Last week, Donald Trump turned his fire on the Federalist Society, a powerful conservative advocacy group, and its co-founder Leonard Leo, a key adviser to Trump on judicial nominations during his first term. In a post on Truth Social, Trump called Leo a “sleazebag” and blamed the Federalist Society for “the bad advice they gave me on numerous Judicial Nominations.”
The impetus for the post was a ruling by a three-judge panel of the U.S. Court of International Trade holding that he did not have legal authority for his most sweeping tariffs (an appeals court paused the ruling the following day). When something goes wrong for Trump, he always looks for a scapegoat — and his political allies aren’t immune to such treatment.
For Trump, the conservatives’ failure to help him stay in the White House would be seen as a betrayal.
However, in the Federalist Society and Leo, Trump may have chosen the wrong targets. It is self-destructive to throw them under the bus when they have deep and continuing ties to members of the Supreme Court’s conservative majority, and when their political operation was crucial to Trump’s judicial nominations in his first term.
As Politico reports, “Trump’s relationship with [Leo] is known to have grown strained” after the fiasco of Trump’s 2020 election denialism and coup attempt. The president was sorely disappointed that the Supreme Court, including the three justices he appointed in his first term, did not do what it had done 20 years earlier when it, in effect, threw the election to George W. Bush.
Both the Federalist Society and Leo had played key roles in helping the president choose those three nominees: Justices Neil Gorsuch, Brett Kavanaugh and Amy Coney Barrett. As NPR reported in 2022, all three were on a list of potential justices that Trump shared during the 2016 campaign — “A list that was personally curated by Leo.” Justices Clarence Thomas and Samuel Alito are also close to Leo, who played a key role in securing their nominations and confirmation. Leo has become, as former Trump adviser Kellyanne Conway told ProPublica, a “den mother” to the justices, helping “take care of the judges even after they had made it to the highest court in the country.”
For Trump, for whom every action is transactional, the conservatives’ failure to help him stay in the White House would be seen as a betrayal — not just by the justices but by their patron. However, Politico reports that “despite the falling out between Trump and Leo, many legal conservatives said in recent months that they expected him to remain influential in the choices Trump makes for judicial nominations in his second term.”
This week’s ruling, however, seems to have changed that. Already, a group Leo helped funded, the New Civil Liberties Alliance, had challenged Trump’s tariffs on Chinese imports, raising the same claims of executive overreach that the trade court accepted Wednesday. And one of the three judges on the trade court who made that decision, Judge Timothy Reif, was appointed by Trump during his first term.
It is not clear what, if any, role either the Federalist Society or Leo played in Reif’s elevation to the bench. But it is clear that during his first term, Trump credited both of them for helping him transform the federal judiciary. Leo had laid the groundwork for that transformation, as ProPublica reported in 2023:
Decades ago, he’d realized it was not enough to have a majority of Supreme Court justices. To undo landmark rulings like Roe, his movement would need to make sure the court heard the right cases brought by the right people and heard by the right lower court judges. Leo began building a machine to do just that.
Besides pampering members of the Supreme Court, he placed Federalist Society members in “clerkships, judgeships and jobs” not only at the federal level but throughout the states as well.
That, it seems, was then. Now, says Trump, Leo is “a bad person who, in his own way, probably hates America.” The president’s changing mood doesn’t change the fact that, as Time reporter Chad de Guzman explains, “the President may be relying on Leo’s greatest accomplishment to ultimately push his agenda through.”
Already, however, Republican-appointed judges are ruling against Trump’s second administration nearly as often as Democratic-appointed judges. And while there were far fewer vacant judgeships at the start of Trump’s second term compared to his first, there are still nearly 50 empty seats. But replacing Leo’s voice with more combative, less experienced voices like Trump aide Mike Davis means that nominating candidates for those seats will likely be a slower, more fraught process than in Trump’s first administration.
“Conservative judges are going to be much more open to stepping down if they’re confident that their replacements will be high quality,” former Bush administration lawyer Ed Whelan told The New York Times. “Trump’s bizarre attack on his judicial appointments in his first term doesn’t inspire confidence.”
Even the president, as he raged at Leo, seemed to recognize the importance of the latter’s project. Referring to the trade court decision, he said, “Hopefully, the Supreme Court will reverse this horrible, Country threatening decision, QUICKLY and DECISIVELY.” But lashing out at a “den mother” is hardly the way to curry favor with those who are the beneficiaries of their care.