Michael Wolff, a writer, reporter, columnist, author and would-be mogul, has spent his long career building his profile as an insider with gossip on New York luminaries, while sometimes drawing scrutiny from other journalists.
That profile expanded on Wednesday: Mr. Wolff, it turns out, has been enough of an insider that he once provided advice to Jeffrey Epstein, the disgraced sex offender, on how to handle his dealings with Donald J. Trump, who was running for president at the time.
That revelation emerged from emails between Mr. Wolff and Mr. Epstein released by Washington lawmakers, shedding new light on the relationship between the two.
In one of the emails, from December 2015, Mr. Wolff said CNN planned to ask Mr. Trump about his relationship with Mr. Epstein, and then counseled Mr. Epstein on next steps.
“I think you should let him hang himself,” Mr. Wolff wrote. “If he says he hasn’t been on the plane or to the house, then that gives you a valuable PR and political currency. You can hang him in a way that potentially generates a positive benefit for you, or, if it really looks like he could win, you could save him, generating a debt.”
In October 2016, Mr. Wolff sent Mr. Epstein an email saying there was an “opportunity to come forward this week and talk about Trump in such a way that could garner you great sympathy and help finish him.” The exchange came late in Mr. Trump’s first presidential campaign, and weeks after a recording of Mr. Trump making vulgar comments about women to an “Access Hollywood” host emerged.
Before the 2024 presidential election, Mr. Wolff disclosed that he had interviewed Mr. Epstein “periodically” for his 2018 book, “Fire and Fury: Inside the Trump White House,” which rocketed to the top of best-seller lists with its depiction of a chaotic White House and key officials criticizing the president.
In 2019, Mr. Epstein was charged in a federal indictment with sex trafficking of minors; he was subsequently found dead in a cell at a federal detention center in Manhattan. The authorities concluded that he had died by suicide. The case against Mr. Epstein, and the circumstances of his death, fueled years of speculation about his relations with top figures in American politics and business.
Given the public interest in Mr. Epstein, Mr. Wolff released tapes of his interviews with the convicted sex offender shortly before the 2024 presidential election.
“I would say I had a dozen meetings, maybe a dozen and a half meetings, with various outlets, and everybody was interested — everybody was listening, there were a lot of executives in rooms or on Zoom calls — and then everybody passed,” Mr. Wolff said in an interview with James Surowiecki in The Yale Review.
The Daily Beast published an exclusive on the tapes.
The latest revelations speak to a well-established reality of recent decades: Journalists’ communications have a way of coming back to haunt them. WikiLeaks released hacked emails from Democratic operatives in 2016, bringing to light the transactional nature of high-profile Washington reporting. Texts and emails that surfaced in a voting company’s defamation suit against Fox News showed that high-ranking network officials disbelieved misinformation about the 2020 election that appeared on the cable channel.
Also included in the email release is correspondence between Mr. Epstein and Landon Thomas Jr., a New York Times reporter who left the paper in early 2019. A spokeswoman for The Times said Mr. Thomas had left the company “after editors discovered his failure to abide by our ethical standards.”
Mr. Thomas said in an interview on Wednesday that Mr. Epstein had been a “longstanding and very productive source” for him.
In Mr. Wolff’s case, the freshly released material suggests extraordinary coziness between journalist and source. “This is not his job,” said Edward Wasserman, a professor of journalism at the University of California, Berkeley. “He’s becoming a participant, a player and a shaper of the news he’s going to report on.”
Mr. Wolff, 72, did not immediately respond to a requests for comment for this article. In comments to ABC News, he said that he couldn’t remember the specifics of the email exchange but that he had been having discussions with Mr. Epstein about his relationship with Mr. Trump. The goal, he said, was to get Mr. Epstein to go public with his comments about Mr. Trump.
And in an Instagram post, Mr. Wolff acknowledged the emails between himself and Mr. Epstein and argued that the story of Mr. Trump’s relationship with Mr. Epstein was “central to our time.” The pre-election release of his Epstein tapes, Mr. Wolff lamented in the post, had “little effect.”
In October, Mr. Wolff sued Melania Trump, whose counsel had sent Mr. Wolff a letter accusing him of defaming her and threatening legal action for more than $1 billion in damages.
“Mrs. Trump’s claims are made for the purpose of harassing, intimidating, punishing or otherwise maliciously inhibiting Mr. Wolff’s free exercise of speech,” Mr. Wolff’s complaint noted. In his Instagram post on Wednesday, he said he thought his lawsuit would enable him to press both Mr. Trump and Mrs. Trump about Mr. Epstein.
Mr. Wolff has written several books on Mr. Trump and published his shorter fare in Vanity Fair, The Hollywood Reporter, New York magazine and other outlets. The often eyebrow-raising details in his reporting have long drawn criticism for his tactics. In a 2004 piece in The New Republic, Michelle Cottle wrote that “the scenes in his columns aren’t recreated so much as created — springing from Wolff’s imagination rather than from actual knowledge of events.”
His “Fire and Fury” book in 2018 found an enormous audience among Mr. Trump’s detractors and fact checkers, who cited a number of errors in his reporting. Though some of the concerns were small, a bigger one emerged as Mr. Wolff made the promotional rounds on television.
On the HBO show “Real Time With Bill Maher,” Mr. Wolff said Mr. Trump was currently having an extramarital affair. Though he declined to name the paramour, he gave Mr. Maher’s audience a hint, saying the telling passage was toward the end of the book. “Now that I’ve told you, when you hit that paragraph, you’re going to say, ‘Bingo.’”
Mr. Wolff appeared to be referring to a portion of the book detailing the relationship between Mr. Trump and Nikki Haley, who was serving as U.S. ambassador to the United Nations. Ms. Haley denied having an affair with Mr. Trump and called the speculation “disgusting.”
In a 2019 interview with The Times, Mr. Wolff said: “As a journalist — or as a writer — my obligation is to come as close to the truth as I possibly can. And that’s not as close to someone else’s truth, but the truth as I see it.”
Jessica Silver-Greenberg contributed reporting.
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