Trump’s Rift With Federalist Society Deepens in Second Term

By Manisha Sahu | America News World
November 23, 2025

During Donald Trump’s first term in the White House, few organizations outside his formal administration wielded as much influence over judicial nominations as the Federalist Society. The 43-year-old conservative legal group, long known for its commitment to originalism and textualism, played a significant role in shaping the federal judiciary. Guided primarily by Leonard Leo, then the group’s executive vice president, the society helped establish a streamlined pipeline for conservative jurists who shared a traditional, restrained view of constitutional interpretation.

President Donald Trump appears with Judge Neil Gorsuch and Supreme Court Justice Anthony Kennedy at Gorsuch’s swearing-in ceremony held in the White House Rose Garden. Led in part by Leonard Leo, the Federalist Society cultivated a strong network of conservative jurists — a framework that may fall short of Trump’s expectations in his second term.(New York Times)

Trump embraced that pipeline enthusiastically. He effectively outsourced much of the judicial selection process to attorneys closely associated with the Federalist Society. It was a mutually beneficial partnership: Trump gained credibility among conservative legal circles and grassroots Republican voters, while the society achieved unprecedented influence in placing its preferred judges on the federal bench, including the Supreme Court.

But the alliance that once appeared unshakeable has begun to fracture during Trump’s second term. As the judiciary — including some of the very judges he appointed — issued rulings that blocked or questioned the legality of certain Trump administration policies, the former president has increasingly turned his criticism toward the Federalist Society itself. What was once celebrated as a strategic partnership has now become a public rift, raising questions about the future of conservative jurisprudence and the independence of the nation’s judiciary.

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A Fractured Partnership

The clearest sign of the fallout came in May, when Trump posted a lengthy and blistering attack on social media. In it, he called Leonard Leo a “sleazebag” who “openly brags how he controls Judges.” Trump accused the Federalist Society of giving him “bad advice” and selecting judges who, in his view, did not show proper loyalty when faced with cases assessing the legality of his executive actions.

The comments shocked many in legal and political circles. For decades, the Federalist Society had been regarded as the intellectual backbone of conservative legal thought — an organization that avoided overt political engagement while providing forums for debates on constitutionalism and the separation of powers. Its influence reached from law schools to federal courtrooms, shaping generations of right-leaning attorneys and judges.

To see Trump turn so sharply on the very group that helped deliver many of his most high-profile judicial successes is indicative of a deeper and growing divide: the difference between a legal philosophy rooted in constitutional restraint and a political movement seeking more immediate, outcome-driven loyalty.

Judges Caught in the Middle

Some of the tensions stem from rulings that did not go Trump’s way. Federal judges appointed during his first term — including some selected with the Federalist Society’s input — have issued decisions blocking certain policy moves on administrative, procedural, or constitutional grounds. These decisions, from immigration directives to regulatory rollbacks, have reinforced that conservative judges are not necessarily political allies.

Judges aligned with the Federalist Society often adhere to a strict textualist view of the law, which means they emphasize the written statute or constitutional text rather than a broader interpretation aligned with contemporary political needs. For Trump, whose governance style has often relied on sweeping executive orders and rapid policy shifts, such judicial restraint can be an obstacle.

Legal scholars note that this tension is not new. Previous Republican presidents, including George W. Bush, encountered similar frustrations when conservative judges ruled in unexpected ways. But the Trump era has amplified the disconnect, turning what was once private tension into a public spectacle.

Federalist Society’s Silence and Strategy

The Federalist Society has traditionally avoided political fights. Its leaders emphasize that the organization does not endorse judges, politicians, or legislation. Their mission, they say, is strictly educational: to encourage debate and uphold a particular vision of constitutional interpretation.

In keeping with its longstanding stance, the group has not responded directly to Trump’s criticisms. Some members have privately expressed concern that engaging in a public feud with a former president — and current leader of the Republican Party — would only deepen divisions and blur the organization’s intellectual objectives with partisan politics.

However, Trump’s attacks have caused discomfort within the group. Some fear that the rift could weaken the society’s influence over future judicial nominations. Others worry that Trump’s emphasis on personal loyalty over constitutional consistency could reshape the criteria used to select judicial nominees in the years ahead.

Leonard Leo’s Controversial Position

Leonard Leo’s role in the conflict has drawn particular attention. Once revered among conservative activists for helping shape the Supreme Court’s rightward shift, Leo has recently faced increased scrutiny — not only from Trump but also from political opponents who allege that his advocacy networks wield excessive influence.

Trump’s claims that Leo “controls judges” play into broader debates about the role of external organizations in shaping judicial behavior. Legal analysts argue that while Leo has played an influential role in identifying and supporting conservative jurists, there is no evidence that he controls judicial decisions. Instead, they suggest that Trump’s grievances reflect frustration with judges who prioritize legal doctrine over political alignment.

A Wider Reckoning for Conservative Legal Movement

The conflict between Trump and the Federalist Society signals a larger struggle within the conservative legal movement. On one side are traditional conservatives who emphasize judicial restraint, limited government, and adherence to constitutional text. On the other are political actors who prioritize loyalty and desired policy outcomes, even if achieving them requires pushing the boundaries of established legal norms.

This divide is likely to shape judicial politics for years to come. If Trump continues to distance himself from the Federalist Society, future Republican judicial nominees may increasingly come from outside the organization’s traditional circles — potentially shifting the profile of conservative judges toward more openly ideological or populist candidates.

Looking Ahead

As Trump’s second term progresses, the relationship between the presidency and the judiciary will remain central to national governance. The Federalist Society, once celebrated as a key architect of the conservative judicial renaissance, now finds itself navigating a political landscape defined by shifting loyalties and heightened expectations.

Whether the rift heals or deepens, one thing is clear: the debate over the future of the conservative legal movement — and the role of the judiciary in American democracy — is far from over.