Federalist Society co-chair Leonard Leo speaks to the media at Trump Tower, in New York Nov. 16, 2016. The Federalist Society has recommended people for judicial appointments, the most prominent of them Supreme Court justices Neil Gorsuch, Amy Coney Barrett and Brett Kavanaugh, all of whom Donald Trump appointed to the court during his first term as president. (AP/Carolyn Kaster)
by Allison Prang
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President Donald Trump lambasted prominent conservative mega donor and Catholic, Leonard Leo, calling him a "sleazebag" and accusing Leo's Federalist Society of giving him “bad advice” on some judicial nominations.
The attack marks a notable and unexpected shift in the president's relationship with Leo. Trump particularly turned to Leo, along with the Federalist Society, a conservative and libertarian organization focused on the legal system that Leo co-chairs, for recommendations on judicial appointments. The most prominent of those were Supreme Court justices Neil Gorsuch, Amy Coney Barrett and Brett Kavanaugh, all of whom Trump appointed to the court during his first term in office.
Trump, posting on his social media platform Truth Social on May 29, said he relied on the Federalist Society for recommendations for judges before realizing the organization was led by Leo, who Trump said is "a bad person who, in his own way, probably hates America, and obviously has his own separate ambitions."
"I am so disappointed in The Federalist Society because of the bad advice they gave me on numerous Judicial Nominations," Trump said in his post. "This is something that cannot be forgotten! With all of that being said, I am very proud of many of our picks, but very disappointed in others."
Leo, in response to Trump's remarks, touted Trump’s record of appointing judges.
"I'm very grateful for President Trump transforming the Federal Courts, and it was a privilege being involved," Leo said in a statement provided by a spokesperson. "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."
Judge Amy Coney Barrett holds her hand on the Bible as she is sworn in as an associate justice of the U.S. Supreme Court by Supreme Court Justice Clarence Thomas at the White House in Washington Oct. 26, 2020. (OSV News/Reuters/Tom Brenner)
Trump's comments disparaging some of his judicial nominees come during what has been a legally explosive few months for his second administration, with many of its actions being challenged in court. In his social media post, Trump specifically called out a ruling this week from the U.S. Court of International Trade that said his tariffs went beyond a president’s emergency powers. That ruling was quickly paused by the U.S. Court of Appeals for the Federal Circuit the same day.
"How is it possible for them to have potentially done such damage to the United States of America?” Trump said in his post, referring to judges on the U.S. Court of International Trade. Trump later invoked the Supreme Court in the same post, saying he hopes the justices will side with him on tariffs.
"Hopefully, the Supreme Court will reverse this horrible, Country threatening decision, QUICKLY and DECISIVELY," Trump said.
The Supreme Court, the majority of whose justices lean conservative, has sided with the Trump administration on a number of issues, including ruling it could fire leaders of independent agencies without giving a reason. It's ruled against the administration on others, however, like when it ruled that the administration needed to try to bring back Kilmar Abrego Garcia, a Maryland man wrongly deported to an El Salvadoran prison.
In an interview with NBC's "Meet the Press" in early May, Trump said he had "tremendous respect for the Supreme Court" but also said that justices "change," noting "it's unbelievable how that happens."
One of those justices is another Leo recommendation: Barrett, whose votes have not predictably sided with the president. Barrett, who Trump appointed to the Supreme Court in 2020, has taken heat from some Trump fans for not voting with her conservative counterparts on the bench.
Barrett also joined Chief Justice John Roberts in March in siding with the court's three liberal justices to force the administration to disburse $2 billion in foreign aid for work that had already been completed.
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Leo's influence on the Supreme Court goes beyond the three justices appointed to the bench during Trump’s first term. Leo also pushed for Roberts’ nomination to the court as well as fellow conservative Justice Samuel Alito. Leo also helped Justice Clarence Thomas in his confirmation hearings.
While Leo still co-chairs the Federalist Society, he also chairs CRC Advisors, a public affairs firm whose client roster has included several prominent Catholic groups, including the U.S. Conference of Catholic Bishops. Leo has also been a big fundraiser for Catholic University of America in D.C., helping the school raise millions of dollars in donations in recent years.
Leo has also used some of his money to buy a church. In 2023, he bought St. Ignatius of Loyola Catholic Church in Maine's Northeast Harbor from the Roman Catholic bishop of Portland for $2.65 million, a purchase he made using a nonprofit organization called the Sacred Spaces Foundation which listed Leo as its sole member and president, according to the Associated Press.
Leo regularly attends nearby Holy Redeemer in Bar Harbor, Maine, which has pushed away some parishioners, the AP reported. In response to their leaving, Leo wrote that he was "thankful for every person who takes the time to come to Holy Redeemer," the wire service said.
