Former President Donald Trump and the late disgraced financier Jeffrey Epstein once made a bet over who could seduce the late Princess Diana first, author and journalist Michael Wolff has said on a podcast.
Wolff, the veteran reporter best known recently for his trilogy of books on the Trump White House—Fire and Fury, Siege: Trump under Fire and Landslide—said that he had a “secret source” when writing the first book and it was “Trump’s old friend Jeffrey Epstein.”
His latest explosive claims, which Newsweek has not independently verified, were made in episode 22 of his podcast Fire and Fury released on Thursday, five days before the culmination of a closely contested election between Trump and Vice President Kamala Harris.
Newsweek reached out to Trump’s office for comment on Friday outside business hours. This article will be updated if a response is received.
In the podcast, hosted by Wolff and former Condé Nast editor James Truman, Wolff details what he says was a close relationship between Trump and Epstein, the convicted sex offender who died in 2019 in jail while awaiting trial on sex trafficking charges.
“I probably have one hundred hours of Epstein talking about the inner workings of the Trump White House and about his long-standing, deep relationship with Donald Trump,” Wolff said on the podcast.
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He described Trump and Epstein as “two playboys very much styling themselves as playboys in that [Hugh]t Hefner sense who palled around for the better part of 15 years,” before making the claim about the late princess.
“I mean, there was one point in which they had a competition about who would be the first one who would sleep with Princess Diana.” He added: ” Now, I don’t think that ever happened.”
Some critics have questioned the accuracy of some of Wolff’s previous claims about Trump and the Trump administration. Sarah Huckabee Sanders, White House press secretary under Trump from 2017 to 2019, 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 responded that he has recordings and notes and stands by “absolutely everything in the book.”
In the latest podcast, Wolff claims that there was a sense of competition between Trump and Epstein, especially when it came to women, and that at one point Epstein was “brought in to be a Princess Diana walker, in other words, when he would be seated next to her when the seat became empty…
“I mean, these guys were playing at the highest stakes they could play. I mean, there was constant kind of betting about who could get what girl first.”
Wolff said that the alleged bet occurred at a time when Trump and Epstein socialized together in the same circles. “They were very competitive about the women,” he said.
He alluded to former model Stacey Williams previously recalling there was a competition between them.
“There was a moment in which they actually they shared a girlfriend, ” Wolff said. “They were both openly, possibly proudly going out with the same girl at the same time… let me just make the point that in a moment in time there was a particular kind of sexual excess and license and cruelty, masculine cruelty, rich guy masculine cruelty that was not just allowed but celebrated.
“Yeah, they think that Epstein and Trump really were two of its exaggerated exponents. Of course, we see now Epstein as the sexual monster, but certainly, you know, at least in Epstein’s telling, he and Trump were pretty much in this regard brothers in arms.”
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.
Trump’s admiration for Diana, who died in a car accident in 1997, has been well documented. He told Howard Stern in a 1997 interview after her death that he thought he “could have” had a relationship with her.
In a later interview with Stern, in 2000, Stern asked Trump: “You would have slept with her?”
“Without even hesitation,” Trump replied. “I tell you what, I think she’s magnificent. Lady Di was truly a woman with great beauty. I’ve seen her a couple of times…She was really beautiful and people didn’t realize that beautiful. She was supermodel beautiful. She had the height, she had the beauty, she had the skin, the whole thing.”