Trump suffers rare court setbacks amid broader record of legal success

President Donald Trump has enjoyed considerable success in the courts during his second term. Federal judges and the Supreme Court have allowed key parts of his immigration agenda to proceed, upheld major personnel actions across the executive branch and endorsed an expansive view of presidential authority in several high-profile disputes.

But over the past two weeks, the administration suffered two notable legal setbacks: one involving the John F. Kennedy Center for the Performing Arts and another concerning a controversial compensation fund created through a settlement with the Internal Revenue Service.

Kennedy Center Ruling Reverses Renaming Effort

The first loss came on May 29, when U.S. District Judge Christopher Cooper ordered that Trump’s name be stripped from the John F. Kennedy Center for the Performing Arts. D.C. Cooper, an Obama appointee, also temporarily blocked the administration’s plan to shut the landmark Washington, D.C. venue for two years of renovations, which had been scheduled to begin on July 6.

The backstory starts in December 2025, when a board stacked with Trump’s handpicked allies voted to rebrand the arts complex as the “Trump-Kennedy Center,” and signage bearing the new name went up on the building. Ticket sales declined sharply in the months that followed, and artists began canceling performances in protest. In February 2026, Trump announced the center would be closed for a sweeping overhaul.

Rep. Joyce Beatty, an Ohio Democrat who had been a member of the center’s board before her voting rights were stripped, filed suit to stop both moves. 

Judge Cooper’s ruling was sweeping and pointed. In a 94-page opinion issued on what happened to be President Kennedy’s birthday, he wrote that “the Kennedy Center's organic statute makes crystal clear that the Center is to be named for President Kennedy, and it cannot bear any other formal name or public memorial based on the Board’s unilateral say-so. Congress gave the Kennedy Center its name, and only Congress can change it.”

On the closure question, Cooper found that the board had not properly weighed its legal obligations to the institution before voting to shutter it, though he left open the possibility that a future board vote could still authorize renovations.

Trump reacted with characteristic directness. In a post on Truth Social, he blasted Cooper and suggested Congress should take the whole institution back: “We are going to be working with Congress to transfer this failing Institution back to them so they can make a determination as to what to do with it.”

A Justice Department spokesperson said in the statement that the agency “will continue to defend President Trump’s ability to restore the Center to its former glory as the finest performing arts center in the country – if not the world.”

For now, Trump’s name is coming off the building.

Court Halts Anti-Weaponization Fund

The second setback involved a program that drew criticism from an unusual source: members of Trump’s own party.

In mid-May, the Justice Department announced the creation of the “Anti-Weaponization Fund,” a nearly $1.8 billion pool of taxpayer money intended to compensate individuals who claimed they had been unfairly targeted or persecuted by previous administrations. 

The fund was established not by Congress, but through a settlement agreement in a lawsuit Trump himself had filed against the IRS over the leak of his tax returns. Under the settlement’s terms, Trump and his family received a formal apology but no cash. The money in the new fund, however, would be available to a broad universe of other claimants.

Critics immediately pointed out that this project was an extraordinary arrangement: a fund of public money, created without congressional authorization, through a lawsuit in which the president was simultaneously the plaintiff and the head of the executive branch overseeing the defendant agency. 

A group of 35 former federal judges—appointed by Democratic and Republican presidents—filed a motion arguing that the entire legal vehicle was, in their words, “a fraud on the court.”

On May 29, the same day as the Kennedy Center ruling, U.S. District Judge Leonie Brinkema, in the Eastern District of Virginia, issued a temporary order halting all operations of the fund while she considered its legality. 

Challengers had argued that money could flow out the door and become impossible to recover before the court could act, and the judge agreed that the risk was serious enough to require a pause.

The political fallout was fast. Democrats called the fund a giveaway to Trump allies. Crucially, even some Republicans in Congress balked, and reports emerged that the fund was throwing the president’s legislative agenda into turmoil. 

By June 1, acting Attorney General Todd Blanche made it official: the Anti-Weaponization Fund was dead. DOJ’s said in a statement on X that it “disagrees strongly” with Brinkema’s ruling but would comply.

Trump later told ABC News he accepted the outcome, saying: “We are subject to the courts. At this moment, that’s what it is.”

A Broader Pattern of Judicial Success

Despite the recent setbacks, Trump’s overall record in the courts remains favorable.

During the Supreme Court’s recent terms, the administration secured a series of significant victories on emergency applications and merits cases. The court permitted the administration to proceed with major personnel actions, enforce restrictions on transgender military service, revoke Temporary Protected Status for hundreds of thousands of Venezuelans and resume certain deportation policies.

In Trump v. CASA, one of the most consequential institutional rulings of the last term, the court limited the ability of lower-court judges to issue nationwide injunctions, reducing a tool frequently used to block federal policies.

But the administration has not prevailed in every major dispute. Most notably, the Supreme Court struck down Trump’s tariff program in a 6–3 decision, concluding that the International Emergency Economic Powers Act does not authorize the president to impose tariffs.

The administration has also faced setbacks in immigration litigation, including challenges involving its use of the Alien Enemies Act.

What’s Still Coming

The Supreme Court’s term is not yet complete. Roughly three dozen cases remain pending, with decisions expected by late June or early July.

Among the most closely watched are West Virginia v. B.P.J. and Little v. Hecox, which concern state laws restricting participation by transgender athletes in girls’ and women’s sports. 

The court’s conservative majority has signaled sympathy for the laws, and a ruling in the states’ favor would validate policies Trump has championed aggressively. The cases carry implications for athletics and for how the 14th Amendment and Title IX apply to gender identity more broadly.

Another major case, Trump v. Slaughter, addresses the president’s authority to remove officials from independent regulatory agencies. The outcome could reshape the balance of power between the White House and agencies traditionally insulated from direct presidential control.

Trump’s legal record is already more favorable than his critics often acknowledge, and the decisions ahead could add substantially to the ledger. But as the past two weeks illustrate, having the courts on your side most of the time does not mean having them on your side all of the time.