Leonard Leo, co-chariman of the Federalist Society board of directors, speaks at the University of Cambridge in England on March 11, 2025.
Credit - Nordin Catic/Getty Images for The Cambridge Union "A real 'sleazebag'" and "bad person." Someone who "probably hates America." The latest target of Donald Trump's insults, however, is the very same whom he once credited with what he would later call "one of the greatest achievements" of his presidency. "We're going to have great judges, conservative, all picked by the Federalist Society," Trump promised during his first campaign in 2016. It was the result of a meeting in March 2016 with Leonard Leo, then the executive vice president of the Federalist Society, a conservative organization that advocates for legaloriginalism. True to his promise, Trump would go on to consult Leo for judicial nominations, including his three Supreme Court picks. Read More:Inside Trump's Plan to Dramatically Reshape U.S. Courts[From 2018] "What we're doing with the courts, I think, is going to go down as one of the greatest achievements," Trump said during his first term. But on Thursday, Trump had changed his tune. "I was new to Washington, and it was suggested that I use The Federalist Society as a recommending source on Judges," hepostedon his social media platform Truth Social. "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. He openly brags how he controls Judges, and even Justices of the United States Supreme Court—I hope that is not so, and don't believe it is! In any event, Leo left The Federalist Society to do his own 'thing.' I am so disappointed in The Federalist Society because of the bad advice they gave me on numerous Judicial Nominations. 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." Trump's rant came after a federal three-judge panelruledthat he didn't have the authority to impose most of the tariffs he'd announced so far in his second term, a key part of his economic agenda and promise to bringmanufacturing jobsback to America. Leo, in response, offered a less combative response. "I'm very grateful for President Trump transforming the Federal Courts, and it was a privilege being involved," he said ina 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." Here's what to know about Leo and the Federalist Society—and their falling out with Trump. Founded in 1982by a group of law school studentsas a pro-originalism organization for law students, the Federalist Society for Law and Public Policy Studies has been describedas"the single most influential advocacy organization in Washington." The organization—which counts over 90,000 lawyers, law students, scholars, and others among its members—describes itselfas "a group of conservatives and libertarians interested in the current state of the legal order." But that puts it mildly: the organization, especially under Leo's leadership, has been credited with creating a "pipeline," utilizing its vast network, for conservative law students to make their way into positions of influence—ideally, all the way up to the Supreme Court. A2023 studyshowed that, in the current confirmation process, a judicial nominee's affiliation with the Federalist Society increased the probability of a successful Senate confirmation by around 20%. In 2021, Sen. Sheldon Whitehouse (D, R.I.)flaggedthat 86% of Trump's Supreme Court or appellate court nominees were or are members of the group. Six of the nine sitting Supreme Court justices—Chief Justice John Roberts, Clarence Thomas, Samuel Alito, Neil Gorsuch, Brett Kavanaugh, and Amy Coney Barrett—are linked to the Federalist Society, particularly through Leo. ProPublicadescribed the Federalist Society as part of "a machine that remade the American legal system." It described Leo as the man who "built" that machine. The conservative legal activist joined the Federalist Society in 1989, when he started a student chapter of the organization while studying law in Cornell. For many years, he served as executive vice president of the organization until he stepped back in 2020, though he remains co-chair of its board of directors. Leo's most significant and long-lasting impact is probably his work related to the makeup of the Supreme Court. In 1990, before he even began officially working for the Federalist Society, as a 25-year-old clerk for a U.S. Court of Appeals judge in Washington, he met then-appellate judge Thomas, whom he befriended and helped through his Supreme Court confirmation in 1991. During the George W. Bush Administration, Leo organized efforts to lobby for the nominations of Roberts and Alito. And during Trump's first term, Gorsuch, Kavanaugh, and Coney Barrett were all selected from a list reportedly "personally curated" by Leo. But the Federalist Society isn't the only powerful organization Leo has championed. "The network of increasingly influential conservative groups that Leonard A. Leo has helped to create and shape is not easily defined or quantified," theNew York Timesreportedin 2022. Many of those groups have funding sources that have been difficult to trace and have funnelled billions of dollars to conservative causes,including groupsthat had been preparing for Trump's second term. Politicoreported that the relationship between Leo and Trump became strained when the three conservative justices Trump appointed to the Supreme Court on Leo's advice "did not intervene to keep Trump in office after he lost the 2020 presidential election." Leo, however, has generally refrained from publicly criticizing Trump—and the Federalist Society has reportedly appeared "ambivalent" about Trump's second-term Administration so far, compared to itsenthusiasmduring his first—though Trump's tariffs appear to be a major breaking point. In April, the New Civil Liberties Alliance, a group affiliated with Leo,mounteda legal challenge against levies imposed on Chinese imports,arguingthat the President misapplied the International Emergency Economic Powers Act (IEEPA) cited to order the tariffs. While that case remains ongoing, the U.S. Court of International Trade found that Trump misused the same presidential authority in aruling this weekon separate tariff cases. Trump'ssocial-media outburstagainst the judges on that court and against Leo and the Federalist Society came as his Administration has increasingly challenged the authority of the judicial branch torein in his powers. Still, the President may be relying on Leo's greatest accomplishment to ultimately push his agenda through. "Hopefully," Trump added in his social media post, "the Supreme Court will reverse this horrible, Country threatening decision, QUICKLY and DECISIVELY." Contact usatletters@time.com.
