Contact? Source? Or friend? The curious connection between Michael Wolff and Jeffrey Epstein

I used to follow the author Michael Wolff religiously. The self-professed media “darling" who has spent nearly five decades writing for major media outlets like New York magazine and Vanity Fair, along with six bestselling books, claimed to know more about Jeffrey Epstein and Donald Trump than almost anyone, saying in multiple interviews that he had “upwards of 100 hours” of audio and video recordings with the notorious sex offender, in which Epstein was said to have given insider information about Donald Trump, his wife Melania, and the now-president’s comings and goings as a wealthy New York socialite with a sordid history.

My side-hustle small business is in transcription, so I wanted those interviews. They’re the holy grail of off-the-record information, and I didn’t care if it took me months and he didn’t pay me a dime: I wanted access to the inner workings of a madman. (The “devil,” as Wolff now refers to Epstein.)

Try though he might, Wolff couldn't distance himself from his relationship with Epstein. And when he segued from Manhattan media wise guy to Hamptons lifestyle influencer, complete with sockless flats and Pioneer Woman-esque backdrops in the just-so farmhouse he shares with his wife, something else started to change. He came off as resistant, boasting, dishonest and ultimately unwilling to let go of those 100 hours of interviews, no matter how many people asked, claiming that “nobody wanted them”. And when Melania Trump threatened to sue him over his claims that Epstein had introduced her to her husband, Wolff set up a GoFundMe, making over $830,000 to pay for his legal bills. But the lawsuit never happened, and in any case Wolff made $13m on his bestselling book, Fire and Fury – what did he need with a GoFundMe, backed by the nickels and dimes of middle-class subscribers?

In November, the first real set of Epstein files dropped, mostly from the Epstein 1953 estate, his private trust. In it, we saw a glimpse into Epstein’s relationships with dignitaries, friends, academics and journalists, namely Michael Wolff. Wolff has since described their interactions as “transactional” and an attempt for Epstein to shape the narrative through him. But as I began to read, it quickly became clear who was shaping the narrative, and it wasn’t Epstein. Though when asked by the Daily Beast's Joanna Coles about his "embarrassing" correspondence, Wolff blew it off as nothing more than good journalism.

In January 2026, we got our biggest batch of files, over 3 million, including 1,830 hits for “from Michael Wolff”. It was the mother lode of information, when both men completely let their guard down, never assuming their interactions would be part of one of the biggest and most controversial investigations in American history.

And so I dug in, completely invested in their off-the-record conversations, which appeared to start in 2009. But I knew there would be more. In Wolff’s own words, he’d travelled on Epstein’s private plane in the early 2000s to attend a Ted conference on the west coast. At the time he’d noticed Epstein’s propensity for “very tall girls”. It’s notable that he has since changed his statement to “model-tall young women”. But either way, it didn’t bother Wolff enough to stray from the friendship, because in 2003 he attempted to facilitate the sale of New York magazine to Epstein, Harvey Weinstein, ad executive Donny Deutsch and investor Nelson Peltz. They would ultimately be outbid by billionaire banker Bruce Wasserstein.

The emails begin in 2009, with large gaps, including the entirety of 2010 and all conversation prior. But by 2011, Epstein was sending Wolff pairs of his favourite sneakers, cementing the basis of their friendship by midsummer.

In June 2011, Wolff introduced Epstein to Ian Osborne, a young PR guy with connections, telling Epstein they could effectively wipe the internet of his sexual history in three to nine months, including “a rejiggering of search results through SEO and strategic content creation and replacement”. Over the next eight years, Wolff would add Ken Frydman, Matt Hiltzik, Oliver Lloyd and Juleanna Glover to the PR team, working day and night to bring Epstein back into the fold of wealthy society and global leaders and strategists.

But Wolff didn’t stop there, merely documenting the conversations, as he claims. By November, Epstein was sending over financial proposals, asking Wolff if he wanted to work as his full-time documentarian, a ghostwriter perhaps. Wolff responded that he was “allergic to all money discussions”, but the idea intrigued him, leading to their first on-tape interviews. By spring of 2019, Wolff was creating “counter-narratives” to the Miami Herald’s investigation into Epstein, which ultimately led to Epstein’s arrest.

But PR didn’t just mean building Epstein up; it meant discrediting any stories that came out about Epstein, his first trial, his financial dealings and the long list of accusations from minor Jane Does. When the Daily Beast began investigating Epstein in the early 2010s, Wolff offered methods of “neutralising” editor-in-chief Tina Brown, while discrediting senior investigative reporter Wayne Barrett.

