Trump’s latest lawsuit is hilarious—until it isn’t
President Donald Trump has sued another major media outlet, this time The New York Times for libeling him with slander, or … something. But hey, one of his lawyers in the lawsuit is Alejandro Brito, so you know this thing will be concise, levelheaded, and airtight.
Wait, wait—we’re getting word that this suit actually looks like this.
As a threshold matter, it does not take a lawyer to understand that this is not an actual complaint. It’s partly an extended bout of whining, partly an extortion attempt (Trump wants $15 billion in damages), and partly Trump trying to tee up a case for the Supreme Court to overturn New York Times v. Sullivan, the landmark defamation case that theoretically protects the media against just this kind of sham lawsuit.
And this suit is 85 pages long. It contains multitudes. The second page contains a screenshot of the 2024 electoral map, apparently taken on a phone. Not sure why that’s in here, except that Trump seemingly cannot stop himself from boasting about it. Indeed, the lawsuit makes sure to tell you right away how Trump’s team feels about his 2024 win: “With the overwhelming victory, President Trump secured the greatest personal and political achievement in American history.”
Does Trump’s team think no one has ever been elected to the presidency twice? Do they see his victory as a bigger achievement than, say, ending the Civil War? As bigger than founding the nation? Bigger than Ronald Reagan’s actual blowout victory in 1984?
They probably do.
Eventually, the lawsuit addresses one of the Times’ filthy lies: “The [Editorial] Board asserted hypocritically and without evidence that President Trump would ‘defy the norms and dismantle the institutions that have made our country strong.’”

First, that’s not defamatory. It is an expression of pure opinion. Did they not teach that at wherever Brito and his friends went to law school?
But the point of the lawsuit doesn’t appear to be making a compelling legal argument, especially not when it literally claims, with no irony, that Trump has “sui generis charisma and unique business acumen.” Trump’s lawyers are right about the “unique” part since it does take a special kind of business acumen to bankrupt multiple casinos.
The lawsuit contains an entire section on how unfair it was for the Times to characterize Trump’s former TV show “The Apprentice” as producer Mark Burnett rescuing Trump from a slow, sad slide into irrelevance and turning him into a superstar instead. Setting aside that this is what happened, it’s still not defamation of any sort.
The real meat of this lawsuit is that Trump wants NYT v. Sullivan overturned, and you know in the mosquito-laden fever swamp that is Trump’s brain, he surely thinks it would be neatly symmetrical if he could get rid of that ruling … by suing The New York Times. Genius move, sir.
The lawsuit continues: “Contrary to the Times’ and its reporters’ apparent impression, the First Amendment has never furnished the Times—or Penguin, or anyone else—with an unqualified privilege to make false, malicious, and defamatory statements about its opponents in order to try and ruin their lives and livelihoods. President Trump brings this suit to highlight that principle and to clearly state to all Americans exhausted by, and furious at, the decades of journalistic corruption, that the era of unchecked, deliberate defamation by the Times and other legacy media outlets is over.”
You see, America? He’s doing this for all of us! Not just for himself and his pals who want to sue publications into oblivion unless they become house organs for the regime, basically.
Sadly, Trump already has a few friends on the Supreme Court who agree with him that NYT v. Sullivan should be revisited.
Another big chunk of this lawsuit is Trump’s lawyers patting themselves on the back for helping Trump extort other media outlets:
President Trump’s transcendent ability to defy wrongful conventions has been vividly reflected in his successful undertaking to restore integrity to journalism, and repair the immense damage caused by legacy media outlets such as the Times for the better part of a decade. These legal victories were so significant that even the Times had no choice but to, at last, reverse their position, and reluctantly recognize the importance of the President’s highly meritorious and successful cases.
It takes a minute before you realize that what Trump’s lawyers are bragging about here is the settlements they have extorted from other mainstream media outlets. But maybe his lawyers skipped the infinite days of law school where they explain that settlements are not victories but instead, well, settlements.
It’s also genuinely weird to brag about previous successful extortion efforts in a lawsuit seemingly designed to extort The New York Times.

This thing is so bad that even mainstream outlets like CNN are like Come on, man.
“The 85-page suit reads at times like a pro-Trump op-ed, with page after page of gushing praise for the president and repeated references to lawsuits he has filed against other media outlets. Media lawyers immediately expressed skepticism about Trump’s chances of prevailing,” CNN wrote in their article on the lawsuit.
Of course, it doesn’t matter much what this lawsuit looks like. Trump’s lawyers are not really acting as lawyers. Rather, they’re functioning as enforcers willing to attack any media company that makes Trump sad. To Trump and his team, writing anything negative about him should essentially be illegal.
What this complaint ultimately shows is the extreme foolishness of seemingly letting your client write it, especially if your client is a self-aggrandizing, thin-skinned madman who happens to be president. But the lawsuit’s overall crappiness isn’t the point. This is now just the way Trump opens negotiations with media companies: suing them based on lies, demanding billions, and hoping they buckle.
Sigh. The Times will probably buckle.