Key Points – President Donald Trump publicly attacked the Federalist Society and its co-chairman Leonard Leo on Truth Social this week, calling Leo a “sleazebag” who “probably hates America.”
-This outburst followed a US Court of International Trade ruling that initially found Trump overstepped his authority on tariffs, though an appeals court later allowed them to temporarily remain.
-Trump questioned the motives of the judges and blamed the Federalist Society for its recommendations.
-Leonard Leo, a key architect of the conservative judiciary, responded by praising Trump’s judicial appointments as his most important legacy, opting not to escalate the feud.
Trump Declares War on Federalist Society & Leonard Leo Over Court Rulings
When it comes to legal philosophies, the Federalist Society is committed to the conservative legal project that has been in place for decades.
On the other hand, Donald Trump is committed to having the ability, as president, to do whatever he wants without any judicial pushback.
The two sides have often been aligned, such as when the Federalist Society recommended judges to Trump, and he appointed three conservative justices to the Supreme Court in his first term, leading to the fruition of such longtime conservative goals as the overturning of the Roe v. Wade and Chevron decisions.
On the other hand, especially in his second presidency, Trump sometimes had judges rule against him, which greatly angered him. And this week, he went off on the Federalist Society and the chairman of its board, Leonard Leo.
A Tariff Decision
Earlier this week, the U.S. Court of International Trade ruled that Trump had overstepped his bounds when imposing most of the tariffs.
However, the following day, the U.S. Court of Appeals for the Federal Circuit allowed the tariffs to temporarily remain in effect.
Trump then took to Truth Social, and rather than acknowledging that judges can sometimes have different interpretations of the law, he acted incredulous that any judge could possibly rule against what he wants.
“Where do these initial three Judges come from? How is it possible for them to have potentially done such damage to the United States of America? Is it purely a hatred of “TRUMP?” What other reason could it be?”
The president went on to blame the Federalist Society for recommending the judges that it recommended.
“I was new to Washington, and it was suggested that I use The Federalist Society as a recommending source on Judges,” Trump wrote in the Truth Social 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.”
Leo Responds
The shots at Leo were somewhat surprising, as much legal analysis in the last decade has dealt with Leo’s shadowy influence, the ways that Trump’s first term moved the federal judiciary to the right, and the implications for the country. Leo has set up a network that identifies young conservative talent and tries to funnel such people into the judiciary.
There had been little indication, before Thursday, that Trump and Leo were at odds. In an interview last November, after Trump won the election, Leo declared that “I want to crush liberal dominance.” There were later protests at Leo’s home in Maine.
An Axios story last fall stated that Leo, who had “an estimated $1 billion at his disposal,” was threatening to withhold funding from some conservative groups unless they found ways to “weaponize” their ideas.
After Trump’s Truth Social post, Leo issued a statement, as reported by Fox News, in which he opted not to fire back.
“I’m very grateful for President Trump transforming the federal courts, and it was a privilege being involved,” Leo said in the statement. “There’s more work to be done, for sure, but the federal judiciary is better than it’s ever been in modern history, and that will be President Trump’s most important legacy.”
The Barrett Question
Justice Amy Coney Barrett, nominated by Trump late in his first term following the passing of Justice Ruth Bader Ginsburg, has come in for some criticism from the right, as she has sometimes gone against the Trump Administration’s position, including in some immigration decisions.
Leo, earlier this spring, defended her, which may have been the start of the disappointment with him.
“I wouldn’t characterize his appointment of her as being a DEI hire,” Leo told The Hill in April. “She’s so well credentialed, she’s so demonstrably conservative in her outlook on the role of the courts, that I just think that kind of mischaracterizes it.”
About the Author:
Stephen Silver is an award-winning journalist, essayist and film critic, and contributor to the Philadelphia Inquirer, the Jewish Telegraphic Agency, Broad Street Review and Splice Today. The co-founder of the Philadelphia Film Critics Circle, Stephen lives in suburban Philadelphia with his wife and two sons. For over a decade, Stephen has authored thousands of articles that focus on politics, technology, and the economy. Follow him on X (formerly Twitter) at @StephenSilver, and subscribe to his Substack newsletter
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