Michael Wolff, Trump’s longtime biographer, claimed that Trump and Jeffrey Epstein once competed for Princess Diana’s attention. He said both men saw her as a path to greater celebrity and influence.
Speaking on the Daily Beast’s “Inside Trump’s Head” podcast, Wolff told host Joanna Coles that Epstein and Trump each tried to woo Diana, hoping to gain status in elite social circles.
“They had a competition, Trump and Epstein,” Wolff explained. “The question was, who would be the first to sleep with Princess Diana? For them, relationships were always about what you could gain.”
Wolff explained that both New York businessmen were eager to increase their fame and wealth. They believed that a connection with Diana could provide exactly that kind of power.
In 2015, broadcaster Selina Scott recalled Trump’s pursuit of Diana. She said he viewed her as “the ultimate trophy wife” and sent large bouquets to Kensington Palace soon after her divorce from Prince Charles.
Diana politely thanked Trump for the flowers in a short note. Yet broadcaster Selina Scott later said the princess admitted privately that Trump “gave me the creeps.”
Trump also spoke openly about his interest in Diana. In a 1997 interview on Howard Stern’s radio show, he said he “could have” slept with the British princess if he wanted.
During the exchange, Stern pressed Trump further. He asked, “Why do people think it’s egotistical of you to say you could’ve gotten with Lady Di? You could’ve nailed her, right?”
“I think I could have,” Trump replied at the time. His comments drew attention because Diana remained one of the most admired public figures in the world.
In a separate 2000 interview with Stern, Trump repeated the claim. He said Diana was “crazy” but added that these were “minor details” that would not have stopped him.
Trump then said he would have slept with the princess “without hesitation” if given the chance. Diana, however, died tragically in a Paris car crash in 1997.
Wolff first raised the claim about Trump and Epstein competing for Diana before the 2024 election. At that time, Trump’s team dismissed the story and issued a strong denial.
White House Communications Director Steven Cheung attacked Wolff directly. “Michael Wolff is a lying sack of s–t and has been proven to be a fraud,” Cheung said in a statement to the Daily Beast.
Cheung added that Wolff often fabricates stories from his imagination. He accused the author of having what he called “Trump Derangement Syndrome” and claimed his reporting lacked any credibility.
Even with denials, Trump continues to face questions about his past friendship with Epstein. Trump insists he ended their connection long ago and often urges the public to move forward.
Still, rumors remain. Critics argue that Trump could be named in the so-called “Epstein files,” which have not yet been released. In June, Elon Musk repeated that claim after his split with Trump.
Details of Trump’s past relationship with Epstein remain unclear. On the podcast, Michael Wolff said he had interviewed Epstein and claimed, “Epstein and Trump functioned as a duo.”
Wolff also alleged that Trump, Epstein, and Prince Andrew sometimes acted like “three musketeers.” He described them as close companions driven by similar goals and interests, rather than genuine loyalty.
“They were grifter buddies,” Wolff said. “They shared the same interests, especially in women and in money. How do you get more of both? That was their main question.”
According to Wolff, their solution was constant social climbing. He claimed they pursued fame and wealth not through steady work, but by attaching themselves to high-profile circles and powerful people.
