American financier Jeffrey Epstein (left) and Donald Trump pose together at the Mar-a-Lago estate, Palm Beach, Florida, in 1997. Photo / Getty Images
“I have been beating this horse for a very, very long time,” says Michael Wolff.
“And suddenly now everybody’s [saying] ‘Oh yeah, Donald Trump and Jeffrey Epstein’. Why people did not see that this was a story a long time ago is just amazing to me. It is confusing that it could have been out there in plain view, and ignored for so long.”
Five years before Epstein’s death in 2019, Wolff, best known as the author of four bestselling books on Trump’s presidency, began recording hundreds of interviews with the financier, and attended exclusive events at his flat in New York. For years, no publisher or broadcaster has dared to touch the explosive cache, which he claims runs close to 100 hours of tape, split over some 30 sessions together.
Instead, Wolff has released only snippets of the recordings to date. But now, thanks to the mounting speculation about the extent of Trump’s relationship with Epstein, the tapes have become some of the most in-demand material in America.
Epstein died by suicide while awaiting trial for sex trafficking, accused of procuring prostitutes – some underage – for his friends and acquaintances. Trump’s Maga base has long clamoured for the release of classified documents about his case, believing they could incriminate establishment figures, in particular Bill Clinton (who has denied all knowledge of Epstein’s crimes).
Having been friends with Epstein for years before a bitter falling out in 2004, Trump took full advantage of the situation, repeatedly suggesting that there was explosive material possessed by authorities which would come to light if he was re-elected, and hinting Epstein might not have taken his own life.
Yet as Trump has backed away from his promises of disclosure on Epstein, Maga commentators have started to turn on him. The disgraced former general Mike Flynn, a sometime ally who has become a political commentator, posted on social media reminding the President – in capital letters – that the “EPSTEIN AFFAIR IS NOT GOING AWAY”.
Having stoked Epstein conspiracy theories for years, including indulging the idea he kept a so-called “client list” used to blackmail co-conspirators, Trump and his team may now find that their strategy comes back to bite them.
“[Threatening disclosure] was a typical Trump blow-hard kind of thing,” Wolff says. According to his reportage, Trump and Epstein were at one time even closer than had been previously thought.
Trump and Epstein, wealthy and connected men of similar ages, mixed in similar fields and socialised together frequently. They were on several occasions spotted at the same parties.
In 2002, Trump called Epstein a “terrific guy” in a New York Magazine profile, adding that “he likes beautiful women as much as I do, and many of them are on the younger side”. In audio files previously released on Wolff’s Fire and Fury podcast, Epstein said he had been Trump’s “best friend” for 10 years. Wolff has also said Trump’s nickname for Epstein was “Jeffy”.
“From 1988-89 through to 2004 Jeffrey Epstein and Donald Trump were the best friends,” Wolff, 71, says over the phone from his home in the Hamptons.
“These were Eighties guys, from a moment when having money forgave anything and everybody idolised anybody who had money. Having money gave you this extraordinary entitlement. This was the last blush of what it is to be a playboy. They had the money, the planes, the total disregard of middle class rules.
“They had the same interests. They did the same things, pursued the same activities, pursued very often the same women. Someone called me the other day and said ‘You don’t mean Trump was interested in little girls?’ I said ‘No … but they [Trump and Epstein] were both obsessed with models’.
“They started modelling agencies, invested in modelling agencies. Trump has his beauty pageants, Epstein had the Victoria’s Secret stuff [Epstein was an adviser to Les Wexner, the Victoria’s Secret boss].”
Wolff says the friendship centred on Palm Beach, Florida, where Epstein and Trump were neighbours. “Epstein had this set of a dozen Polaroids of Trump around Epstein’s swimming pool,” Wolff recalls. He alleges the images were held in Epstein’s safe, which the FBI seized when they raided his homes in New York and Palm Beach in July 2019.
“I remember three of them vividly. Two of the pictures had topless girls sitting in Trump’s lap, and one where Trump has a stain on the front of his [trousers] and three or five topless girls are pointing at it and laughing. These guys defined each other. Epstein is the best window through which to understand Trump.”
Last week, a report in It’salleged that Trump sent Epstein a card on his 50th birthday in 2003, with a drawing of a naked woman and inscribed “may every day be another wonderful secret”. Trump immediately denied doing so, claiming: “It’s not my language … it’s not my words.” He added he did not “draw pictures of women”.
“Voice Over: There must be more to life than having everything,” the note began.
Donald: Yes, there is, but I won’t tell you what it is.
Jeffrey: Nor will I, since I also know what it is.
Donald: We have certain things in common, Jeffrey.
Jeffrey: Yes, we do, come to think of it.
Donald: Enigmas never age, have you noticed that?
Jeffrey: As a matter of fact, it was clear to me the last time I saw you.
Trump: A pal is a wonderful thing. Happy Birthday — and may every day be another wonderful secret.
After the story, the White House has banned the WSJ from covering an upcoming trip to Scotland because of the “fake and defamatory conduct” and Trump has moved to sue the Rupert Murdoch-owned publication for $10 billion. The President has spoken of being subjected to a “witch hunt”.
