Ghislaine Maxwell Claimed Jeffrey Epstein May Have Been 'Set Up' on a Date With Princess Diana

The convicted sex offender alleged that the late Princess met Epstein through one of her closest friends at a high-society event — while a Trump biographer has made the explosive claim that the disgraced financier was given a chilling "job" to manoeuvre his way to Diana's side.

Ghislaine Maxwell — the convicted sex offender currently serving a 20-year prison sentence for her role in Jeffrey Epstein's abuse network — made a series of extraordinary and deeply unsettling claims about the late Princess Diana, alleging that the beloved royal may have been romantically set up with the disgraced financier.

Speaking to Deputy Attorney General Todd Blanche, among other officials, during a July 2025 interview with the US Justice Department, the former socialite and Jeffrey's long-time co-conspirator claimed that Diana and Jeffrey may have crossed paths under circumstances that were anything but accidental.

'I Don't Know If She Was Being Set Up as a Date for Him'

Ghislaine, delving into the murky details of her years-long relationship with Jeffrey — who was convicted of sex trafficking in 2008 before his death in prison in 2019 — told investigators that the financier had spent a considerable period living in London prior to the pair meeting.

It was there, she claimed, that Jeffrey began cultivating ties with some of Britain's most rarefied social circles, including a friendship with Rosa Monckton, one of Princess Diana's most intimate confidantes.

Ghislaine alleged that it was through this connection that Jeffrey encountered the then-Princess of Wales at what she described as a "big event" — large enough to have made the news — which she believed Monckton had organised.

"I don't know if he sat with Diana or he met with Diana and he'd already met her. I don't know, but this event, I believe was organised by Rosa," Ghislaine said, adding that photographs of the occasion were believed to exist.

Yet it was her next remark that will send shockwaves through those who cherish Diana's memory.

"I don't know if she was being set up as a date for him, maybe because she — I don't want to speak bad of Diana but… I'm not going to do that," Ghislaine said, stopping herself short — leaving a question hanging in the air that she appeared unwilling, or unable, to answer.

'Who Would Be the First to Sleep With Princess Diana?': The Sickening Competition Between Epstein and Trump

Ghislaine's claims did not emerge in isolation. They were given a deeply troubling new dimension by Trump biographer Michael Wolff, who made his own staggering allegations during an August 2025 episode of his podcast "Inside Trump's Head", co-hosted with Joanna Coles.

Michael claimed that both Jeffrey and Donald Trump had cynically exploited their friendship with then-Prince Andrew Mountbatten-Windsor as a means of clawing their way into the upper echelons of British high society. But their ambitions, he alleged, extended far beyond mere social climbing.

"There was a point in which they had a competition, Trump and Epstein: Who would be the one, the first one, to sleep with Princess Diana?" Michael said — words that will strike many as nothing short of grotesque.

More disturbing still was Michael's account of the unofficial "position" that Jeffrey is alleged to have assumed at social functions attended by the Princess.

Through his relationship with Andrew, Michael claimed, Jeffrey had taken it upon himself to ensure that there was never an empty seat beside Diana at any event she graced with her presence.

"Epstein had the job of when whoever was sitting — formally sitting — next to Diana got up to go to the bathroom or whatever, then Epstein would be the guy who would then warm the chair," Michael explained — painting a chilling portrait of premeditated predation aimed at one of the most famous and vulnerable women in the world.

Trump's 'One Regret': The Man Who Boasted He Could Have 'Nailed' the Princess

Donald, for his part, has never been shy about his fixation with Princess Diana. In his 1997 book "Trump: The Art of the Comeback", he wrote with characteristic shamelessness that his sole romantic regret was never having had the chance to pursue her.

"I only have one regret in the women department — that I never had the opportunity to court Lady Diana Spencer. I met her on a number of occasions," he wrote.

Yet the carefully crafted veneer of wistful admiration told only part of the story. As revealed in an excerpt from Christopher Andersen's biography "The King", seen by Newsweek, the US president had in fact aggressively pursued Diana following her divorce from King Charles III — advances that were firmly and repeatedly rebuffed.

Rather than accepting rejection with any semblance of grace, he later boasted on radio that he could have "nailed her if I wanted to" — but only, he crudely added, if she had first passed an HIV test.

It is a remark as revealing as it is revolting — and one that, in light of these latest allegations, casts the president's long-professed "admiration" for the Princess in a sordid and deeply sinister new light.