Billionaire Sues for $10B Over Epstein Story, Loses Again

A federal judge in Miami threw out President Donald Trump's $10 billion defamation lawsuit against The Wall Street Journal and Rupert Murdoch on Saturday, October 31, 2026, and this time he slammed the door. U.S. District Judge Darrin P. Gayles dismissed the case with prejudice, which means it can't be refiled. It was the second time this year he'd reached the same conclusion. "As with his first attempt, he has failed," Gayles wrote in a 20-page decision. "Grasping at straws, the Amended Complaint attempts to manufacture flaws with the investigation."

The man at the top of the American state sued a newspaper for a story about his ties to Jeffrey Epstein. Legal analysts who spoke with CNN said they could not recall another instance of a sitting president suing a news outlet over a story.

Who Has the Power

The suit grew out of a July 17, 2025 Journal story describing a sexually suggestive letter and drawing that bore Trump's name and appeared in a 2003 album compiled for Epstein's 50th birthday. The paper said Ghislaine Maxwell, who is serving a 20-year sentence for procuring underage girls to be sexually abused by Epstein, collected the letter. Trump filed in Miami the next day, July 18, 2025, accusing the paper and its reporters of having "knowingly and recklessly" published "numerous false, defamatory, and disparaging statements."

The defendants weren't exactly powerless either. They included News Corp's chairman emeritus and a corporate media empire. So this was one pile of money and influence squaring off against another, and the courtroom was just the arena. Even the amended complaint claimed Murdoch told the president "I will handle it" during a phone call about the article, according to Newsweek's earlier reporting.

What They're Calling "Order"

Gayles held that Trump did not plausibly allege actual malice, the standard from the Supreme Court's 1964 ruling in New York Times Co. v. Sullivan. "Indeed, 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," the judge wrote.

One of Trump's arguments deserves a second look. He claimed the Journal should have held its story after he denied writing the letter. The judge shot it down. "Were that the law, any time a public figure or his team denies an accusation, journalists would be immediately blocked from publishing negative or contradictory press," Gayles wrote. In other words, the powerful man's denial would work as a veto on the press. The judge said the argument "runs afoul of the First Amendment." He also noted the story told readers that Trump "decried the Letter as a fake and denied writing it." The judge did not decide whether Trump actually authored the letter.

Trump's legal team says it will keep going. A spokesperson told CBS News the president "will continue to hold those who mislead the American People with Fake News and smears accountable for their actions." CNN and CNBC reported that an appeal is planned. Dow Jones, the Journal's parent, said only: "We're pleased with the court's decision."

The Lawsuit as a Weapon

This isn't a one-off. Trump has a $15 billion suit against The New York Times, where a judge dismissed the original complaint, let him refile, and then told him in July to revise it again. He sued the BBC for $10 billion over its editing of his January 6, 2021 speech, and a federal judge in Miami ordered him on Oct. 22 to sit for a deposition by Dec. 11. A suit against Iowa pollster J. Ann Selzer and The Des Moines Register over a poll showing him trailing Kamala Harris was dismissed with prejudice in September. And CNN, MS NOW and Politico are now suing for restored access after he banished them from the White House in mid-September.

Legal experts have called these suits frivolous and full of holes. But they warn that winning may be beside the point. The publicity and the threat of protracted litigation can pressure news outlets and chill aggressive reporting. Whoever can afford to bleed a newsroom with legal bills gets to set the terms of what gets printed.

The Story They Wanted Buried

The Journal piece landed while Trump's administration faced scrutiny over whether it had withheld documents about Epstein's alleged sex crimes. Epstein was convicted of soliciting a minor for sex in Florida in 2008 and served 13 months in jail. He faced federal sex trafficking charges in 2019 and was found dead in his New York City jail cell before trial; his death was ruled a suicide. House lawmakers later subpoenaed and obtained a redacted version of the birthday book from Epstein's estate, which included the letter at the center of the lawsuit, and a copy was released through the House Oversight Committee.

Trump called the story "false, malicious, and defamatory." "This is not me. This is a fake thing," he said at the time. Then-White House press secretary Karoline Leavitt said: "It's very clear President Trump did not draw this picture, and he did not sign it."

The courts handed the press a win this time. They didn't do it out of love for journalists. They did it because the law, as written, tied the president's hands. Next week there'll be another motion, another appeal, another filing, and the machinery of power will keep grinding in the hope that somebody, somewhere, flinches first.