On September 19, 2025, U.S. District Court Judge Steven Merryday delivered a stinging rebuke to President Donald Trump’s $15 billion defamation lawsuit against The New York Times, dismissing the case and leaving little doubt as to his view of its merits. The suit, which targeted articles and books published before the 2024 election, was widely derided by legal experts and the media alike as a prime example of Trump’s penchant for using the legal system as a weapon against his critics.
Judge Merryday, a federal judge appointed by President George H.W. Bush, minced no words in his ruling. He described the original 85-page complaint as “decidedly improper and impermissible,” noting it went far beyond the requirements of Rule 8 of the federal rules of civil procedure, which mandates that legal complaints be “simple, concise and direct.” Instead, the filing was replete with inflammatory language, lengthy arguments, and what the judge called a “tedious and burdensome aggregation of prospective evidence.” As quoted by CBS News, Merryday wrote, “Even under the most generous and lenient applications of Rule 8, the complaint is decidedly improper and impermissible.”
The judge’s frustration was palpable. According to NBC News, Merryday remarked, “As every lawyer knows (or is presumed to know), a complaint is not a public forum for vituperation and invective — not a protected platform to rage against an adversary.” Legal scholars echoed this sentiment, with Harvard law professor Rebecca Tushnet telling Straight Arrow News, “It is the kind of response that is appropriate to lawyers who aren’t otherwise showing that they’re capable of following the rules.”
At its core, the lawsuit accused The New York Times and Penguin Random House of publishing false statements and books, including one titled “Lucky Loser,” that allegedly damaged Trump’s reputation and business interests. The complaint cited articles that suggested Trump wanted to “rule like a dictator” and accused the authors of “falsified, distorted, and manipulated facts.” Yet, as legal experts pointed out, the suit failed to meet the high bar set by the Supreme Court’s Sullivan decision, which requires public officials to prove that defamatory statements were made with actual malice. “You actually need to show falsity. You need to show malice. Those things are not easy,” Tushnet explained.
Despite the court’s withering assessment, Judge Merryday did not close the door entirely. He gave Trump’s legal team one month to refile the complaint—this time with a strict 40-page limit and a clear mandate to adhere to procedural rules. According to Straight Arrow News, Yale law professor Robert Post observed, “He asked them to file a more professionally clean and competent complaint.” The judge made it clear, however, that his ruling was based on procedural grounds and did not address the truth or falsity of the allegations themselves.
President Trump, for his part, responded with characteristic bravado. Addressing reporters after the ruling, he declared himself “winning” the case and lambasted what he described as biased coverage by major news networks. He singled out ABC News reporter Jonathan Karl as “a terrible reporter” and accused the media of being “very unfair.” According to reports, Trump insisted, “I’m winning the cases,” and vowed to continue pursuing legal action against The New York Times in accordance with the judge’s instructions.
The New York Times welcomed the dismissal, characterizing the complaint as “a political document rather than a serious legal filing.” The paper’s stance is consistent with its responses to Trump’s previous lawsuits in 2021 and 2023, both of which were also dismissed without the courts ruling on the merits of his claims. Legal observers noted that the massive $15 billion demand and the nature of the complaint attracted attention not just for their scale, but for their apparent intent to intimidate and send a message to the media.
Indeed, Trump’s history of litigation is long and notorious. Back in 2016, USA Today identified 4,095 lawsuits filed by Trump and his businesses. Former prosecutor James D. Zirin, in his 2020 book, described Trump’s legal strategy as a direct inheritance from his mentor, Roy Cohn. “Trump saw litigation as being only about winning,” Zirin wrote. “He sued at the drop of a hat. He sued for sport; he sued to achieve control; and he sued to make a point. He sued as a means of destroying or silencing those who crossed him. He became a plaintiff in chief.”
This latest lawsuit, like many before it, fits neatly into a broader pattern of Trump’s contentious relationship with the media. Since his first term, he has popularized the term “fake news” and frequently targeted outlets that publish unflattering coverage. The recent controversies involving the Federal Communications Commission, the suspension of comedian Jimmy Kimmel by ABC, and Trump’s musings about pulling network licenses all point to a strategy that combines legal threats with public pressure campaigns. As Tushnet noted, “You don’t need to talk to a professor of the First Amendment to understand the ways in which this is stomping on our traditions of free speech and of that the government doesn’t get to control private opinion.”
For Trump, lawsuits often serve multiple purposes beyond the courtroom. As Post explained, “It’s meant to convey a number of messages. One is to his base. He says, ‘I’m really innocent here and see how innocent I am. I’m going to take the trouble to file a lawsuit.’ So the filing of the suit is meant to be a form of vindication. And second, it’s meant to indicate to The New York Times, if you continue with this form of behavior, you’re going to face a lot of costs. Not necessarily that you’re guilty, but you’re going to spend a lot of time and money defending yourself.”
Yet, as history and precedent show, defamation suits by public officials against the press are notoriously difficult to win. No president has succeeded in such a case since Teddy Roosevelt in 1913. The Sullivan standard remains a formidable barrier, ensuring that robust debate and investigative reporting remain protected under the First Amendment.
As the legal drama continues, Trump’s team has signaled their intent to refile the case, while The New York Times prepares for another round. Whether the next attempt fares any better remains to be seen, but one thing is clear: the battle lines between the president and the press are as sharply drawn as ever.
Judge Merryday’s ruling serves as a forceful reminder that, even for a sitting president, the rules of the courtroom demand clarity, conciseness, and respect for the law—a lesson that, for now, Trump’s legal team has been ordered to learn the hard way.
