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Trump is losing a lot of court cases lately

October 15, 2026
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Trump is losing a lot of court cases lately

As Donald Trump pushes the bounds of executive power, much of his presidency is playing out in the courts. The past few weeks, the administration has been losing court cases at a fast clip, with multiple judges using Trump’s own words as reasons to rule against the administration or accusing the government of not following court orders.

“The lower courts are doing what they must. Many of these issues are not legally murky,” said Kimberly Wehle, a law professor at the University of Baltimore.

Wehle said the Supreme Court is the wild card: It has not always sided with Trump, but on other occasions the conservative majority has allowed Trump to fire independent officials, withhold billions in funds that Congress appropriated and knock down a wing of the White House and build a ballroom in its place.

Here’s what’s going on.

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Trump’s White House ban of reporters is on shaky ground

This week, a judge said Trump probably violated the First Amendment in banning CNN, MS NOW and Politico from reporting at the White House. The judge said Trump has to let them back in while the case plays out on its merits.

This is the second time the judge has ruled in favor of the news outlets, which argue they have a constitutional right to report on the president at the White House. The judge, a Trump appointee, pointed to Trump’s own complaints about unfair coverage to suggest that the ban was politically motivated, rather than for any national security reasons.

“The First Amendment extends to White House grounds as strongly if not more than pretty much anywhere,” said Seth Stern, chief of advocacy at Freedom of the Press Foundation, in an interview last month. “It’s the People’s House; it’s the center of government.”

Trump is appealing, and CNN’s Editor in Chief Mark Thompson said the case might eventually go to trial.

The administration can’t ever charge Olympian for touching the Reflecting Pool

This summer, Trump came under scrutiny for the rushed, botched renovation of the Reflecting Pool. He blamed vandals. During this stretch, David Hearn reached for a piece of liner floating in it. The former Olympian was arrested and charged by the federal government.

The Justice Department dropped the case weeks later. This month, Hearn won a ruling preventing any future prosecution of him for this.

Here, too, the judge cited Trump’s own words — his attacks of Hearn — as reason for the ruling against the Trump administration: “In the exceptional circumstances posed by this case,” D.C. Superior Court Judge Todd E. Edelman said in his court order, “the government has no right to retain the ability to compound the errors it has already made, or even to threaten to do so, at Mr. Hearn’s expense.”

Trump can’t fund campaign-style ads with taxpayer money

Controversial television ads promoting Trump have been running for weeks on national TV. They were paid for with taxpayer dollars, with $20 million Congress approved in part for memorials for officers killed in the line of duty.

The ads could run afoul of a decades-old law prohibiting taxpayer dollars for overt political campaigning, and some Republican senators criticized them. Several groups sued, and on Sunday, a federal judge blocked the ads from running — but the administration continued to run the ads for hours afterward.

Trump can’t keep knocking down trees to remake a golf course

Trump’s efforts to remake D.C. have run into plenty of pushback from lower courts, most notably at the Kennedy Center, where he was forced to take his name off the building.

This week, the administration’s nascent plans to remake a historic public golf course blew up in court. Preservationists had sued, and a judge told the administration not to start work yet by cutting down trees.

But the administration cut down hundreds of trees over the holiday weekend instead.

An enraged U.S. District Judge Ana C. Reyes berated the government for violating her instructions: “More than just being upset and furious right now, I’m just beyond disappointed in the government,” she said. “I have done everything humanly possible to give the government the benefit of the doubt in this case.”

She issued a ruling accusing the administration of rushing to cut down the trees because Trump wanted it done, effectively saying the government lied in court that it was considering environmental impacts.

The Trump administration can’t withhold counterterrorism funds from states ahead of the election

Trump’s efforts to insert the federal government into how states run elections have also repeatedly lost in court.

Last month, a federal judge said the Trump administration can’t withhold counterterrorism money from states and cities that don’t meet the government’s demands on how to run their elections. The Constitution says states run their own elections and doesn’t give the executive branch any role.

There’s not evidence the Federal Reserve criminally mishandled its renovation

Trump had used accusations of mismanagement of the Federal Reserve’s major building renovations to try to oust the former chairman, Jerome H. Powell, who resisted Trump’s pressure to lower interest rates.

The government briefly pursued a criminal case against Powell, then dropped it. A federal judge likened it to a political pressure campaign, and politicians on both sides warned that meddling with the Federal Reserve would upset markets.

“It just seems like there is waste with the renovation,” said Neama Rahmani, a former federal prosecutor, in an interview earlier this year, “but that happens all the time. That doesn’t make it criminal.”

An independent watchdog in the Federal Reserve effectively agreed, finding that the agency failed to stop the renovation’s costs from ballooning but that there isn’t evidence laws were broken. Powell remains on the Federal Reserve Board of Governors, though his term as chair has ended.

The board is one seat away from a majority of Republican appointees. And this month Trump ramped up his efforts to try to fire board member Lisa Cook. The Supreme Court temporarily prevented Trump from doing it, but there’s an ongoing lawsuit, and Trump just created a commission to investigate allegations of mortgage fraud, which Cook denies. Presidents nominate members to the influential bank, but they can only fire them with cause.

Amber Phillips writes The 5-Minute Fix newsletter, a quick analysis of the day’s biggest political news. Send her an email here, or ask a question that could be featured in an upcoming newsletter.

The post Trump is losing a lot of court cases lately appeared first on Washington Post.

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