The first thing experienced defense attorneys do when they get a new complaint is read it end-to-end to see if it tells a compelling story. Did my client say something so stupid, so damaging his transcript is already at FedEx Kinkos, blown up billboard size for opening statements? Is there a hidden narrative lurking that plaintiffs’ own counsel has, miraculously, somehow missed?
But once in a while, you get a complaint so full of bombast, ignorance, and braggadocio you assume the lawyer was drunk when they filed it. Pleadings, after all, can become trial exhibits, and if your client is a self-impressed asshole, you don’t want to advertise that fact to the jury.
When you get that complaint, you share it among peers, because your friends are all litigators who love a good laugh. Had I been on the receiving end of Trump’s New York Times defamation complaint, I’d have sent it out as an early Christmas gift, evidence of the strutting incompetence of Trump’s legal team as they illegally target Trump’s political adversaries.
Trump’s complaint against the NYT chokes on its own puffery
Now that the whole world knows Trump can’t take a joke, Kimmel should deadpan deliver a few pages of Trump’s vanity suit against the NYT as his side kick Guillermo runs and hides.
Much like Trump’s embarrassing tirade at the UN this week, Trump’s defamation complaint pays cringe, fawning tribute to himself, literally citing his own “singular brilliance” and describing his 1.5% election win in 2024 as “the greatest personal and political achievement in American history.”
Eighty-five pages of Trump anointing himself begins by claiming he won “in historic fashion,” securing a “resounding mandate from the American people.” Unless you watch Fox News exclusively, you know that to be a lie. Trump’s win over Kamala Harris was less than 1.5% of the voting population, one of the smallest presidential victories in US history.
An experienced plaintiff’s attorney would have warned Trump that shooting his own credibility in the first pages is ill-advised; once juries roll their eyes, it’s hard to get them to focus.
Trump: I invented the phrase, “You’re Fired!”
Trump’s suit then whines about NYT articles that panned The Apprentice, the show that, lamentably, turned him into a household name. Trump boldly claims he invented the phrase, “You’re fired,” as if every single person ever fired prior to the year 2004 was told, as a matter of fact and law, “You’re terminated.”
Trump insists that he made The Apprentice a success— and not the other way around. He does not claim the NYT defamed him over The Apprentice, but that they groveled insufficiently over it. If anything, his complaint suggests the American people would have a legal claim against the producers of the show if it weren’t for the statute of limitations.
After his NDA finally expired, Bill Pruitt, producer of the first two seasons, was free to tell the truth. He said Trump “was not, by any stretch, a successful New York real estate tycoon like we made him out to be… We needed to legitimize Donald Trump as someone who all these young, capable people would be clamoring over one another trying to get a job working for.”
Pruitt readily admits the whole show was a con job that worked, because Trump recognized the show would “elevate his brand.” It’s also likely where Trump grew addicted to being called “Sir,” not recognizing the sarcasm of an inside joke.
Trump as the Lucky Loser
Trump’s complaint also harangues about the book “Lucky Loser: How Donald Trump Squandered His Father’s Fortune and Created the Illusion of Success” by Times reporters Susanne Craig and Russ Buettner.
Written by the authors who wrote the 2018 NYT exposé of Trump’s finances, Lucky Loser exposes how “one of the country’s biggest business failures lied his way into the White House”:
Trump spun a hardscrabble fable of how he parlayed a small loan from his father into a multibillion-dollar business and real estate empire.
This feat, he argued, made him singularly qualified to lead the country.
Except none of it was true. As his wealthy father’s chosen successor, Trump received the equivalent today of more than $500 million in family money…
One assumes defense counsel is already making oversized exhibits of Trump’s silver spoon, complete with charts and quotes.
The Judge was not amused
Last week, Republican-appointed Judge Steven Merryday struck down Trump’s $15 billion lawsuit, giving Trump’s counsel 28 days to file a version that complies with federal pleading rules.
Merryday wrote in his dismissal order that the complaint included legally improper puffery, “florid and enervating” pages lavishing blind praise on Trump while indulging his nonstop grievances. Merryday dressed down Trump’s legal team for violating pleading rules “every member of the bar of every federal court knows, or is presumed to know…”
After recounting with scorn some of the more lurid absurdities in Trump’s complaint, Merryday reminded Trump’s counsel that a complaint at law is not an ego stroke for Trump, a PR tool for Fox News or a rally speech for MAGA voters who don’t know any better.
He closed by warning counsel that if they refile the thing, the case will proceed in his courtroom in a “professional and dignified” manner—or not at all.
The joke lives on
In response to the dismissal, Trump told ABC after the ruling, “I’m winning, I’m winning the cases.” Because of course he did.
Trump’s legal team backed him up, claiming Trump “will continue to hold the Fake News accountable through this powerhouse lawsuit… in accordance with the “judge’s direction on logistics.”
The “judge’s direction on logistics,” (writer smacks the back of her own head here to dislodge her rolled eyes) is face-saving spin for the judge’s obvious smackdown: a snarly dismissal order dripping in sarcasm, 40-page limit for any re-do, and the judge’s suggestion that counsel learn civil practice rules before they come back.
Sabrina Haake is a columnist and 25+ year federal trial attorney specializing in 1st and 14th Amendment defense. Her Substack, The Haake Take, is free.