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Donald Trump and Jeffrey Epstein Had a 'Competition' to See Who Could 'Sleep With' Princess Diana First, Biographer Claims

Split photos of Donald Trump, Princess Diana and Jeffrey Epstein.
Source: MEGA

Donald Trump and Jeffrey Epstein reportedly were both eager to sleep with Princess Diana.

Aug. 15 2025, Published 9:10 a.m. ET

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Donald Trump and Jeffrey Epstein were allegedly on a competitive mission to sleep with Princess Diana following her 1996 divorce from King Charles.

According to biographer Michael Wolff — who Trump's team despises and has long branded a "liar" — the President of the United States and his former friend-turned-pedophile were eager to get in bed with the late British royal before she tragically died in a car crash at age 36 in 1997.

"They had a competition, Trump and Epstein," Wolff claimed during Daily Beast's "Inside Trump’s Head" podcast. "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."

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Donald Trump Saw Princess Diana as 'the Ultimate Trophy Wife'

Image of Donald Trump allegedly sent Princess Diana flowers after her divorce from King Charles.
Source: MEGA

Donald Trump allegedly sent Princess Diana flowers after her divorce from King Charles.

This isn't the first time Trump has been accused of pursuing the princess either.

In 2015, former British TV anchor Selina Scott wrote in a column for the U.K. paper The Sunday Times that Trump saw Diana as "the ultimate trophy wife" and tried to win her over after she divorced Charles in 1996 by allegedly sending her a large arrangement of flower bouquets to Kensington Palace.

Diana reportedly sent a polite thank-you letter for the flowers, however, Scott claimed the princess confided in her privately to admit that Trump "gives me the creeps."

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Donald Trump Thinks He 'Could Have' Slept With Princess Diana

Image of Donald Trump was confident he 'could have' slept with Princess Diana if she didn't tragically die in 1997.
Source: MEGA

Donald Trump was confident he 'could have' slept with Princess Diana if she didn't tragically die in 1997.

Trump himself has openly admitted to wanting to sleep with the beloved princess.

During a 1997 interview with Howard Stern — which aired just months after Diana's devastating death — Trump confidently claimed he "could have" succeeded in hooking up with the royal highness if he had the chance.

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Image of Donald Trump claimed he could have 'nailed' Princess Diana if given the chance.
Source: MEGA

Donald Trump claimed he could have 'nailed' Princess Diana if given the chance.

"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?" The Howard Stern Show host asked the businessman-turned-politician.

"I think I could have," Trump declared.

The following year, Trump returned to Stern's radio show and doubled down on his claims, as he said Diana was "crazy, but these are minor details," before admitting he would have slept with the princess "without hesitation" if the opportunity had come before she died.

Donald Trump Met Wife Melania in 1998

Image of Melania and Donald Trump met in 1998 and married in 2005.
Source: MEGA

Melania and Donald Trump met in 1998 and married in 2005.

Shortly after Diana's death, however, Trump was introduced to his current wife, Melania Trump.

While Hunter Biden recently claimed Melania was "introduced" to Donald by Jeffrey, the president's team denied the claim and threatened to sue the former first son for $1 billion if he did not "immediately issue a full and fair retraction of the video" and "immediately issue an apology for the false, defamatory, disparaging, misleading, and inflammatory statements."

In Melania's self-titled 2024 memoir, the first lady said she met her husband at a September 1998 Fashion Week party at the Kit Kat Klub in New York City, where she was immediately "drawn to his magnetic energy."

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