Author and journalist Michael Wolff made a startling claim in a recent podcast episode, alleging that Jeffrey Epstein and Donald Trump once “placed bets on who could sleep with Princess Diana.” Wolff, known for his books on Trump’s life, suggested that both men were caught up in a rivalry focused on women and status.
The time frame referenced appears to be when Diana was still married to Prince Charles, now King Charles III, and one of the world’s most famous figures. According to Wolff, Diana represented a rare “get” for both Epstein and Trump, making her an attractive target for their supposed competition.
“Diana and the royal family symbolized the ultimate prize for these two men,” Wolff said. He claimed both men were intensely driven by the belief they could seduce any woman, including a member of royalty. This alleged competition highlighted what Wolff described as a “sex-obsessed” mindset shared by both Epstein and Trump during that era.
Wolff also revealed an audio recording from a 2017 interview with Epstein, where Epstein allegedly discussed Trump’s leadership style in the White House. “His people fight each other,” Epstein reportedly said in the recording. He added that Trump would “poison the well” for his rivals on the outside. Wolff claimed the interview took place in a New York restaurant, further indicating the two men’s complex relationship. Trump’s team, however, has stated that Trump distanced himself from Epstein years ago. But Wolff painted a different picture, describing the two as close associates in their early years, sharing an interest in wealth, status, and women.
Wolff’s comments went beyond the claim about Princess Diana. He delved into Epstein and Trump’s friendship, which he alleges started in the 1980s. According to Wolff, their relationship involved frequent competition. Epstein is said to have once remarked that Trump had “no scruples,” highlighting what Wolff described as a “brothers in arms” attitude toward the pursuit of power and influence. “We now recognize Epstein as a predator,” Wolff said, “but at the time, they saw themselves as sharing similar values—wealth, women, and social dominance.”
Trump, however, publicly distanced himself from Epstein after sexual abuse allegations emerged against the financier. In 2019, Trump said he hadn’t spoken to Epstein in 15 years and insisted, “I’m not a fan.”
Trump’s team responded forcefully to Wolff’s claims, accusing the author of attempting to sway public opinion ahead of the upcoming election. Trump campaign communications director Steven Cheung dismissed Wolff as a “disgraced writer” who has no ethics. “Michael Wolff’s allegations are pure fiction,” Cheung stated. He went further to accuse Wolff of timing his comments to interfere with the election, suggesting Wolff’s claims were intended to support Kamala Harris.
Cheung added, “Wolff is a failed journalist who resorts to lies for attention.” The Trump campaign maintained that these allegations are a distraction and part of a longstanding attempt by Wolff to undermine Trump’s public image.
