Trump v. The New York Times: When Losing Is the Strategy
How Donald Trump turns defamation lawsuits into political weapons
On September 16, Donald Trump filed a $15 billion lawsuit against The New York Times and Penguin Random House in Florida. The suit alleges that the Times and a book titled Lucky Loser: How Donald Trump Squandered His Father’s Fortune and Created the Illusion of Success defamed him in a coordinated campaign to damage his reputation and political standing.
This is not Trump’s first legal action against a media outlet, and it won’t be his last. In fact, this is part of a pattern, one that has become central to how he exerts power in the public sphere.
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The Pattern: Defamation as Political Playbook
Just this year, Trump has filed or threatened defamation lawsuits against the Wall Street Journal, ABC News, CBS/60 Minutes, and the Des Moines Register, among others. These are not small-dollar tantrums. The suit against the Wall Street Journal seeks $10 billion over a report that tied him to a birthday greeting allegedly sent to Jeffrey Epstein. The CBS and ABC cases resulted in settlements reportedly totaling over $30 million combined.
What’s notable is not just the volume of lawsuits, but how Trump uses them. These legal actions don’t follow the logic of someone trying to clear their name or correct a falsehood. They follow the logic of someone who sees litigation as a political instrument.
The Legal Weakness Is the Point
Trump’s lawsuits tend to arrive fast, loud, and legally fragile. His case against the Wall Street Journal may already be in trouble because he allegedly failed to comply with Florida law, which requires five days’ written notice to a news outlet before filing a defamation suit. It’s a basic procedural step, one that any competent legal team knows to follow. That it might have been skipped suggests that winning the case wasn’t the goal. Making headlines was.
In the case against the New York Times, Trump is arguing not just that one article harmed him, but that there is a broader pattern of defamation across years of reporting and commentary. That framing might also be strategic. By alleging a long-standing campaign of damage rather than a single offending article, he may be trying to avoid the same timing issue that threatens the Wall Street Journal case. Whether that will work remains to be seen.
Losing Is the Strategy
Trump doesn’t need to win these lawsuits for them to serve their purpose. In fact, losing may be part of the strategy. These cases dominate the news cycle, cast doubt on his critics, and give him a new grievance to feed his base. Each one becomes a campaign prop, a fundraising hook, or a distraction from deeper legal trouble.
Like playing the stock market or gambling, one success can make up for several losses. One multi-million-dollar settlement offsets filing costs in multiple cases, but at the same time, the narrative-control is priceless. However, most valuable is the press attention and the chilling effect on speech.
This is not litigation in the traditional sense. It’s lawfare, the use of legal mechanisms not to resolve disputes, but to exhaust, intimidate, and control. Trump’s targets, often media outlets or individual journalists, are forced to spend time, money, and energy defending themselves. Even if the claims are baseless, the cost of defense is real. And for smaller organizations, that cost can be existential.
From Real Estate to Politics: A Familiar Tactic, New Stakes
It’s a cynical use of the court system, but also a familiar one for Trump. He’s been using lawsuits this way since his real estate days, threatening or filing legal actions to extract concessions, delay accountability, or simply bully opponents. What’s different now is the scale and the stakes. When a president uses defamation lawsuits as a political weapon, the effect goes beyond the newsroom. It chills speech, corrodes democratic norms, and undermines trust in the judicial system.
There is nothing illegal about filing a lawsuit. But when litigation becomes a political tool rather than a legal one, it deserves scrutiny—not just from the courts, but from all of us.
What You Can Do
Support independent journalism. Legal intimidation works best when institutions are underfunded and under-defended.
Push for strong anti-SLAPP laws in your state. These laws can help prevent abuse of the courts for political gain.
Pay attention not just to what Trump sues over—but why, when, and what he gains from the attention.
Stay Informed. Stay Loud.
Subscribe to The Coffman Chronicle for no-BS political analysis, action guides, and daily truth bombs you won’t get from corporate media.
Sources:
Trump sues The New York Times for defamation and libel, seeks $15 billion — Reuters, September 16, 2025
Trump’s Wall Street Journal suit over Epstein story faces timing hurdle — Reuters, July 22, 2025
Alarming but not unexpected: NYT lawsuit just latest example of Trump’s presidential lawfare — The Guardian, September 16, 2025
Trump sues ‘degenerate’ New York Times for $15B — Politico, September 16, 2025
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All the evil trump has done, will come back upon him .
Yes, that's crazy. But why are these companies agreeing to a settlement? That looks like a defeat.
Why aren't they fighting to defeat the despicable Trump? Especially when they are law firms.