Trump’s Alleged Princess Diana ‘Bet’ With Epstein Sparks Global Outrage and Royal Backlash

In a scandal that has sent shockwaves across both political and royal circles, explosive new revelations have surfaced about Donald Trump’s alleged fixation on Princess Diana—claims that now intertwine with his decades-long association with convicted sex offender Jeffrey Epstein.

The bombshell was dropped by journalist Michael Wolff, Trump’s former biographer and a writer who was once in line to document Epstein’s life. According to Wolff, Trump and Epstein formed what they called a “committee,” an unholy alliance in which they reportedly wagered on which of them could have sex with Princess Diana first after her divorce from now King Charles.

This revelation, already appalling on its own, gains further depth following audio clips of Trump on The Howard Stern Show. In one segment, Trump crudely remarked that before sleeping with Diana he would insist she take an HIV test—a comment many observers have described as degrading and disturbing. Palace insiders and close friends of Diana have since confirmed she found Trump’s advances “creepy” and “persistent to the point of harassment.” British presenter Selina Scott even revealed that Diana once confided Trump seemed to be stalking her, sending her an unsettling cascade of roses and orchids despite her clear lack of interest.

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In fact, evidence suggests Diana actively avoided events where Trump might appear. Friends say she felt cornered and bewildered by the relentless pursuit. This campaign of unwanted attention did not end after her tragic death in 1997—Trump continued to make lewd, suggestive remarks about her publicly in the years that followed, further fueling accusations of objectification and disrespect.

The British royal family has reportedly reacted with “white-hot rage” to the latest revelations. Sources say King Charles is now personally ensuring Trump will have no future engagements involving the Crown. Diana’s younger brother, Charles Spencer, has vowed to push back, allegedly gathering letters and testimonies from her inner circle to expose Trump’s behavior. Even Princes William and Harry—who have not always been aligned publicly—are said to be united in their disgust.

These revelations come as Trump faces increasing scrutiny over his connection to Epstein, whose client lists and court files remain the subject of legal battles. Multiple reports—including CNN coverage—state that Trump was informed his name appeared in Epstein-related documents. Although the Justice Department later claimed the reference was “not credible,” critics and former allies alike question why the former president is so eager to keep the majority of Epstein’s files sealed.

The Trump-Epstein connection stretches back decades, rooted in their shared social orbit of elite parties, beauty pageants, and modeling agencies—settings that have raised serious questions about the exploitation of young women. Epstein allegedly even claimed he and Trump would “share girlfriends” and compete over sexual conquests. One accuser, former model Stacy Williams, has publicly claimed Trump groped her in Epstein’s presence in the 1990s—an allegation Trump denies.

Political analysts say this scandal is different from Trump’s prior controversies. While many allegations in the past have been brushed aside by his loyal base, the intersection of Epstein’s sex trafficking crimes, Princess Diana’s enduring cultural legacy, and the royals’ fierce defense of her memory could shift public opinion decisively. Even some of Trump’s long-time supporters and conservative media figures are reportedly expressing unease privately.

Critics argue the pattern is now undeniable: a history of degrading comments about women—from the infamous Access Hollywood tape to public remarks about his own daughter—paired with repeated associations with men like Epstein.

For many, the Diana revelations are the tipping point. “This isn’t about politics anymore,” one commentator wrote, “it’s about basic human decency.”

If more documentary evidence surfaces—particularly from Diana’s own inner circle—it could mark a political and reputational reckoning for Trump unlike anything he’s faced before.

The world is now watching closely, and according to those close to the investigation, this is only the beginning.