Trump’s $15 Billion Showdown: From Lucky Loser to a Lawsuit Against The New York Times

President Donald Trump has launched a massive $15 billion defamation lawsuit against The New York Times, accusing the paper of spreading lies about his business record, political career, and ties to Jeffrey Epstein. The lawsuit raises sharp questions about media freedom, the First Amendment, and how far a sitting president can go in challenging the press.

Ama Boah

Sep 16, 2025 - 10:21

President Trump on the left with the New York Times building on the right

Trump filed the suit in Florida against The New York Times, four of its reporters, and Penguin Random House. He claims:

A 2024 book (Lucky Loser: How Donald Trump Squandered His Father’s Fortune and Created the Illusion of Success) damaged his reputation.
Articles falsely suggested shady finances and improper ties to Jeffrey Epstein.
The paper acted with “intentional malice” and served as a political weapon against him during the 2024 campaign.
The reporting caused financial harm, including alleged losses to Trump Media & Technology Group.

In his words, the Times has become a “mouthpiece for Democrats” that has smeared him for profit.

While the lawsuit is headline-grabbing, experts say winning $15 billion is unlikely. Here’s why:

The defamation standard is high: As a public figure, Trump must prove “actual malice” — that the Times knowingly published lies or showed reckless disregard for the truth.
Free speech protections: The First Amendment shields opinion, commentary, and political reporting. If the claims fall under protected speech, the case could collapse.
Proof of damages: Trump will need to link specific financial or reputational harm directly to the reporting. That’s often the hardest part in court.

Dismissal or reduction: The Times is expected to push for dismissal, arguing much of the reporting is opinion or fact-based.
Settlement: To avoid a lengthy courtroom battle, both sides could reach a financial or public apology deal.
Political theater: Even without a courtroom win, the lawsuit lets Trump frame himself as battling “media corruption”, a narrative that could energize his supporters ahead of 2026 midterms.

This lawsuit could have ripple effects far beyond Trump and the Times:

Media outlets may become more cautious, adding disclaimers or legal reviews before publishing stories on high-profile figures.
Press freedom debates will intensify, reviving arguments over whether U.S. defamation law should be tougher on journalists.

For Trump, it keeps the spotlight squarely on him, reinforcing his combative stance against what he calls “fake news media.”

Source:

CNN/BBC