President Donald Trump launched yet another complaint against yet another news media outlet, this time seeking $15 billion in damages for The New York Times’ allegedly defamatory conduct.
The defamation complaint filed September 15, 2025 alleges that The New York Times Company; reporters Susanne Craig, Russ Buettner, Peter Baker, and Michael S. Schmidt; along with Penguin Random House LLC; defamed him through the 2024 book “Lucky Loser: How Donald Trump Squandered His Father’s Fortune and Created the Illusion of Success” and three articles published in the weeks before the 2024 presidential election. President Trump claims these defendants maliciously and falsely portrayed him as a failed businessman whose fame was manufactured by “The Apprentice” television producer Mark Burnett, while disregarding evidence of his longstanding business and celebrity success. The complaint argues that the book and articles were part of a coordinated campaign of “industrial-scale defamation” aimed at damaging his reputation, undermining his presidential candidacy, and influencing legal cases against him.
This is far from his first defamation rodeo with The New York Times. Donald Trump filed defamation lawsuits against The Times twice in his first term as president. Both times, the lawsuits were dismissed. In the first case, in 2020, the Trump campaign sued the newspaper claiming an October 2019 op-ed, “The Real Trump-Russia Quid Pro Quo,” was published with “extreme bias.” The court ruled the op-ed was protected speech and the campaign had no right to sue for defamation. In 2021, the president sued the newspaper alleging three reporters conspired with his niece, Mary L. Trump, to obtain confidential tax records for a 2018 series of stories. However, in 2023, a New York judge dismissed the lawsuit, citing a long-standing principle that reporters have the right to gather information without fear of liability, which is at the heart of protected First Amendment activity. The judge ordered President Trump to pay the Times’ legal fees for the trouble.
Is the Third Time the Charm?
There’s a reason why First Amendment experts deem President Trump’s lawsuits against media companies meritless. Journalists, and the efforts that go into their reporting, are rightfully protected under the First Amendment. Defamation suits, especially made by a public figure (and President Trump is among the most famous figures in the world), must surpass a high bar to succeed.
The New York Times may be regarded as a left-leaning publication, particularly in its editorials. But newspapers and journalists have no obligation to be “neutral” in their reporting. To the contrary, the ideological perspective of a journalist is precisely what the First Amendment protects. After all, the First Amendment forbids the government from “abridging the freedom of speech, or of the press”.
When it comes to defamation suits by public figures, plaintiffs must prove actual malice – that the defendants’ statements were not only false, but were published with reckless disregard for the truth. More specifically, President Trump and his legal team must prove that any of the statements pulled from Lucky Loser and the NYT articles at issue are not only false, but also that the authors knew the claims were false. It is not sufficient to simply object to the content of a report or a book or catch someone in a mistake.
The actual malice standard originated from the 1964 case New York Times v. Sullivan, which established that powerful public officials and figures cannot win defamation suits merely because the reporting is harsh, critical, or contains errors. They must prove deliberate or reckless falsehood, resulting in damage to reputation. (Donald Trump decisively won the presidential election shortly after the publication of the articles and “Lucky Loser” book, making a claim to reputation damage somewhat confounding.)
The Sullivan doctrine has troubled conservatives who believe it makes it possible for “liberal media” to stretch the truth. Well aware of Sullivan, the President has nevertheless repeatedly tried to punish media for unfavorable reporting, including via a $475 million suit against CNN in 2022, a $20 billion lawsuit against CBS for its 60 Minutes interview with Vice President Kamala Harris, and a $10 billion defamation suit against The Wall Street Journal for their coverage of a birthday card to Jeffrey Epstein which appears to bear Donald Trump’s signature. These lawsuits constitute a deliberate strategy to financially pressure news organizations while generating political messaging about media bias. As President Trump announced his latest lawsuit against the Times, he characterized it as holding accountable what he called “one of the worst and most degenerate newspapers in the History of our Country, becoming a virtual ‘mouthpiece’ for the Radical Left Democrat Party.”
By September 19, the Florida district judge Steven Merryday dismissed the latest Trump v. New York Times lawsuit, writing “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.” Merryday gave President Trump’s lawyers 28 days to amend the suit, along with a 40-page limit and a reminder of what complaints require for consideration.
This latest defamation suit will not be the one that overturns the Sullivan doctrine, but President Trump is unlikely to give up. Without Sullivan’s protections, journalists would be far more vulnerable to the pressures from billionaires and powerful government elites. If anything, journalists deserve more protections – especially from meritless lawsuits intended to silence or influence behavior (like the president’s lawsuit against CBS’s 60 Minutes) through a federal Anti-SLAPP standard. Last Congress, Senator Ron Wyden (D-Ore.) and Representatives Jamie Raskin (D-Md.) and Kevin Kiley (R-Calif.) introduced the Free Speech Protection Act. The goal of this act is to safeguard journalists and the public by offering a way to dismiss baseless lawsuits, such as defamation cases, in federal court. President Trump’s ongoing attacks on the free press highlight the urgent need for the Free Speech Protection Act, which allows journalists to quickly dismiss frivolous claims (that billionaires have limitless resources to pursue), preventing costly legal battles intended to silence their reporting.