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Trump lashes out at legal activist and onetime ally: “Probably hates America”

by Joe Walsh
May 29, 2025
Reading Time: 4 mins read
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Trump lashes out at legal activist and onetime ally: “Probably hates America”

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President Trump attacked the powerful conservative legal activist Leonard Leo late Thursday, calling the former Federalist Society leader who once advised the president on Supreme Court picks a “bad person” who “probably hates America.”

Mr. Trump lashed out at Leo a day after a panel of judges — including a Trump appointee — called most of his tariffs illegal. The ruling, which was paused by an appellate court, put Mr. Trump at odds with some conservative lawyers: Two of the three judges who decided the case were appointed by Republicans, and the decision came in response to a lawsuit that cited right-leaning legal theories.

The president attacked the three judges behind that ruling in a Truth Social post late Thursday, calling it a “horrible, Country threatening decision” and suggesting it was made because the judges hate him. He then turned his attention to Leo and the Federalist Society, two longstanding pillars of the conservative legal movement widely credited with helping Mr. Trump pick hundreds of federal judges — some of whom have ruled against his administration.

“I was new to Washington, and it was suggested that I use The Federalist Society as a recommending source on Judges,” Mr. Trump wrote on Truth Social late Thursday. “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 to Politico, Leo said: “I’m very grateful for President Trump transforming the Federal Courts, and it was a privilege being involved,” Leo said. “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.”

CBS News has reached out to Leo and the Federalist Society for comment.

Mr. Trump’s attacks on Leo and the Federalist Society are striking because of their years-long alliance with the president. During his 2016 campaign, Mr. Trump promised to listen to the right-leaning legal organization when making judicial picks, saying in an interview: “We’re going to have great judges, conservative, all picked by the Federalist Society.”

During Mr. Trump’s first term, Leo advised the president on his Supreme Court picks, who form a key part of the high court’s 6-3 conservative majority.

Leo spoke with Mr. Trump shortly after Justice Anthony Kennedy announced his retirement in 2018, opening up a vacancy on the court that was filled by Brett Kavanaugh, Leo told CBS News at the time. When asked how Mr. Trump decided to create a list of possible high court nominees, Leo said the president “called and asked to meet and suggested the idea of doing a list.”

Mr. Trump spoke positively about Leo in his first term. “We had a list that you worked on very hard, and others,” the president said in a 2019 event.

But on Thursday, Mr. Trump said he’s “disappointed in The Federalist Society because of the bad advice they gave me on numerous Judicial Nominations.” 

Mr. Trump also noted Leo has “left The Federalist Society to do his own ‘thing,'” possibly referring to Leo’s work with the Teneo Network, a group intended to — in Leo’s words — “crush liberal dominance” in fields other than law, from entertainment to finance.

The president has clashed with judges repeatedly in recent months, as parts of his agenda — including tariffs and immigration policy — face pushback from the federal judiciary.

In particular, tariffs could pit one of Mr. Trump’s signature economic policies against some of the legal theories championed by the conservative judicial movement. Lawsuits arguing Mr. Trump doesn’t have the power to levy sweeping global tariffs have cited the nondelegation doctrine and the major questions doctrine, two legal concepts that right-leaning members of the Supreme Court — including ones chosen by Mr. Trump — have embraced for years.

More from CBS News

Joe Walsh

Joe Walsh is a senior editor for digital politics at CBS News. Joe previously covered breaking news for Forbes and local news in Boston.

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Joe Walsh

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