In 2003 David Carr, the New York Times’s late, great media columnist, disclosed a $50m bid to buy New York Magazine that had been orchestrated by the writer and journalist Michael Wolff.
Among the big hitters whom Wolff helped assemble for the deal was the billionaire media tycoon Mort Zuckerman, the not-yet-convicted sex offender and Hollywood mogul Harvey Weinstein, and the not-yet-convicted sex trafficker and financier Jeffrey Epstein.
The deal never came off. But it was illuminating for what it revealed about Wolff’s own journalistic ambitions.
Wolff told Carr that he hoped the sale would go ahead because it would give New York Magazine, through its new owners, “incredible, undreamed-of access to the kinds of circles that it should be a part of”.
Such a blurring of the lines between journalism and its subject matter – the aim being to be “part of” rich and powerful circles, not just report on them – was classic Michael Wolff.
This week the world got a glimpse of just how far the bestselling author has been prepared to go in blurring those lines in pursuit of access. Among the documents released by congressional Democrats from Epstein’s estate on Wednesday were email exchanges between Wolff and the disgraced financier and pedophile who killed himself in jail in 2019 as he faced trial on sex-trafficking charges.
One of the email threads, dating from 15 December 2015, bore the subject line: “Heads up”. In it, Wolff warned Epstein that later that day, at a televised debate for the Republican presidential primary, Donald Trump was likely to be quizzed about his years-long social relationship with the financier.
By then, Epstein had pleaded guilty in Florida to solicitation of prostitution with a minor. Though Trump has always claimed they had fallen out years earlier, their association remained – as it still does today – politically problematic for him.
Epstein responded to Wolff’s alert by asking for personal advice. “If we were able to craft an answer for him [Trump], what do you think it should be?” he wrote.
Wolff replied: “I think you should let him hang himself. 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.”
This is not the stuff of journalistic codes of conduct. Reporters, as a general rule, are not encouraged to give strategic PR advice to public figures about whom they might be writing, whether or not their interlocutor is a convicted sex trafficker.
Social media lit up after the release of the emails with arch commentary on Wolff. The independent journalist Isaac Saul said the author had been “literally game planning with Epstein about how to defend himself in the media. This is journalism?”
Brian Reed, host of a podcast on journalism, Question Everything, asked: “WTF is going on here with Michael Wolff giving PR strategy to Jeffrey Epstein?”
The Guardian reached out to Wolff for this article but he did not respond. He told CNN on Wednesday that he could not remember the context of the newly released email exchanges with Epstein.
He added: “I was engaged then in an in-depth conversation with Epstein about his relationship with Trump and this seems to be part of that conversation.”
Wolff’s sparse explanation does little to address the whiplash unleashed by the newly disclosed emails. It’s fair to say, though, that Wolff has never been much flustered by complaints around his journalistic ethics.
His many gossipy, behind-the-scenes exposés of the big beasts of politics and business – not least Trump himself – have invariably kicked up the dust the writer craves, but they have also been often criticised for their casual approach to factchecking.
Maggie Haberman, the New York Times political reporter, has argued that such insouciance towards fact is intrinsic to Wolff’s writing. “He believes in larger truths and narratives,” she told CNN when Wolff’s first and most incendiary volume on Trump’s White House, Fire and Fury, came out in 2018. “So he creates a narrative that is notionally true, that’s conceptually true; the details are often wrong.”
Ben Smith, editor-in-chief of the news site Semafor, told the Guardian that Wolff quite consciously steps outside the bounds of conventional journalism. “He considers himself a writer, not a journalist. He has never played by the rules of American newspaper journalism.”
Not playing by the rules has in large measure been the key to his success. In 2021, Smith profiled Wolff for the New York Times and was given clues by the author as to how he plies his controversial craft.
Wolff gains the trust of his powerful and wealthy subjects, he told Smith, in part because he himself goes into “a bit of a Walter Mitty trance that he could be living their lives, something they can sense and appreciate”.
Over the past two decades, Wolff has turned that Walter Mitty guise – that projection that he wants to be “one of them” – into a journalistic conveyor belt. He has used it to fill a stream of gossip-laden and what Carr called “joyously nasty” magazine articles and a dozen books, including four Trump bestsellers.
The pattern is the same. He cosies up to powerful men in politics and finance, gains exceptional access to them, then produces insider accounts – often with explosive force, and often to the subjects’ discomfort if not dismay.
Rupert Murdoch sat down with Wolff for more than 50 hours of interviews for the 2008 book The Man Who Owns the News, even arranging for his then 99-year-old mother in Australia to talk to the author. Shortly before the book came out Murdoch obtained a copy of it, and complained that it contained “some extremely damaging misstatements of fact”.
