Donald Trump and Jeffrey Epstein Bet on Who Would Sleep With Princess Diana First, Claims Author

Author and popular journalist Michael Wolff has stirred fresh controversy with new claims about the connection between former President Donald Trump and the late billionaire Jeffrey Epstein. In episode 22 of his Fire and Fury podcast, released Thursday, Wolff revealed a scandalous friendship between the two. According to Wolff, Trump and Epstein allegedly made a bet over who could sleep with Princess Diana first. Moreover, the two reportedly engaged in a competition to see who could sleep with the most women.

As reported by Newsweek, Wolff said, "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." He referred to Trump and Epstein as 'two playboys' before sharing the claim about Diana. Wolff added, "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. Now, I don't think that ever happened." At that time, Diana was the most famous woman in the world, as reported by the Daily Mail.

The author also said, "Partly because sex seemed to be their singular focus, I believe they thought they could sleep with any woman they wanted to, including a princess." Back then, Diana was still married to the now-King Charles III. Furthermore, Wolff claimed that the bet took place when Trump and Epstein were in the same social circles. Trump's fascination with Diana is also not a secret. In a 1997 interview with Howard Stern, following Diana's tragic death, the former President openly said he believed he could have had a romantic relationship with her.

Wolff has not stayed away from controversies, with many critics constantly questioning the reliability of his claims about Trump. Among his critics is former press secretary Sarah Huckabee Sanders, who served under Trump from 2017 to 2019. Sanders once spoke out about Fire and Fury, claiming it had 'mistake after mistake after mistake.' She further accused Wolff of being more of a tabloid writer whose work was full of lies. Despite the criticism, the author has repeatedly defended his work, insisting that he can support every claim he makes in the book. 

On the other hand, Epstein’s death has left many questions unanswered, especially about his connection with powerful figures like Trump, whom he got to know back in the 1980s. However, as allegations of sexual misconduct began to swirl around Epstein, Trump’s camp claimed that the former president distanced himself from Epstein much before these heinous acts took place.

According to Wolff, jealousy may have also played a role in their eventual rift; apparently, Trump allegedly admired Epstein's connections with several women, including model Stacey Williams, who claimed that Trump had groped her in 1993. As per later reports, Epstein thought Trump had turned him in, which resulted in his conviction for soliciting a minor in 2008. Trump’s team has strongly denied all of Wolff’s assertions, pushing back against any suggestion of jealousy or involvement in Epstein’s legal troubles.