a powerful conservative legal organization, and Leonard Leo, a lawyer associated with the group who has grown in recent years to become one of the most influential right-wing policymakers in the United States.

In his message, Trump stated that during his first term, “it was suggested to me that I use the Federalist Society as a source of recommendations for judges. I did so publicly and freely, but I later realized that it was controlled by a veritable “scumbag” named Leonard Leo, a odious individual who probably hates America in his own way and clearly harbors his own ambitions. He openly boasts of his control over the judges, even those on the United States Supreme Court—I hope not, I don’t think so!”

Trump is still under the judicial branch’s injunction. His outbursts of anger won’t change that.

Founded in 1982, the Federalist Society is a major player in the conservative movement. Many conservative lawyers, judges, law students, and legal writers are members of the group, attend its events, or are active in its inner circle. Republican presidents use its recommendations to select judges to fill vacancies.

In the days since Trump’s “social truth” speech, conservative legal figures, primarily in Washington, D.C., but also in law schools and judges’ chambers across the country, are wondering what this discord portends. Is this a typical Trumpian temper tantrum, destined to fade away? Or is it a sign of a broader divide, where even the notoriously conservative Federal Conservative Society isn’t right-wing enough—or fanatically loyal enough—to satisfy Trump?

“I don’t think this is going away,” said Stuart Gerson, a conservative lawyer and former acting U.S. attorney general. “Because this isn’t an event. This is about… he thinks judges are his judges, that they’re there to defend his policies, not the oath they take [to the Constitution].”

In recent months, Trump has suffered repeated setbacks over court rulings by federal judges. His anger has been particularly acute when the judges were appointed by him or other Republican presidents. For example, the MAGA world turned against Amy Coney Barrett after the Supreme Court Justice voted against Trump in several key cases.

The immediate trigger for Trump’s recent anger was the U.S. Court of International Trade’s ruling against his drastic tariffs on foreign goods. In this case, his anger appears less directed at the judges than at the filing of a brief by a group of conservative lawyers and academics, including one of the Federalist Society’s board chairs, challenging his tariffs. Trump is also likely aware that the New Civil Liberties Alliance (NCLA), an anti-regulation, pro-free-market legal group affiliated with Liu and billionaire Charles Koch, has filed a separate lawsuit to block the tariffs.

John Vecchione, a lawyer at the NCLA, noted that the Federalist Society is a broad organization of conservative legal scholars of various persuasions and factions, including free-market advocates and libertarians who do not share Trump’s economic nationalism. Members often disagree or find themselves on opposing sides of a case. Last February, the association’s chief federal prosecutor, Danielle Sassoon, resigned after claiming the Trump administration had tried to force her to drop a case.

Vecchione said the “real question” was what the hard-line MAGA lawyers closest to Trump are telling him.

“Are they trying to create a new organization? Or are they trying to replicate the Federalist Society’s example with the House Republican caucus… where no one wants to oppose Trump on anything?” He added, “I think some in Trump’s inner circle feel that any advocacy organization should do his bidding.”

A newer legal organization, the Article III Project (A3P), appears to have caught Trump’s attention during his second term. Founded by Trump attorney Mike Davis, the organization appears to position itself as a MAGA alternative to the Federalist Society. The A3P claims on its website to have “contributed to the confirmation” of three Supreme Court justices, 55 federal circuit judges, and 13 federal appellate judges.

Davis recently claimed in The Hill that the Federalist Society had “abandoned” Trump during his various legal battles. He added, “Not only did they abandon him, but many of the leaders of the Federalist Society participated in and fueled the legal battle.”

Although Liu was a “close ally” of Trump during his first term, the Wall Street Journal reported that Trump and Liu “have not spoken in five years.”

Liu responded tactfully to Trump’s harsh attacks. In a brief statement, he said he was “deeply grateful to President Trump for transforming the federal courts, and it was a pleasure to be a part of it,” adding that restructuring the federal judiciary would be “President Trump’s most important legacy.”

However, a lengthy article published Tuesday in the Wall Street Journal, titled “This Conservative Is Doing Fine, Thank You, After Trump Abandoned Him,” argued that Leo was “unhindered by the pressures of reelection or a reliance on outside money” and that he was “one of the few conservatives who, after being excluded from Trump’s inner circle, remains free to pursue his own vision of what will make America great again.” In 2021, a Chicago billionaire donated $1.6 billion to Leo, reportedly the largest single donation in U.S. history. As a result, Leo wields almost unprecedented influence when it comes to illicit money.

The article also points out that Leo is now primarily focused on the entertainment industry, where he finances big-budget TV series and films that embody conservative values.

Vecchione believes that Trump’s tendency to surround himself with sycophants and loyalists will work against him.

“If you have a lawyer who only tells you what you want and only does what you ask, you’re not a good lawyer,” Vecchione said. “That’s not a good way to recruit lawyers. It’s also not a good way to recruit judges.”