On Monday, White House communications director Stephen Cheung said Trump once kicked Epstein out of his club for being a “creep” and called allegations about him “recycled, old fake news”.
After decades of friendship, in 2004, Trump and Epstein had what Wolff describes as an “acrimonious” falling out over a real estate deal, so were not close during Epstein’s alleged crimes at the so-called “Epstein Island”, Little St James in the US Virgin Islands. It was after that that criminal accusations first started to gather around Epstein, culminating in a 13-month prison sentence for prostitution in 2008.
In 2014, Epstein approached Wolff, a highly respected New York journalist who had been the media columnist of Vanity Fair, with a view to being written about. Wolff had just begun writing about Trump, work which would form the basis of Fire and Fury, the first of his accounts of the President’s time in the White House.
“Epstein said: ‘You can ask me anything, I have nothing to hide, and you judge for yourself whether I’m honest’,” Wolff recalls. After a couple of “pretty damn interesting” conversations, Wolff began attending the events Epstein held at his mansion on the Upper East Side, thought to be one of the largest private residences in New York.
“It was kind of extraordinary,” Wolff says. “The people there were amazing. From Bill Gates to Ehud Barak [former Israeli prime minister] to Larry Summers, just one person after another.”
Prince Andrew?
“Yeah,” Wolff says. “Epstein conducted these things at his dining table. People came in from morning until night. There were very few women, it had a men’s club feel to it. But it was kind of irresistible, frankly, and I confess to having a good time. The subjects were foreign policy, the economy. No girls, that was never a topic.
“Then in 2015, when Trump started to run [for the presidency], Epstein started to talk about his relationship with Trump, which was eye-opening. I was starting to write about Trump, so it was very valuable. In 2017, [Epstein] became friends with Steve Bannon and they bonded over their mutual obsession slash hatred of Trump. They talked about Trump all the time.”
As the authorities closed in on Epstein prior to his arrest in 2019, he remained in touch with Wolff. In a piece from 2020, The Last Days of Jeffrey Epstein, Wolff details the acrimony between Epstein and Trump. Epstein refers to Trump as a “moron”, and makes derogatory claims about his leadership style. “He lets someone else be in charge, until other people realise that someone else is in charge. When that happens, you’re no longer in charge.”
After the fall-out over their property deal, Wolff says Epstein came to believe it was Trump – who had close relations to the Florida law enforcement – who turned Epstein in before he was jailed for soliciting prostitutes in 2008.
In the same piece, Wolff quotes Bannon telling Epstein he was the “only person” he was afraid of during Trump’s first presidential campaign, implying he believed the financier knew dangerous secrets about Trump.
“As well you should have been,” Epstein is reported to have replied. It was during Trump’s presidency that Epstein was arrested.
Wolff’s own relationship with Epstein had a macabre denouement.
“The last message he wrote appears to be to me,” Wolff says. “He died on Saturday morning and I got the message on Friday evening. I had written a note through his lawyers asking how he was doing. The message was ‘pretty crazy. But still hanging around – no pun intended’. Then he died with the bedsheet around his neck a few hours later. It was very weird.”
The circumstances of Epstein’s death have become a lightning rod for conspiracy theorists. He was found in the early hours of August 10, 2019, hanging off the side of his cell’s bed. The official ruling was a suicide by hanging, but Epstein’s lawyers challenged that account. Two guards who were meant to check on him had fallen asleep, and two CCTV cameras in front of his cell malfunctioned at the critical moment. Surveys have suggested that only 15% of Americans believe Epstein died by suicide.
When the US Department of Justice finally released a tape of events that evening two weeks ago, analysts found that nearly three minutes had been cut out.
“It seems implausible that he could have killed himself in the way they say he would have had to have killed himself,” Wolff says, “but equally implausible that he would have been murdered and all of the people, the FBI agents and assistant US attorneys would either know something or keep quiet about it. I don’t know.”
In the years since Epstein’s death, Wolff has tried to draw attention to what he claims was the true extent of his relationship with Trump. But he has not gained much traction.
“I’ve been trying to place this stuff for a long time,” Wolff says, describing how he has pitched larger treatments of his “endless amounts of recordings” countless times, only for the plug to be pulled at the last minute.
“It’s so compelling that everyone’s always interested, but executives decide it’s too complicated and controversial. Because as soon as you start to deal with Epstein as a person with multiple dimensions, instead of just this evil guy, it freaks everybody out.”
He says he thinks partly the press has not been willing to further confront Trump’s friendship with Epstein.
“There has been, among the respectable press, a view that this subject is too icky,” Wolff says. “Good people don’t discuss this. He’s the President of the United States, how can you link him to the President of the United States without evidence … It has something to do with the fact that there is not the language in the post-MeToo world to discuss sex. You have to talk about sex, you have to make distinctions between girls and women, talk about the complicated idea of consent of victims. It’s very hard in the recent climate.
“People don’t know how to approach this,” he adds. “They think it’s going to be too hot to handle, the right wing is going to yell at us and the left wing is going to yell at us and the women are going to yell at us and Trump is going to yell at us. We’re not going to be a hero to anyone if we tell this story.”
To judge by the renewed interest in Wolff’s 100 hours of tapes this time, the weight of public pressure may prove decisive.