Every president deserves to have a nemesis in the press. There was Benjamin Franklin Bache (grandson of), founder of the Philadelphia Aurora, who criticized John Adams so much that he was arrested for sedition. Nixon had Jack Anderson, a “son of a bitch” columnist so problematic that the White House plotted his assassination. And while Donald Trump has a crowded field to pluck from, his nemesis might just end up being Michael Wolff.
More than almost any other writer—more so even than any former Trump staffer—Wolff has made his name by being a thorn in the president’s side. He has written four books on Trump in the last decade alone, the first of which, Fire and Fury, dominated the global news agenda for months. But it is only now that the pair look set to square up for good.
To précis the situation, earlier this year several commenters and outlets alleged links between Melania Trump and Jeffrey Epstein. Trump’s lawyers denied the allegations and reacted with blanket legal threats across the board, prompting apologies from James Carville and the removal of passages from Andrew Lownie’s unauthorized Prince Andrew biography.
The Daily Beast also retracted and apologized for a report headlined “Melania Trump ‘Very Involved’ in Epstein Scandal: Author,” based on recordings that Wolff had made with Epstein, in which Epstein alleged that the Trumps first had sex on his “Lolita Express” plane.
Trump’s lawyers threatened Wolff with the same thing, suggesting that he’d be sued for a billion dollars for noncompliance. Rather than acquiescing, Wolff has turned around and sued Melania, in the hope that he’ll get the Trumps on the stand under oath.
Thrillingly, Wolff’s filing is just about as gleefully two-footed as these things get. Explicitly claiming that Trump and his “MAGA myrmidons” are threatening critics with lawsuits in order to “extract unjustified payments and North Korean style confessions,” the 17-page document goes on to regurgitate almost every claim made against Donald and Melania Trump in regard to Epstein. It includes the Epstein allegation that “Trump liked to ‘f– his friend’s wives,” describes the Trump marriage as both a “trophy” and a “sham,” and declares it “proper to inquire” about what Trump and Epstein did during their “10 years of pursuing models, including super models, runway models, catalog models, Eastern European models, and girls who just dreamed of being models.”
If nothing else, in an age where institutions often flinch at Trump’s legal aggression, it’s exciting to see someone play Trump at his own game. The mistake Melania made seems to be that Wolff is a lot more like her husband than either party would care to admit.
Both figures, clearly, have a flair for the theatrical. Both have had brushes with public sex scandals. (In 2009, Wolff’s now wife, Victoria Floethe, wrote a piece for The Spectator reflecting on the reaction to their affair.) And both resort to unorthodox methods to get their point across.
Nowhere was this more clear than in Fire and Fury, in which Wolff reported the chaos of Trump’s first term by plonking himself down on a West Wing couch for an extended period of time—and on semi-authorized terms, to boot—and detailing whatever happened in front of him. The book became an instant sensation, the definitive document proving that nobody in charge had any idea what they were doing.
Trump and Wolff also share a complicated (to put it mildly) relationship to the truth. Trump’s vagaries in this regard are well known, but similar claims have dogged Wolff’s career. After the publication of his 1998 dot-com memoir, Burn Rate, 13 people claimed that Wolff had “invented or changed quotes” attributed to them, according to Brill’s Content. Similarly, Fire and Fury ended up undermining its own authority with inaccurate or disputed claims. For example, Wolff allegedly confused a journalist with a similarly named lobbyist and got a number of dates wrong; and Anna Wintour rejected his assertion that she had pushed Trump for a role as U.K. ambassador.
Viewed in this way, a collision course between Trump and Wolff seems inevitable. Especially because, as Wolff contends, Melania’s initial threat was an attempt to force him to back away from his fifth book. And that book, it is thought, will be about the relationship between Trump and Epstein.
Wolff says that he conducted approximately 100 hours of interviews with Epstein before he died, interviews which threaten to delve deeper into Epstein and Trump’s relationship than anything ever before. Wolff has already teased the existence of the recordings, even going so far as to post audio of one clip—in which Epstein repeats the allegation about Trump enjoying sex with his friends’ wives, while offering up that Trump “probably had a scalp reduction” to combat his baldness—on his Bluesky account.
What happens now is a game of Who Blinks First. The Trumps have shown that they have the money to pursue their enemies through the courts—it’s likely that Wolff will have to crowd-fund his lawsuit, despite the reported millions his career has earned him—but they certainly won’t relish the thought of having to defend themselves on a subject as touchy as this. Either way, whatever happens, Wolff’s next blockbuster seems all but guaranteed.
Stuart Heritage is a Writer at Large at AIR MAIL. He is the author of Bald: How I Slowly Learned to Not Hate Having No Hair (And You Can Too)