When Wolff pitched a puff piece about Epstein to New York magazine in early 2015, the first draft gave Epstein everything he wanted and, topping out at 6,000 words, would make Wolff a cool $18,000.

But when Epstein read through a later draft and noticed the inclusion of his squalid sexual history – “that was added by the NYM editor (a woman)” – he began to work with Wolff to kill the project. Wolff told the magazine he was working with Epstein to make it happen, but ultimately the two men had other goals to boost Epstein’s ego and Wolff’s tax bracket.

Four weeks later, they caught wind of a new book in the works by former NYPD detective John Connolly and author James Patterson. By August, Epstein and Wolff had intercepted an email from Connolly through Epstein’s lawyers, verifying the project. And by the end of the year, just after his own book tour had finished, Wolff reached out to Patterson’s publisher. Wolff didn’t think much of either author, and, convinced the book would never happen, kept pinging the publisher for updates. He soon discovered there would indeed be a late-summer 2016 publication date via Little, Brown and Co. Epstein pushed him for updates, and he and Wolff debated whether they could publish a counter-narrative in time or soon after, something to discredit Patterson and Connolly’s take.

Wolff reached out to the publisher again, asking if he could get an advance copy of the manuscript. They agreed, probably by May, but said Wolff would need to sign an NDA to receive a copy. He did, forwarding all of the email correspondence about the book to Epstein for review. But by August, the publisher suddenly changed its mind, perhaps having picked up on Wolff’s intent and reputed friendship with Epstein.

Wolff never got an advance copy, and Filthy Rich was published on 10 October 2016, becoming a New York Times bestseller.

Wolff has built a platform on being a journalist, an author and a purveyor of insider information about Epstein and Trump. But what became clear to me reading these 1,000-plus pages of Department of Justice files was that he often set aside the writer in order to be the confidant, and, more realistically, the close friend. Now, we can argue if this was strategy or not, but nearly 20 years later, it’s a rough sell to say he was there to write a few articles.

In one of Wolff’s more wordy counter-narratives, he uses his lengthy friendship with Epstein as a kind of character reference to connect him with Bill Gates, a highly-sought-after power-friendship Epstein worked on for years.

“I think the best way to approach it is … my friendship with you – how we met; ten years of knowing you; our chats; and the ways in which that shows you to be inherently unique and interesting.”

But their close friendship took them all over the world, namely to Epstein’s properties in New York, Palm Beach and Paris, where Wolff often travelled with his young wife, former Daily Beast intern Victoria Floethe. Epstein invited Wolff to come to Little Saint James, his notorious island in the Caribbean, but it’s not known whether Wolff ever followed through.

Over the course of their 20-year friendship, Wolff fed into Epstein’s argument that he was innocent, that his buddy Woody Allen was framed, and that he simply liked a “rub-and-tug” from adult women every once in a while, and what’s the big deal? Meanwhile, Wolff enjoyed the intel, meeting Epstein’s bigger connections and hobnobbing with New York’s wealthy elite.

With Epstein’s first trial in the rear-view mirror, Wolff had no problem recommending a young “girl I know,” a graduate student from Columbia, to apply as Epstein’s new assistant. And when leaked information about Epstein hit the media, Wolff recommended he pay off his doorman, the likely leaker. And those Melania transcripts? The stuff Epstein allegedly had on New York Times chairman “Pinch” Sulzberger? Those conversations would be held offline, perhaps in 100 hours of recorded interviews. As Wolff bounced back and forth to the White House, gathering quotes from Donald Trump and the cabinet for Fire and Fury, Epstein added anecdotes, read drafts, and edited to his liking.

But the biggest and most beneficial connection to both men, with an equal hatred of the now-president of the US, was Steve Bannon, whom Wolff referred to as “spectrumy” and unfocused, always late and paranoid. And yet, more than Wolff, Bannon seemed to know the most and have the most concrete connections with Trump’s inner circle. And thus Wolff introduced Bannon and Epstein in October 2017 – a friendship that would last until Epstein’s death.

It played out rather curiously – a kind of choreography of back-stabbing, distrust and competitive lunches to determine who among the three were the closest. Wolff even used his interviews with Epstein as leverage to get Bannon to talk. And talk he did. When Fire and Fury was released in January 2018, it was clear Wolff, at least for the moment, had won.

