An Obama Judge Tosses Trump's $10 Billion Wall Street Journal Suit for Good. Now the Paper Wants Him to Pay Its Lawyers

President Trump's lawsuit against The Wall Street Journal over its Jeffrey Epstein birthday-letter story is finished in federal district court. On Saturday, U.S. District Judge Darrin Gayles in Miami, an Obama appointee, threw out Trump's amended complaint with prejudice, which means he cannot file the same claims there again.

"This Order addresses President Donald J. Trump's second attempt to plead that Defendants... acted with actual malice," Gayles wrote in the 20-page order. "As with his first attempt, he has failed."

The defendants were Dow Jones, which publishes the Journal, its parent News Corp., Rupert Murdoch, News Corp. CEO Robert Thomson, and reporters Khadeeja Safdar and Joseph Palazzolo.

The story Trump says is fake

The suit was over a July 17, 2025, Journal article reporting that a bawdy letter bearing Trump's name, framed by a hand-drawn outline of a naked woman, was among the letters Ghislaine Maxwell gathered for Epstein's 50th birthday album in 2003. Trump denied it before the story ran. "This is not me. This is a fake thing. It's a fake Wall Street Journal story," he told the paper. He sued the next day.

The order says Trump also told Murdoch directly that he had not signed or sent the letter, and that when Murdoch said he would "handle it," Trump believed the story would not run. It ran two days later.

In September 2025, the House Oversight Committee released the birthday book it had subpoenaed from Epstein's estate. It included a page matching the Journal's description. The judge did not treat that page as settled fact. Because Trump disputes that it is authentic and denies writing or signing it, Gayles said he could not consider it at this stage, and that whether Trump wrote the letter is a question of fact the court did not decide.

Why the judge said Trump lost

Public figures suing for defamation have to show "actual malice": that the publisher knew a statement was false or had serious doubts about it and published anyway. That standard comes from the Supreme Court's 1964 ruling in New York Times Co. v. Sullivan, and the 11th Circuit requires a plaintiff to plead it plausibly before getting any discovery. Gayles opened the order with a long passage from Sullivan.

"The allegations regarding malice are conclusory, vague, sometimes inconsistent with the Article, and often irrelevant to whether Defendants knew or should have known that the statements in the Article were purportedly false," he wrote.

Denial is not enough. Trump argued that once he called the letter a fake, the paper should not have published. Gayles said that would let any public figure stop negative stories just by denying them, and noted the article itself told readers Trump "decried the Letter as a fake and denied writing it."

The investigation. The judge said the article "details a thoughtful and detailed investigation," pointing to requests for comment to Trump's team, the Justice Department, the FBI, Maxwell's lawyer, Leslie Wexner and Alan Dershowitz. "Grasping at straws, the Amended Complaint attempts to manufacture flaws with the investigation," he wrote. He rejected the claim that the reporters had to possess a copy of the letter rather than just review it.

Maxwell. Trump's complaint said Maxwell told Justice Department officials in July 2025, under penalty of perjury, that she did not remember Trump submitting a letter. Gayles called the focus on Maxwell "a red herring," noting that her interview came after the article ran and that, by Trump's own account, she had little to offer.

The signature. Trump also leaned on a September 2025 Journal follow-up comparing the letter with his known signatures and drawings. Gayles wrote that it was "unclear" why Trump said it showed the signatures "could not be more different," since it "contains several examples where President Trump's actual signature and sketches are similar."

The legal bills

The Journal's side asked the court to make Trump pay its attorneys' fees under Florida's or New York's anti-SLAPP law, which targets suits filed over speech on public issues. "The Court agrees that President Trump's defamation claims lack merit," Gayles wrote, but he held off on fees because it is not yet clear which state's law applies. He gave the defendants 30 days to file a fee motion and kept jurisdiction to decide it.

A Dow Jones spokesperson told CNBC, "We're pleased with the court's decision." A spokesman for Trump's legal team said the president plans to appeal: "President Trump will continue to press forward in his powerhouse lawsuit against the Wall Street Journal and all of the other defendants. The President will continue to hold those who mislead the American People with Fake News and smears accountable for their actions."

Gayles first dismissed the suit in April, finding no plausible claim of actual malice, but let Trump try again. Trump asked for discovery before amending, the court denied it, and he filed the amended complaint on May 27. The court heard arguments on Aug. 5 before Saturday's ruling. An appeal would go to the 11th Circuit in Atlanta.