Trump's Dismissed Epstein Letter Lawsuit Is the Latest Example of His Failure To State Cognizable Claims

On July 17, 2025, The Wall Street Journal reported that a 2003 album marking the 50th birthday of financier Jeffrey Epstein, who would later be implicated in state and federal sex offenses involving underage girls, included a letter from Donald Trump, a longtime friend. The very next day, Trump sued the Journal in the U.S. District Court for the Southern District of Florida, saying "the supposed letter is a fake and the Defendants knew it when they chose to deliberately defame President Trump." The complaint sought compensatory and punitive damages "not less than $10 billion."

Last April, U.S. District Judge Darrin Gayles dismissed that lawsuit but let Trump try again with an amended complaint. On Saturday, Gayles dismissed the lawsuit again, this time with prejudice. In both cases, Gayles concluded that Trump's lawyers had fallen far short of alleging "actual malice," a crucial element of defamation cases involving public figures. That abject failure illustrates a persistent pattern in Trump's long history of frivolous lawsuits: As far as Trump is concerned, the point is to punish people for saying things he does not like, as opposed to seeking compensation for a legally cognizable injury.

What does "actual malice" mean? Trump seems to think it means that someone published a false statement "out of hatred and ill-will"—a phrase that appears in both Trump's original complaint against the Journal and in his amended complaint, which he filed on May 27, 2026. But as Gayles explains in his order, that is not what "actual malice" means.

"To plead actual malice," Gayles notes, quoting a 2018 decision by the U.S. Court of Appeals for the 11th Circuit (which includes Florida), Trump "must allege facts sufficient to give rise to a reasonable inference that the false statement was made with knowledge that it was false or with reckless disregard of whether it was false or not. This is a subjective test, focusing on whether the defendant 'actually entertained serious doubts as to the veracity of the published account, or was highly aware that the account was probably false.'"

The Supreme Court established that standard in the 1964 case New York Times v. Sullivan, saying it was required by the First Amendment. "In these cases," the 11th Circuit noted in 2016, "there is a powerful interest in ensuring that free speech is not unduly burdened by the necessity of defending against expensive yet groundless litigation."

The actual malice standard "was designed to allow publishers the 'breathing

space' needed to ensure robust reporting on public figures and events," the 11th Circuit explained. "Forcing publishers to defend inappropriate suits through expensive discovery proceedings in all cases would constrict that breathing space in exactly the manner the actual malice standard was intended to prevent. The costs and efforts required to defend a lawsuit through that stage of litigation could chill free speech nearly as effectively as the absence of the actual malice standard altogether."

That explains why Gayles, after dismissing Trump's first complaint, rejected his motion for discovery "on issues related to actual malice." Specifically, Trump was keen to find evidence that might illuminate the defendants' "state of mind," which was sorely lacking in his original complaint. "President Trump's request to conduct discovery on issues related to actual malice before filing a well-pleaded complaint contravenes the purpose behind the actual malice standard," Gayles wrote.

Denied a license for that fishing expedition, Trump's lawyers tried again to file "a well-pleaded complaint," meaning their allegations, if true, would be sufficient to infer actual malice. But according to Gayles, they did not do any better this time around. "President Trump's conclusory allegations that Defendants acted with malice because they 'knew or should have known' the statements in the Article were false are insufficient to state a claim," he writes.

The amended complaint "appears to allege that by choosing to publish the Article despite President Trump's and his team's denials, Defendants acted with actual malice," Gayles says. "In effect, President Trump argues that once he declared the Letter a 'fake,' Defendants should have disregarded everything else they learned in their investigation and not published the story. But that is not what the actual malice standard requires and runs afoul of the First Amendment. Indeed, 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."

Trump argued that the Journal's investigation was inadequate. "A failure to investigate, without more, does not establish actual malice," Gayles notes. "Rather, 'a plaintiff must show the defendant deliberately avoided investigating the veracity of the statement in order to evade learning the truth.' The Amended Complaint comes nowhere close to this standard."

