On September 18, 2025, former President Donald Trump escalated his campaign against America’s media giants with a bombshell lawsuit against The New York Times, seeking an eye-popping $15 billion in damages. The 85-page complaint, according to NBC News, alleges that the Times defamed Trump through its reporting on his finances, inheritance, and business legacy, as well as through material in the book "Lucky Loser: How Donald Trump Squandered His Father’s Fortune and Created the Illusion of Success," penned by Times reporters Susanne Craig and Russ Buettner. Trump claims these stories were not just inaccurate, but published with the intent to damage his "hard-earned and world-renowned reputation for business success" and to "sabotage his 2024 candidacy for President of the United States."
Yet, legal experts and First Amendment scholars across the spectrum have been quick to dismiss the lawsuit as lacking the necessary teeth. As Katie Fallow of Columbia University’s Knight First Amendment Institute told NBC News, "The complaint is full of bluster, but short on any allegations of specific false statements of fact that would meet the rigorous standards for defamation claims brought by public figures." The core of the legal challenge rests on the claim of "actual malice"—that the Times acted with knowledge of falsity or reckless disregard for the truth. But Trump’s complaint, as Fallow and others point out, seems to equate strong editorial dislike or political opposition with the legal threshold for malice, a standard set by the 1964 Supreme Court decision in New York Times Co. v. Sullivan.
This is not Trump’s first foray into the courtroom against media outlets. In the past year alone, he has sued ABC and anchor George Stephanopoulos for $16 million over statements regarding the civil suit brought by E. Jean Carroll—an action which ended in a settlement. He also sued CBS for allegedly editing a Kamala Harris interview to make her appear more coherent, with that network settling for another $16 million. According to The New York Times, Trump’s history with defamation lawsuits stretches back decades, including a $500 million suit in the 1980s against Chicago Tribune critic Paul Gapp, which was ultimately dismissed as protected opinion.
But the stakes are higher when the plaintiff is not just a celebrity or business magnate, but a former president and likely political candidate. As NBC News explains, the Times’ historic reputation as the "newspaper of record" means that its response to Trump’s lawsuit could set a precedent for the entire industry. Legal scholars warn that a capitulation by the Times would embolden further attacks on press freedom, especially against smaller outlets with fewer resources to fight back.
Trump’s legal actions have not been limited to print media. Last October, he targeted pollster J. Ann Selzer and The Des Moines Register, accusing them of "election interference" due to inaccurate polling, and he has previously sued The Wall Street Journal’s parent company for reporting on his birthday message to Jeffrey Epstein. Each of these lawsuits, according to First Amendment advocates, is less about winning in court than about intimidating critics and chilling investigative reporting.
Indeed, the impact of Trump’s legal crusade has rippled through the media landscape. According to reporting by The New York Times, the recent settlements with ABC and CBS were not just legal losses for the networks, but strategic moves by their parent companies to avoid regulatory headaches. Paramount, which owns CBS, delayed its planned $8 billion sale to Skydance until the defamation suit was resolved, wary of approval from a Trump-influenced Federal Communications Commission. The fallout was swift: CBS News’ president and the executive producer of "60 Minutes" resigned, and the network ended Stephen Colbert’s contract—despite Colbert’s show being the top-rated late-night comedy program and a frequent source of Trump criticism.
Meanwhile, ABC pulled Jimmy Kimmel’s show after a monologue in which Kimmel accused Trump’s "MAGA gang" of exploiting the assassination of Charlie Kirk for political gain. The network’s decision came on the heels of a public threat from FCC chairman Brendan Carr, who ominously warned Disney (ABC’s parent company), "We can do this the easy way or the hard way." Such interventions, say media watchdogs, signal a new era where the threat of government action looms over editorial decisions.
It’s not just external pressure, either. Jeff Bezos, owner of The Washington Post, has reportedly imposed new editorial restrictions to avoid provoking Trump’s ire, barring the paper’s editorial board from endorsing Kamala Harris in 2024 and tightening standards for opinion pieces. The result, according to The New York Times, has been a wave of resignations among the Post’s opinion writers and editors—another sign of the chilling effect Trump’s tactics are having on the free press.
First Amendment scholars and press advocates argue that these lawsuits and settlements represent a dangerous trend. As Robert Reich wrote in The Guardian, "Trump’s efforts to silence media criticism of him and his administration constitute another of his attacks on democracy." Reich and others have called for legislative reforms, including stricter defamation standards for presidents—such as requiring proof that a false statement materially impaired a president’s ability to do the job, or even barring presidents from filing such lawsuits altogether. Additionally, they suggest that antitrust authorities should prevent ultra-wealthy individuals or corporations with diverse business interests from buying major news outlets, to ensure the public’s right to know isn’t subordinated to private financial interests.
The chilling effect isn’t hypothetical. CBS’s owners reportedly agreed to hire an ombudsman—Kenneth R. Weinstein, formerly of the conservative Hudson Institute—to police the network for bias, a move seen as a direct concession to Trump’s demands. The richest people in America now control many of the nation’s most influential media platforms: X (formerly Twitter), CBS, and The Washington Post among them. Critics argue that these business titans are more invested in their broader empires than in protecting journalistic independence.
For now, the fate of Trump’s lawsuit against The New York Times remains uncertain. Legal experts agree that, given the high bar set by New York Times Co. v. Sullivan, the former president is unlikely to prevail in court. But the larger battle—for the soul of American journalism and the health of democracy itself—is far from over. As one First Amendment advocate put it, "The Times, the Harvard of newspapers, should understand its role here accordingly." Anything less, they warn, risks a future in which powerful figures use the law not to seek justice, but to muzzle dissent and rewrite the public record.
In an era where the lines between political power, business interests, and media influence have never been more blurred, the outcome of this clash may well shape the future of press freedom for years to come.