Steve Bannon, the rightwing provocateur, gave Wolff exceptional access to the West Wing in the initial flush of Trump’s first presidency, during which the writer was allowed to wander around freely, entirely unchaperoned. The then White House chief strategist inexplicably shared with Wolff many caustic remarks about the president’s family, including the memorable line that Ivanka Trump was “as dumb as a brick”.
Fire and Fury led to Bannon’s estrangement from Trump, who said his former confidant had “lost his mind”, and helped send Bannon into the political wilderness. (He has since regained his Maga perch and, also inexplicably, continued to talk to Wolff for subsequent volumes.)
As for Trump and Wolff, there is little love lost there. Steven Cheung, the current White House communications director, has a mantra about Wolff which he regularly blasts out to reporters: “Michael Wolff is a lying sack of shit and has been proven to be a fraud.”
Back in 2018, Trump tried to stop publication of Fire and Fury. The president sent a cease-and-desist letter to the publisher – a vain effort that merely boosted the book’s sales and Wolff’s bank balance.
It is one of the mysteries of Wolff’s endurance that his uber-powerful subjects never seem to learn from past mistakes – their own or others’. Melania Trump is now repeating her husband’s attempt to silence the writer.
Last month the first lady’s lawyer wrote to Wolff threatening to sue him for more than $1bn for the “overwhelming reputational and financial harm” he had caused her. The letter objected to comments made by Wolff on the Daily Beast podcast he co-hosts, Inside Trump’s Head, in which he suggested that she was heavily involved in the White House handling of the Epstein scandal.
Melania Trump’s office accused Wolff of spreading “malicious and defamatory falsehoods” and of seeking “undeserved attention and money” from his “unlawful conduct”.
Wolff has fired back by suing the first lady, on grounds that she is attempting to create a climate of fear to shut down his reporting on Epstein. The author has clearly hit a public nerve – the GoFundMe page he set up for the legal action has attracted more than 15,000 largely small donations totaling more than $700,000.
Wolff says the money will be used not only to cover legal costs but also “for all of us to see behind the dark curtain of the Epstein affair”. Which brings us back to his connection with Epstein and the blurring of those journalistic lines.
By Wolff’s own account, he met Epstein in the late 1990s when he was flown on the financier’s jet to the west coast to attend a conference. Even at that first meeting, it was clear to Wolff there was something unusual afoot, as Epstein was accompanied by three teenage girls.
“You didn’t know what to make of this … Who is this man with this very large airplane and these very tall girls?” Wolff said years later.
Soon after that first meeting, Wolff was invited to tea at Epstein’s Manhattan town house, and occasional contact continued between them from then on. When the financier began to face legal scrutiny – he was first criminally investigated for sexually abusing underage girls in 2005 – Wolff was already quick to offer advice on how he should present himself.
In December 2007, by which time Epstein was under indictment in Florida, Wolff gave an interview to New York Magazine in which he described a conversation with the financier. “At one point, when his troubles began, he was talking to me and said, ‘What can I say, I like young girls.’ I said, ‘Maybe you should say, ‘I like young women.’”
By 2017, with Trump now in the White House, Wolff’s contact with the convicted sex offender turned into a more formal journalistic arrangement. Epstein, according to Wolff, wanted him to write his biography, while Wolff wanted to extract details of Epstein’s longstanding friendship with Trump for use in Fire and Fury.
The two men sat down for what Wolff has said were more than 100 hours of recorded discussions. The author recalled those long conversations in a podcast released just days before last November’s presidential election.
The interviews were conducted either at Epstein’s dining table or in the huge study that ran the entire length of his baronial East 71st Street town house. Once again, decades after Wolff’s first puzzling encounter with Epstein accompanied by three teenage girls onboard his jet, the circumstances were peculiar.
“There were always a background of girls at Epstein’s house,” Wolff said. “I never thought any of these girls were necessarily underage, none of them did seem to be underage, they were a kind of cast of characters. I had no idea what they did other than provide this backdrop to this hedonistic lifestyle.”
For a leading chronicler of power and fame in the modern age to show such little journalistic curiosity about the actions of a convicted sex offender months away from federal arrest encapsulates the Wolff conundrum. Why would he turn a blind eye to such a glaring “backdrop”?
The most likely explanation is that Wolff’s desire for Epstein’s insider’s dope on Trump outweighed any concern for his source’s own wrongdoings. This week the extent of that Faustian bargain in pursuit of a good story was revealed.
