President Donald Trump is escalating tensions with the conservative legal establishment that once shaped his judicial legacy. In a blistering Truth Social post Thursday night, Trump denounced a court decision blocking his tariff plans—and took direct aim at Leonard Leo, the longtime Federalist Society executive behind many of his first-term judicial appointments.
The U.S. Court of International Trade had halted key portions of Trump’s proposed tariffs, a decision that was temporarily lifted on appeal, only for a separate court to issue a conflicting injunction set to take effect in two weeks. Calling the rulings “country-threatening,” Trump urged the Supreme Court to intervene and accused “backroom hustlers” of undermining his agenda.
Among them, he named Leo—once a trusted advisor—labeling him a “sleazebag” driven by self-interest. “I was new to Washington,” Trump wrote, noting that he relied on the Federalist Society’s vetting process for judges early in his presidency. “I am very proud of many of our picks, but very disappointed in others.”
The Hill noted that Leo played a pivotal role in assembling the list of judicial candidates Trump used in 2016, which led to the appointments of Justices Gorsuch, Kavanaugh, and Barrett—cementing a 6-3 conservative majority on the Supreme Court. While many conservatives hail that legacy, Trump has grown increasingly critical after recent rulings—including the trade court decision—came from judges he helped appoint.
Judge Timothy Reif, a Trump appointee and registered Democrat, sat on the panel that blocked the tariffs. Trump used the moment to cast doubt on the Federalist Society’s influence, suggesting their guidance had produced mixed results.
Leo, for his part, responded graciously, calling his role in shaping the judiciary under Trump a “privilege.” But his influence appears to be fading. Trump has bypassed Federalist channels in his second term, instead relying on loyalists—including former defense attorney Emil Bove, now a top figure in the Justice Department—for new judicial nominees.
