Why Trump Won’t Stop Suing the Media and Losing

Why would the most notoriously cash-strapped man in America waste money on frivolous lawsuits?

On Monday, Donald Trump—whose lawyers recently announced that he can’t come up with the money to post a $454 million bond in his civil fraud case—fired off yet another suit against a news organization that reported facts he didn’t like. The targets this time are ABC News and its anchor George Stephanopoulos, who Trump alleges defamed him by stating that Trump had been found liable for raping E. Jean Carroll.

The case looks like a sure loser. Trump was technically found liable under New York law for sexual abuse, not for rape, but the judge in the civil case ruled that, by forcibly penetrating Carroll’s vagina with his fingers, “Mr. Trump in fact did ‘rape’ Ms. Carroll as that term commonly is used and understood.” But no matter. The Stephanopoulos suit slots into a well-worn groove for Trump, who for years has lodged periodic lawsuits against alleged purveyors of “fake news” about him. Targets have included The Washington Post, The New York Times, CNN, Bob Woodward, and a Wisconsin TV station that ran an attack ad against him during the 2020 campaign. Trump has even gone after the board of the Pulitzer Prizes for awarding Pulitzers to the Post and the Times for their coverage of his connections to Russia.

Filing these suits has been costly for Trump—or rather, for donors to his campaign and affiliated political action committees, who have footed millions of dollars in legal fees. Not one of Trump’s media lawsuits has ever succeeded, nor is one ever likely to, given both the underlying facts and the towering bar a president or former president faces in proving defamation. In one case against The New York Times, a judge found Trump’s argument so flimsy that he ordered Trump to pay the Times’ legal fees. In other cases, such as the one involving the Wisconsin station, the suit was quietly withdrawn a few months after it was filed.

[David A. Graham: Trump’s money problems are very real and very bad]

So why does he keep doing it? On a basic level, this appears to be just Trump being Trump—peevish, headstrong, and narcissistic. For decades, his love-hate relationship with reporters has tended to flare into legal action, as it did in 2006 when he sued the writer Tim O’Brien over a few pages in a book that questioned Trump’s personal wealth. As Trump told me in an interview in 2016, he knew he couldn’t win that suit (he didn’t) but brought it anyway to score a few points. “I spent a couple of bucks on legal fees, and [O’Brien’s publisher] spent a whole lot more,” he said then. “I did it to make his life miserable, which I’m happy about.”

But Trump’s quixotic legal crusades are not as irrational as they appear. Suing the press serves as a branding exercise and a fundraising tool. The lawsuits show his supporters that Trump is taking the fight to those lying journalists—so won’t you contribute a few dollars to the cause? They thus have become an end unto themselves, part of an infinite loop: sue, publicize the suit, solicit and collect donations, sue again. The cases may be weak on the legal merits, but they “further his narrative of being persecuted by the radical left media,” Brett Kappel, a campaign-finance lawyer who has researched Trump’s legal actions against the press, told me.

This narrative has been a fixture of Trump’s fundraising pitches for years. A few weeks after his inauguration, in 2017, one of his fundraising committees sent out an email urging donors “to do your part to fight back against the media’s attacks and deceptions” by sending contributions that would help “cut through the noise” of news reports. Even before Trump filed a lawsuit against CNN in August 2022 (for describing his election lies as “the Big Lie”), his campaign was using the nonexistent suit to drum up contributions. “I’m calling on my best and most dedicated supporters to add their names to stand with me in my impending LAWSUIT against Fake News CNN,” read a fundraising email. A second email sent out under Trump’s name a few hours later struck a sterner tone: “I’m going to look over the names of the first 45 Patriots who added their names to publicly stand with their President AGAINST CNN.”

When Trump got around to filing the suit two months later, the appeals began anew. “I am SUING the Corrupt News Network (CNN) for DEFAMING and SLANDERING my name,” the campaign email read, in a chaotic typographical style reminiscent of a ransom note. “They’ve called me a LIAR, and so far, I’ve been proven RIGHT about EVERYTHING. Remember, when they come after ME, they are really coming after YOU … I’m calling on YOU to rush in a donation of ANY AMOUNT RIGHT NOW to make a statement that you PROUDLY stand with me.” The suit was dismissed last year by a federal judge appointed by Trump. Trump is appealing.

Of course, the cost of suing news organizations is a pittance compared with what Trump’s donors are spending on his criminal defense. But it isn’t cheap. According to Federal Election Commission records culled by Kappel, the Trump-controlled Save America PAC shelled out nearly $500,000 to the firm that sued the Pulitzer Prize board on Trump’s behalf in 2022. It paid $211,000 last year to another law firm that handled Trump’s litigation against CNN, among other matters, and an additional $203,000 to the firm handling the appeal.

The biggest recipient, by far, has been the attorney Charles Harder, the defamation specialist who represented Hulk Hogan in his successful suit against Gawker Media in 2016. From early 2018 to May 2021, according to FEC records, Harder took $4.4 million in fees from Trump-affiliated organizations. At one point in 2020, Harder’s Beverly Hills firm received more money than any other firm doing work for Trump.

[From the January/February 2024 issue: Is journalism ready?]

Harder’s work on Trump’s behalf didn’t produce anything close to his career-making Hogan verdict, which resulted in a $140 million award that drove Gawker into bankruptcy. Harder took the lead in Trump’s effort to suppress publication of Michael Wolff’s book Fire and Fury in 2018; he sent cease-and-desist letters to Wolff and his publisher, Henry Holt and Co., before the book’s release, claiming that it contained libelous passages. The book was released as scheduled and became a best seller, and Trump didn’t sue. In 2020, Harder handled Trump’s lawsuit against the Times, alleging that an opinion piece by the former Times editor Max Frankel was defamatory. A judge dismissed that suit in 2021. (Harder, who no longer represents Trump, declined to comment for this story.)

Whether Trump’s beat-the-press strategy is a net financial winner, once all the donations are collected and the attorney fees are subtracted, is hard to say. But Trump’s filing of another hopeless lawsuit this week suggests that the math may be in his favor. Why bother paying lawyers millions of dollars to sue and appeal if the return on investment is less than zero? Trump may be petty and irrational, but he has never been accused of neglecting his own financial interests. (A Trump spokesperson didn’t return a request for comment.)

At the moment, of course, Trump has much bigger headaches. As of this writing, he’s days away from having his assets seized to satisfy that civil-fraud judgment. His overall fundraising has lagged President Joe Biden’s. And he is burning through his supporters’ money to pay for his criminal defense. Despite all that, he still finds a way to keep filing lawsuits against the media. You almost have to admire the commitment.