NEW YORK – Leonard Leo, a conservative legal activist, played a pivotal role in reshaping the federal judiciary during President Donald Trump’s first term. He was a key advisor to Trump on Supreme Court nominations and is widely recognized for crafting the conservative majority that led to the overturning of Roe v. Wade.
However, Trump recently criticized Leo, attributing his discontent to Leo’s past recommendations, which led to the appointment of judges who are now hindering Trump’s initiatives. Trump described Leo, the former head of the conservative Federalist Society, as a “real ‘sleazebag’” and a “bad person who likely harbors disdain for America.”
Trump’s outrage followed a decision by a three-judge panel at the U.S. Court of International Trade that struck down his expansive tariffs, concluding that he had exceeded his legal authority by using the 1977 International Emergency Economic Powers Act to justify a national emergency and impose tariffs on imports from nearly every country globally.
While an appeals court soon intervened and allowed the administration to continue collecting the tariffs while the legal fight plays out, the decision — and Trump’s fury at Leo — underscored the extent to which the judiciary is serving as a rare check on Trump’s power as he pushes the bounds of executive authority. The judiciary has intervened as he has ordered mass deportations, deep cuts to university funding and the firing of federal workers en masse.
Trump’s words reflect his broad frustrations with the judiciary, including members of the Supreme Court he appointed on Leo’s recommendation, who have allowed some of his more controversial efforts to move forward, but blocked others.
Trump’s rhetoric also appeared to be a tactic to shift blame for setbacks to his agenda — this time notably pointing the finger at a person who once helped Trump build credibility with conservative voters. But it’s unclear what — if anything — Leo had to do with the tariff decision.
Leo said that neither he nor the Federalist Society was involved in shaping appointments to the trade court. He offered only praise for Trump.
“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.”
Trump’s attacks
Trump’s fury came via Truth Social after the court tried to halt the central plank of the president’s economic agenda: sweeping tariffs that have rattled global financial markets, dismayed longtime trading partners, and prompted warnings about higher prices and inflation.
In response, Trump issued a lengthy and angry missive criticizing the judges behind the decision, accusing them of “destroying America” and saying he hoped the Supreme Court would quickly reverse “this horrible, Country threatening decision.”
Trump then referred to his first term as president, saying he “was new to Washington, and it was suggested that I use The Federalist Society as a recommending source on Judges. 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.”
“I am so disappointed in The Federalist Society because of the bad advice they gave me on numerous Judicial Nominations,” he wrote. “This is something that cannot be forgotten!” He added: ”Backroom ‘hustlers’ must not be allowed to destroy our Nation!”
Some conservatives, including legal scholars, have been among those pushing back against Trump’s trade wars, arguing the Constitution makes clear the power of the purse belongs to Congress, not the president.
In April, the New Civil Liberties Alliance, a nonprofit group that Bloomberg Law reported is affiliated with Leo and Charles Koch, filed a separate lawsuit challenging Trump’s tariffs on Chinese imports, also accusing him of acting in violation of the International Emergency Economic Powers Act.
That move earned the ire of prominent Trump backers like Laura Loomer, who accused both Leo and the Federalist Society of working to undermine the president.
The panel Trump assailed included judges appointed by Presidents Barack Obama and Ronald Reagan, as well as Timothy Reif, whom Trump nominated to the trade court during his first term. Reif, a Democrat, had previously worked for the U.S. Trade Representative in both the Obama and Trump administrations.
In a questionnaire submitted to the Senate Judiciary Committee as part of his confirmation process, Reif described working on a long list of Democratic campaigns. He volunteered on Edward Kennedy’s presidential campaign in 1980, driving the press van in Kennedy’s motorcade. He served as press secretary for John Lindsay’s Senate campaign in 1980 and volunteered for New Jersey Rep. Rush Holt’s reelection effort in 2000, when his responsibilities included “driving and accompanying candidate’s mother to campaign events.”
He also volunteered for John Kerry in 2024 and Obama in 2008, and donated small amounts years ago to the Clintons and the Democratic Congressional Campaign Committee.
He appears to have participated in one Federalist Society-affiliated event: a panel on international trade in 2011 held by the Georgetown Law Student Chapter.
The Federalist Society and Reif did not respond to requests for comment Friday.
The White House did not respond to questions about why Trump blamed Leo and the Federalist Society for the decision, but Taylor Rogers, a White House spokesperson, doubled down, calling Leo “a bad person who cares more about his personal ambitions than our country.”
“These judges must ditch their corrupt allegiance to Leonard and do the right thing for the American people before they completely destroy the credibility of our judicial branch,” she said.
Who is Leonard Leo?
Leo is not a household name, but few people have done more to advance conservative legal causes in the U.S. via a sprawling network of conservative groups.
Decades ago, he began to execute a plan to build a pipeline for conservative talent, working to identify, support and promote law school students and lawyers who shared his originalist view of the Constitution, and helping them reach the nation’s most powerful courts. Such efforts have reshaped the courts and Republican politics, culminating in Trump’s first term with the appointment of three conservative Supreme Court justices. Leo’s work also has prompted protests outside his home.
The Federalist Society got its start on college campuses when Reagan was president. It was conceived as a way to counter what its members saw as liberal domination of the nation’s law-school faculties.
During his 2016 campaign, as Trump worked to win over social conservatives wary of electing a thrice-married New York businessman, he promised that the Federalist Society would oversee his judicial nominations, assuring their non-liberal bona fides.
“We’re going to have great judges, conservative, all picked by the Federalist Society,” Trump told Breitbart News radio.
And indeed, all three of the Supreme Court Justices Trump went on to nominate had appeared on a list famously compiled by Leo, who took a leave of absence as executive vice president of the society to serve as an outside adviser in the selection process.
Leo has since stepped back from the Federalist Society and is now working to extend his reach beyond the courts with the Teneo Network, which he has described as an effort to “crush liberal dominance” and create pipelines of conservative talent “in all sectors of American life,” including Hollywood, entertainment, business and finance.
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