Donald Trump-Jeffrey Epstein Allegations by Michael Wolff: Five Takeaways

Author and journalist Michael Wolff has made a new series of claims surrounding the relationship between former President Donald Trump and Jeffrey Epstein, including what he described as their competitive playboy lifestyles, allegations about a real estate deal in Florida, and a claim that embarrassing photographs of Trump were found in Epstein’s safe.
Wolff, who has written a number of books about Trump, discussed the friendship between the Republican candidate and the late convicted sex offender on his Fire and Fury podcast. The episode was released on Thursday, just five days before the election.
Below, Newsweek has compiled five key moments from Wolff’s podcast. Newsweek has not independently verified these claims and has contacted Trump’s team for comment via email on Friday outside of business hours. This article will be updated if a response is received.
Wolff did not speculate that Trump was involved in the sex trafficking, and other crimes, committed by the billionaire financier for years, but he did say that the former president would have been aware of “girls” being at Epstein’s home.
Wolff said that Epstein was his “secret source” when he wrote his trilogy of books about Trump’s time in the Oval Office. Wolff’s books on Trump have been questioned over their accuracy previously and were dismissed by White House press secretary under Trump from 2017 to 2019, Sarah Huckabee Sanders, who said at the time that Fire and Fury contained “mistake after mistake after mistake.” She questioned Wolff’s integrity, saying, “I think you have to look at this author’s track record,” before referring to the book as “tabloid gossip” and “full of lies.” Wolff has said his reporting is backed up by “dozens of hours” of audio recordings of senior staff.
Wolff said these new claims stem from nearly 100 hours of interviews he conducted with Epstein before the latter died by suicide in August 2019 while awaiting trial on sex trafficking charges.
Epstein’s death in 2019 left numerous unanswered questions regarding his associations with powerful figures, including Trump. Though his death was ruled a suicide, a portion of the public has remained skeptical about what actually happened and even Epstein’s lawyers have challenged that ruling.
Wolff makes frequent references to how and why Trump and Epstein became close friends in the 1980s.
“I think they saw themselves as embodying this moment, which was money, women, and status,” Wolff said. “We now see Epstein as the sexual monster. But certainly, at least in Epstein’s telling, he and Trump were, in this regard, brothers in arms.”
Wolff added that Epstein believed that he could hang around with the “vulgarian” Trump to make his actions appear more reasonable in comparison.
“I certainly never got an indication that Epstein was questioning himself. But in fact, he seemed to regard Trump’s behavior as somehow proving that his own was far more reasonable… he said that Trump has no scruples,” Wolff said.
Wolff said that Trump and Epstein were essentially in competition over who could maintain the biggest playboy lifestyle, including sleeping with the most women.
“This was the 1980s; models were the sexual currency of the time,” Wolff said.
The author also says that Trump and Epstein had a competition over who would be the first to sleep with the late Princess Diana of Wales.
“There was one point in which they had a competition about who would be the first one to sleep with Princess Diana. Now, I don’t think that ever happened,” Wolff said. “These guys were playing at the highest stakes they could play.
“There was constant betting about who could get what girl first, and then the status thing was all about what money could buy and what it could buy in that golden-crusted Trump real estate sense,” Wolff added.
Wolff also detailed how Trump and Epstein fell out over a real estate deal in 2004.
According to Wolff, Epstein had placed a bid on a house in Palm Beach, Florida, for around $36 million and asked Trump for advice about moving the property’s swimming pool. The former president is then said to have “gone around Epstein’s back” and bid $40 million for the house, said Wolff.
“Epstein knew that Trump didn’t have the money, therefore Epstein’s conclusion was that he must be fronting for someone,” Wolff said.
“And in fact, in that classic money laundering setup, Trump bought the house for $40 million, bought it through borrowed money, and then the house was put on the market not long afterward and immediately sold for $96 million to one of the oligarchs in the close [Russian President Vladimir] Putin circle.”
Epstein pleaded guilty to soliciting prostitution from a minor in 2008, just a few years after he and Trump fell out. Wolff said that Epstein believed his legal issues arose “because it was Trump who first dropped a dime on him.”
“And Trump would have known about the girls, because he was in and out of Epstein’s house,” Wolff said.
In 2019, Trump said he had a “falling out” with Epstein. “I haven’t spoken to him in 15 years. I was not a fan of his, that I can tell you.”
Wolff said that while interviewing Epstein, the financier would occasionally bring out dozens of photos of Trump from the late 1990s. Some of the photos featured Trump in Epstein’s Palm Beach house surrounded by young women, added Wolff.
“And the young girls are topless, and in some of the pictures, they’re sitting on his lap. And then there’s one I especially remember where there’s a telltale stain on the front of Trump’s pants, and the girls are pointing at him and laughing,” Wolff said.
Wolff added he would retrieve these photos from a safe at his home.
“And I would say it was likely that they would have been there when the FBI, Trump’s FBI at that point, not to put too fine a point on it, raided Epstein’s house and took the contents of the safe in 2019,” Wolff said.
Wolff said that the two even shared a girlfriend.
“I think that Trump was envious of Epstein’s girlfriends, which included actresses and models,” Wolff said.
This includes Stacey Williams, said Wolff, the former model who alleges Trump groped her in 1993 after Epstein introduced them. Williams said the incident was part of a “twisted game” between Trump and Epstein, The Guardian reported in October.
Trump’s national press secretary for his 2024 campaign, Karoline Leavitt, told the British paper: “These accusations, made by a former activist for Barack Obama and announced on a Harris campaign call two weeks before the election, are unequivocally false. It’s obvious this fake story was contrived by the Harris campaign.”
“This was always part of the admiration that Trump had for Epstein. And in fact, there was a moment in which they actually shared a girlfriend,” Wolff said. “They were both openly, possibly proudly, going out with the same girl at the same time.”
Wolff did not reveal the name of the woman who dated Trump and Epstein at the same time.
“In that moment in time, there was a particular kind of sexual excess and license and rich guy, masculine cruelty that was not just allowed, but celebrated,” Wolff said.