ROYAL RACE

Trump and Epstein’s Twisted Race to Sleep With Princess Diana: Author

The president tried to woo Princess Diana. She reportedly said that he gave her the “creeps.”

Jeffrey Epstein and President Donald Trump once competed to sleep with Princess Diana to further their own celebrity status, says the president’s longtime biographer, Michael Wolff.

Wolff made the revelation on the Daily Beast’s Inside Trump’s Head podcast, telling host Joanna Coles that both Epstein and Trump attempted to woo the British princess and, in the process, reach the apex of the world’s most prominent social networks.

“They had a competition, Trump and Epstein,” Wolff said. “Of who would be the one, the first one to sleep with Princess Diana? ... They just understood, what could you get from these people? Both Trump and Epstein. What can you get from somebody, is the question you would always ask about anybody.”

Wolff said that the two New York-born businessmen each sought to further their fame and fortune. Diana could do just that.

The former British TV anchor Selina Scott wrote in 2015 that Trump saw Diana as “the ultimate trophy wife,” adding that he tried to impress her after she divorced then-Prince Charles in 1996. He reportedly sent her huge bouquets at Kensington Palace.

The always-polite Diana responded with a thank-you letter for the flowers. However, she reportedly told Scott in private that Trump “gives me the creeps.”

Trump has spoken publicly about his desire to sleep with Diana in the past. He said in a 1997 interview on The Howard Stern Show that he “could have” had sex with the British royal.

Stern asked Trump, “Why do people think it’s egotistical of you to say you could’ve gotten with Lady Di? You could’ve gotten her, right? You could’ve nailed her?”

“I think I could have,” Trump replied.

Trump made a similar declaration in a separate 2000 broadcast with Stern, adding that Diana was “crazy, but these are minor details.” He said that he would have slept with the princess, who died in 1997, “without hesitation” if given the chance.

Wolff first spoke of Epstein and Trump’s alleged competition to sleep with Diana on his podcast just before the 2024 presidential election. Trump’s camp denied the claim at the time, and released a second statement to the Daily Beast on Aug. 14, 2025.

“Michael Wolff is a lying sack of s--t and has been proven to be a fraud,” said White House Communications Director Steven Cheung. “He routinely fabricates stories originating from his sick and warped imagination, only possible because he has a severe and debilitating case of Trump Derangement Syndrome that has rotted his peanut-sized brain.”

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Trump continues to face pressure for his past friendship with Epstein. He has tried to distance himself from the pedophile and has begged the public to move on from the issue.

The growing rumor among critics of Trump is that the president is named in the so-called “Epstein files” that are yet to see the light of day—something Trump’s old pal, Elon Musk, alleged during their high-profile breakup on June 5, 2025.

While details about the extent of Trump and the convicted sex offender’s relationship remain murky, Wolff, who has interviewed Epstein, said on Thursday’s show that “Epstein and Trump functioned as a duo.” He also alleged that Andrew, Epstein, and Trump were at one point like “three musketeers.”

“They were, you know, grifter buddies, basically,” he said. “I mean, they had the same interests—interests in women–and also in money. How do you get money? How do you, these two guys, who don’t work for major corporations, [who] don’t have relationships with major banks, or don’t have good relationships?”

The answer, he later said, was by their endless pursuit of climbing up the social ladder.

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