Trump Turns on Leonard Leo Amid Judicial Disputes

On Thursday evening, former President Donald Trump sharply criticized one of his longtime allies.

This outburst followed a ruling by a three-judge panel of the U.S. Court of International Trade, which included a judge appointed by Trump during his first term. The court rejected Trump’s expansive use of the International Emergency Economic Powers Act of 1977 to authorize tariffs.

Although the ruling was quickly stayed by an appellate court pending further review, Trump launched a lengthy denunciation on his platform, Truth Social, targeting the judiciary.

While Trump has frequently attacked judges who rule against him since before his presidency, this time his ire was directed specifically at Leonard Leo and the Federalist Society. The Federalist Society is the most prominent conservative legal organization in the United States, and Leo has long been one of its influential leaders.

Trump expressed deep disappointment with the Federalist Society for providing what he called “bad advice” on judicial appointments. His harshest words were reserved for Leo, whom he labeled a “sleazebag” and a “bad person” who, in Trump’s view, might harbor antipathy toward America.

Leo played a key role in helping Trump select conservative legal figures for judicial posts and administration roles. Trump’s decision in 2016 to release a Supreme Court shortlist heavily featuring Federalist Society members helped secure support from skeptical conservatives.

However, the Federalist Society has maintained its independence and has not simply aligned with Trump. As a decentralized organization, its chapters vary widely in their political leanings. Some groups lean toward Trump-friendly views, while others remain staunchly opposed.

For every prominent Federalist Society member like John Eastman, who faced legal consequences for efforts related to the 2020 election, there are numerous judges and lawyers affiliated with the Society who have ruled against or resisted Trump.

Throughout his first term, Trump’s record at the Supreme Court—the majority of which was appointed by Republicans—was poorer than that of any modern president. Federalist Society judges repeatedly ruled against him, including in challenges to the 2020 election results.

Under President Joe Biden’s administration, the Supreme Court has continued to reject many legal arguments aligned with Trump’s MAGA movement. Recent federal court rulings have also been largely unfavorable to Trump, with Republican-appointed district judges ruling against him approximately 72 percent of the time as of May, a rate not far from that of Democratic-appointed judges.

The Supreme Court has demonstrated little leniency in Trump’s second term efforts, unanimously affirming due process rights for deportees under the Alien Enemies Act and ruling against the administration’s attempts to limit procedural protections.

While Trump has secured notable victories, such as decisions that have expanded presidential immunity and allowed him to remain on the 2024 ballot, a clear distinction remains between judicial conservatives and congressional Republicans. Most judges adhere to their principles, even when in conflict with Trump’s demands, whereas many members of Congress have not.

Importantly, the Constitution establishes Congress as a coequal and superior branch designed to check presidential power. As articulated in Federalist No. 51, ambition must be balanced by ambition.

Trump expressed bewilderment in his Truth Social post, questioning the origins of the judges who ruled against him and suggesting their decisions stem from personal animosity rather than legal reasoning.

There is a shared curiosity about why the judiciary remains steadfast when many other American institutions, especially conservative ones, appear compromised. Why have so many conservative judges remained loyal to legal principles while many Republicans have adapted their stances to support Trump’s more controversial actions?

Drawing on experience within the conservative legal community and relationships with Trump-appointed judges, part of the answer lies in differing motivations between judges and politicians.

Judges prioritize the judgment of history and the respect of their peers over popular acclaim, while politicians often seek electoral approval and immediate success.

Although both judges and lawmakers may cite public service as their motivation, politicians are more inclined to measure success by winning elections. This pragmatism can lead to compromises that judges typically resist.

In a legal system grounded in precedent rather than popular vote, judicial decisions define a judge’s legacy. For example, Chief Justice Roger B. Taney is forever remembered for the Dred Scott decision, which severely damaged his historical reputation.

Seeking popular approval can be perilous for judges, as many constitutional provisions are deliberately designed to protect minority rights and uphold the rule of law against majority pressures.

Due process protections and rights of unpopular groups have often been upheld by the courts despite lacking popular support, exemplifying the judiciary’s role as a guardian of constitutional principles.

While judicial independence can sometimes foster arrogance or detachment, it also reinforces professionalism and pride, which help preserve the constitutional order.

Attempts to intimidate judges often backfire, strengthening their resolve rather than weakening it. Some judges view such pressure as a personal affront, responding with increased determination.

This blend of commitment to the rule of law and principled defiance represents a rare instance in today’s polarized political climate where a branch of government is effectively fulfilling its constitutional role.