Most people became friends with Epstein for three reasons: money, women and connections to important people. I’d argue that the third fuelled the first two, but it certainly was the most enticing for someone like Wolff. And Epstein would not disappoint. He offered to introduce Wolff to former Israeli prime minister Ehud Barak, Woody Allen, Peter Thiel, Larry Summers, Gordon Brown, Sultan bin Sulayem, Leon Black, Ken Starr, Deepak Chopra, Noam Chomsky, James Watson, Ariane Rothschild and Joi Ito. He also invited Wolff to several “UN dinners” with representatives from Mongolia, Qatar, Kuwait and Saudi Arabia, and also to discuss crypto, AI, mathematics and quantum computing. Wolff rarely said no.

But on one particular occasion, Wolff’s eagerness to connect crossed ethical, and potentially legal, lines. In March 2017, Epstein offered to take Wolff to meet with a small group of Saudi leadership, led by someone with the initials “STD.” The Saudis were paranoid, “under close watch”, Epstein said, and would only meet in New York. Wolff agreed, saying he would “share with them all [he knew] about [White House] operation … 100% off the record.” Wolff knew a lot about White House operations, having spent many hours in the Oval Office with Trump prepping Fire and Fury. He’d spoken with officials and cabinet members in up to 200 separate interviews, including Jared Kushner and Stephen Miller, two of Trump’s closest strategists.

Two years later, Epstein offered insider information into the results of the Mueller investigation. And when Wolff asked for insights into the Panama Papers in 2016, Epstein replied: “I’m your man.” It was clear both men had connections.

As we watched the two men dodge the #MeToo Movement with quiet expertise and a whole lot of PR and financial backing – “cross your fingers”; “believe you me, I do” – it’s hard to ignore how much Wolff would have gleaned from nearly 20 years and 100 hours of interviews as Epstein’s closest confidant. Whether it was riding on private planes with “tall girls”, hiring young assistants, meeting with Juilliard students in Epstein’s home, or endlessly conspiring to take down Dylan Farrow and recreate Woody Allen’s history as a “love story”, Wolff’s intent was clear: he wasn’t in it for survivors.

And when Wolff claimed to have seen “roughly a dozen” photos of Trump from Epstein’s safe that dated back to the 1990s, with “topless young women” and a “telltale stain,” there is no record that he reported anything to authorities. Meanwhile, he used the information to write a best-selling book about Trump, making $13m with Epstein’s help.

Just prior to Epstein’s arrest in July 2019, Wolff and Epstein had been discussing Wolff’s next project, a book about Epstein’s life. But not about what we know now, or what we might want to read while we pursue the arrest and conviction of a long list of co-conspirators who perpetrated a sex-trafficking ring on hundreds of underage girls. Instead, the two men had begun preparing a glowing review of Epstein’s return to glory, complete with his contributions to science and academia, global finance, Hollywood, and plans for a new mental health centre for sex workers named after one of his own survivors, Courtney Wild.

And while Bannon quietly interviewed Epstein for a small documentary of his own, Wolff connected Epstein with a high-cost cinematographer and the two men got to work on a documentary with big names like Woody Allen, James Watson, Noam Chomsky and Tim Zagat – “all eighties and above, should be spoken to sooner rather than later”.

The only conclusion I can reach about Michael Wolff is that he was in it for himself. And the platform he’s been given now to “out” his buddy Epstein is one of hypocrisy and even cruelty toward the women he ignored, steamrolled and discredited in the name of glory. It was all to write stories and make closer connections with Epstein’s vast rolodex, clearing a path for future books about the “real villain”, Donald Trump.

With 1,830 pages in the DoJ files documenting the relationship between Jeffrey Epstein and Michael Wolff, I call on Congress to investigate those 100 hours of interviews, and any half-finished book or project Wolff was working on when Epstein died in 2019. Because I don’t believe that he hung on to them because “nobody wanted them”. I don’t even think it’s for money at this point, because he could put everything behind a paywall and click “publish”. No. I think those interviews not only condemn Epstein and Trump, but I think they condemn Michael Wolff. And now that we see who he really is, the risk is too great to make them public.

Because a co-conspirator doesn’t have to be the money guy. It doesn’t have to be the pimp. If you asked Al Capone, the greatest asset was always a journalist.

You can read all of Michael Wolff’s emails to Jeffrey Epstein here

Or, if you prefer a more searchable database, you can find one here, prepared with help from Rye Howard-Stone

This is an edited version of a post on Ellie Leonard’s Substack The Panicked Writer