A recent report from journalist Michael Wolff, who once considered writing Jeffrey Epstein’s biography, alleges a disturbing “committee” between Donald Trump and Epstein in New York in the 1990s — a bet over who could sleep with Princess Diana first after her divorce from now-King Charles. On Howard Stern’s radio show, Trump later claimed he “could have definitely” had sex with Diana and would have insisted she take an HIV test.
Friends of the late princess, including British presenter Selina Scott, recalled Diana confiding that Trump’s persistent gifts of roses and orchids felt “creepy” and bordered on stalking. In his 1997 book The Art of the Comeback, Trump wrote that his only regret “in the woman department” was never courting Diana, describing her as a “dream lady.” That same year, he inscribed a copy to Epstein: “To Jeff, you are the greatest.”
Years later, Trump told Breitbart that Diana “kissed his ass,” prompting her brother, Charles Spencer, to publicly fire back, saying she considered Trump “worse than an anal fissure.” The resurfaced allegations have reignited criticism of Trump’s conduct toward the late princess and his close association with Epstein.
In a later interview, Donald Trump denied pursuing Princess Diana, claiming he met her only once in a handshake line and dismissing reports of his predatory behavior as “totally false.” This account contradicts previous claims from Diana’s friends that his behavior felt like stalking. Trump’s late ex-wife Ivana criticized Diana in the 1990s for “whining” about her marriage, saying she should “give me a break” and move on.
A MeidasTouch segment also revisited Trump’s infamous Access Hollywood deposition, where he reiterated his belief that “stars” can “do anything” to women, including grabbing them without consent, calling it “historically” true. The host connected this pattern to Trump’s alleged creepiness toward Diana and other members of the royal family, noting his odd public comments — including enthusiasm over a satirical suggestion that the U.S. join the British Commonwealth.
