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“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

legal originalism. Advertisement Advertisement True to his promise, Trump would go on to consult Leo for judicial nominations, including his three Supreme Court picks. “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,” he posted on 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 panel ruled that 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 bring manufacturing jobs back 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 in a 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. WHAT IS THE FEDERALIST SOCIETY?  Founded in 1982 by a group of law school students as a pro-originalism organization for law students, the

Federalist Society for Law and Public Policy Studies has been described as “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 itself as “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. A 2023 study showed 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.) flagged that 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. WHO IS LEONARD LEO? ProPublica described 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,” the _New York Times_ reported in 2022. Many of those

groups have funding sources that have been difficult to trace and have funnelled billions of dollars to conservative causes, including groups that had been preparing for Trump’s second term.

WHY DID TRUMP SOUR ON LEONARD LEO? Politico reported 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 its enthusiasm during 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, mounted a legal challenge against levies imposed on Chinese imports, arguing that 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 a ruling this week on separate tariff cases. Trump’s social-media outburst against 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 to rein 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.”