A federal judge in Florida has officially reminded Donald Trump’s legal team that lawsuits are supposed to resemble legal documents—not campaign flyers or bedtime stories written to soothe the boss’s fragile ego.
On September 19, 2025, U.S. District Judge Steven Merryday dismissed Trump’s $15 billion defamation lawsuit against The New York Times, calling the 85-page complaint “improper and impermissible.” Translation: it was more bluster than brief.
Eighty-Five Pages of Ego Polishing
The complaint, filed September 15, was reportedly so bloated that the first actual legal count didn’t appear until page 80. Instead, readers were treated to long passages alleging that The Times had maliciously tried to destroy Trump’s business empire, sabotage his campaign, and generally refuse to recognize him as the greatest businessman since Croesus.
Among the supposed offenses: three New York Times articles, a book published by Penguin Random House (Lucky Loser—ouch), and reporting on TV producer Mark Burnett’s role in manufacturing Trump’s celebrity status. Yes, apparently defamation now includes telling people that “The Apprentice” wasn’t a documentary.
Judge Merryday’s Reality Check
In language that deserves to be carved into marble, Judge Merryday wrote that a complaint is not a megaphone for political rants, a public relations stunt, or “the functional equivalent of Hyde Park Speakers’ Corner.” In other words: “Mr. Trump, this is a courtroom, not a rally stage.”
And just in case Trump’s lawyers were too busy drafting their next loyalty oath to notice, the judge reminded them of Rule 8: keep it short and plain.
28 Days to Try Again
The court struck the complaint but gave Trump’s team 28 days to refile in a professional manner. Which raises the obvious question: Can his attorneys physically produce a filing under 80 pages without slipping in an ode to Trump’s golf swing?
Don’t bet on it.
If past performance is any guide, the amended complaint may read like:
“Paragraph 1: Your Honor, Mr. Trump is very handsome, successful, and the best president ever.”
“Paragraph 2: The New York Times was mean and hurt his feelings.”
“Paragraph 3: Damages requested: $15 billion plus a parade.”
The Times Responds
The New York Times seemed positively tickled by the dismissal, noting that the judge recognized the lawsuit for what it was: a political screed disguised as a legal filing. Penguin Random House also applauded, probably relieved that the courts still distinguish between libel and book reviews with bad Amazon ratings.
Coming Soon: Lawsuit 2.0
Trump’s spokesperson confirmed they plan to refile. No word yet on whether the new complaint will stick to facts, but don’t be surprised if it comes bound in gold leaf, signed in Sharpie, and prefaced with the words: “Once upon a time, the Fake News tried to stop a very stable genius…”
Bottom Line
At this point, one has to wonder if Trump’s legal team isn’t actually a law firm at all, but a carefully curated squad of ego-supplicants masquerading as attorneys—professionals whose main expertise seems to be crafting 85-page love letters to their client rather than following the rules of a federal courtroom. Who needs motions and briefs when you can have endless flattery, lavish praise, and reminders that “no one has ever been more tremendously successful, Your Honor, than our client”?
We are so amused.
— Steve
The Original 85-page Complaint (Case 8:25-cv-02487 Document 1 Filed 09/15/25)
U.S. District Judge Steven Merryday’s Ruling (Case 8:25-cv-02487-SDM-NHA Document 5 Filed 09/19/25 )
Even under the most generous and lenient application of Rule 8, the complaint is decidedly improper and impermissible. The pleader initially alleges an electoral victory by President Trump “in historic fashion” — by “trouncing” the opponent — and alludes to “persistent election interference from the legacy media, led most notoriously by the New York Times.” The pleader alludes to “the halcyon days” of the newspaper but complains that the newspaper has become a “full throated mouthpiece of the Democrat party,” which allegedly resulted in the “deranged endorsement” of President Trump’s principal opponent in the most recent presidential election. The reader of the complaint must labor through allegations, such as “a new journalistic low for the hopelessly compromised and tarnished ‘Gray Lady.’”
The reader must endure an allegation of “the desperate need to defame with a partisan spear rather than report with an authentic looking glass” and an allegation that “the false narrative about ‘The Apprentice’ was just the tip of Defendants’ melting iceberg of falsehoods.” Similarly, in one of many, often repetitive, and laudatory (toward President Trump) but superfluous allegations, the pleader states, “‘The Apprentice’ represented the cultural magnitude of President Trump’s singular brilliance, which captured the [Z]eitgeist of our time.” The complaint continues with allegations in defense of President Trump’s father and the acquisition of the Trumps’ wealth; with a protracted list of the many properties owned, developed, or managed by The Trump Organization and a list of President Trump’s many books; with a long account of the history of “The Apprentice”; with an extensive list of President Trump’s “media appearances”; with a de tailed account of other legal actions both by and against President Trump, including an account of the “Russia Collusion Hoax” and incidents of alleged “lawfare” against President Trump; and with much more, persistently alleged in abundant, florid, and enervating detail.