In fact, the Journal's article "details a thoughtful and detailed investigation," Gayles writes. "Before running the story, Defendants contacted President Trump and his team, Justice Department officials, and the FBI for comment. President Trump and his team responded with his denial [which was quoted in the article], the Justice Department did not respond at all, and the FBI declined to comment."

Journal reporters Khadeeja Safdar and Joseph Palazzolo tried to interview Ghislane Maxwell, the Epstein associate who solicited the messages for his birthday album, but she did not respond, and "her attorney stated that she was focused on her case before the Supreme Court" involving her federal sex trafficking conviction. In a July 2025 interview with the Justice Department, according to Trump's lawyers, Maxwell said "she did not remember President Trump submitting a letter for Epstein's 50th Birthday." Judging from that statement, Gayles says, "Maxwell had little to offer to Defendants' investigation."

Safdar and Palazzolo also "reached out to other individuals named in the Birthday

Book, including Leslie Wexner and Alan Dershowitz, and to individuals involved in binding the Birthday Book," Gayles notes. "In short, President Trump's allegation that Defendants failed to conduct an adequate investigation is rebutted by the Article

and is insufficient to establish actual malice."

The amended complaint "attempts to manufacture flaws" in the Journal's investigation, Gayles says, describing those efforts as "grasping at straws." The complaint, for example, faults Safdar and Palazzolo for "reviewing the Letter before publication" rather than "obtaining a copy of the Letter." But "nothing in the law suggests that Defendants needed to obtain, retain, or publish a copy."

Speaking of grasping at straws, the complaint charges Safdar and Palazzolo with "the intentional omission of the denial from President Trump regarding whether he signed the alleged letter or whether the signature on the alleged letter is authentic." Yet the article "states, multiple times, that President Trump denies writing the Letter and that 't isn't clear how the letter with Trump's signature was prepared,'" Gayles notes. "This is more than sufficient to encompass any denial that he 'signed' the Letter or that the signature on the Letter is authentic."

In addition to Safdar, Palazzolo, and Dow Jones, which owns the Journal, Trump sued News Corporation, which owns Dow Jones; News Corporation CEO Robert Thomson; and Rupert Murdoch, the company's majority owner and emeritus chairman. But "other than stating that Dow Jones and News Corp published the Article 'at the direction of Defendants Murdoch and Thomson,'" Gayles notes, "the Amended Complaint is devoid of any allegations about how Thomson acted with actual malice."

Trump's disdain for meeting minimum legal requirements is part of a longstanding pattern. He has never been much concerned about actually winning in court, as opposed to inflicting pain on his enemies, whether he was demanding $500 million from an architecture critic who said unkind things about his plan for a Manhattan skyscraper, seeking $5 billion from a financial journalist who dared to question the extent of his wealth, suing a comedian for breach of contract based on a joke likening Trump to an orangutan, asserting that CNN defamed him by describing his reality-defying claims about the 2020 presidential election as "the Big Lie," alleging that The Des Moines Register committed consumer fraud by publishing poll results he did not like, or averring that CBS caused him $20 billion in damages by editing a 60 Minutes interview with Kamala Harris to make her seem slightly more cogent.

Although Trump plans to appeal Gayles' ruling, the Journal's editorial board said on Sunday, "the appeal isn't likely to succeed. A letter matching the Journal's description was released by Congressional investigators. Mr. Trump said he never wrote or signed the letter, but the Journal never claimed he did. It said only that the letter with the signature existed, and the Journal's stories have always included Mr. Trump's denials."

Trump "has long used lawsuits to intimidate the press, and most of the time he ends up losing," the editorial noted. "Mr. Trump, like other politicians, uses lawsuits to coerce settlements that he can tout as legal victories. He failed in this case because the Journal didn't roll over. A free press requires owners who back editors, and we couldn't do what we do without that support."