On August 15, 2025, a bombshell revelation surfaced implicating President Donald Trump and the late Jeffrey Epstein in a disturbing competition to pursue Princess Diana, intensifying scrutiny of their decades-long relationship.
The claim, reported by Raw Story, stems from Trump biographer Michael Wolff, who alleged on The Daily Beast’s podcast “Inside Trump’s Head” that Trump and Epstein vied to be the first to sleep with the Princess of Wales before her tragic death in a 1997 Paris car crash.
The White House fiercely denied the allegations, but the report has reignited controversy over Trump’s ties to Epstein, the disgraced financier who died in 2019 while awaiting trial on sex-trafficking charges, amid ongoing demands for transparency regarding Epstein’s files.
Michael Wolff, who interviewed Epstein extensively in 2017 and claims to possess over 100 hours of recorded conversations, told The Daily Beast that Trump and Epstein engaged in a “competition” over Princess Diana, viewing her as a potential conquest.
“They had a competition, Trump and Epstein,” Wolff said, adding that both men asked, “What can you get from somebody?” in reference to their pursuit of influential figures like Diana, per Raw Story.
The claim aligns with Trump’s documented comments about Diana, including a 2015 report by journalist Selina Scott that Trump sent Diana flowers after her 1996 divorce, hoping she would become his “trophy wife,” and his 1997 and 2000 statements to Howard Stern claiming he “could have” slept with her “without hesitation.”
The White House, through Communications Director Steven Cheung, issued a vehement denial, calling Wolff a “lying sack of s–t” with a “peanut-sized brain” suffering from “Trump derangement syndrome.”
Cheung labeled the allegations “fabricated” and dismissed Wolff’s credibility.
The fierce response reflects the administration’s broader efforts to distance Trump from Epstein, including prohibiting aides from discussing the matter without high-level approval, as reported by NBC News on July 24, 2025.
Context of Trump’s Epstein Connection
Trump’s relationship with Epstein, spanning the 1990s and early 2000s, has drawn renewed attention following a July 2025 Wall Street Journal report revealing a “bawdy” letter Trump sent Epstein for his 50th birthday, including a crudely drawn picture of a naked woman, which Trump denied authoring despite evidence of his past drawings.
Epstein claimed in 2017 to have been Trump’s “closest friend for ten years,” and flight logs confirm Trump flew on Epstein’s private jet at least seven times in the 1990s, per multiple media outlets.
A 1992 NBC video showed them socializing at Mar-a-Lago, and a 2002 New York Magazine quote had Trump praising Epstein as a “terrific guy” who liked women “on the younger side,” per The Independent.
Further complicating matters, a July 29, 2025, Slate article by Jack O’Donnell, former president of Trump Plaza Hotel and Casino, recounted an incident in the early 1990s where Trump and Epstein brought three young girls, including 19-year-old tennis star Gabriela Sabatini, onto the casino floor, violating age restrictions.
Trump allegedly made crude comments about Sabatini’s body and said, “Jeffrey likes them young – too young for me.”
The White House has denied related claims, including a 2019 allegation by Epstein accuser Maria Farmer that Trump visited Epstein’s Manhattan office in 1995.
MAGA Backlash and Victim Outcry
The Epstein saga has sparked fury among Trump’s MAGA base, who expected him to release Epstein’s files as promised during his 2024 campaign.
A July 2025 Justice Department memo, concluding Epstein died by suicide and maintained no client list, drew outrage, with Steve Bannon’s War Room podcast guest Blue Jackson declaring, “Trump has become the deep state,” on July 11, 2025.
House Republicans, including Rep. Tim Burchett, have pushed for the Epstein Files Transparency Act, while Speaker Mike Johnson considers a vote to unseal documents.
Epstein’s victims have also voiced dismay.
Jennifer Araoz’s attorney, Eric Lerner, challenged Trump on CNN on August 2, 2025, to meet survivors, arguing against a potential pardon for Epstein’s associate Ghislaine Maxwell, who was moved to a minimum-security prison in Texas.
Annie Farmer told ABC News on July 26, 2025, that a Maxwell pardon would be “devastating,” and Teresa Helm warned MSNBC of a “crumbling justice system.”
Posts on X, like @mmpadellan’s on August 4, 2025, alleged Trump used “thousands of agents” to scrub files protecting his identity, though such claims remain unverified.
The Diana allegations, combined with a Wired investigation revealing that “full raw” Epstein prison footage was edited, per VICE, have deepened public distrust.
The FBI’s ongoing search for Epstein files, as confirmed by Judicial Watch’s lawsuit, contradicts DOJ claims of a closed investigation.
With Trump’s approval rating at 39% per an ABC News/Washington Post/Ipsos poll, the controversy risks further eroding his support as bipartisan calls for transparency grow, per TIME.
The administration’s defensive posture, including rejecting proposals to address the uproar, signals ongoing challenges in managing the Epstein fallout.
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Also Read: MAGA Now Scrutinize Trump Over Epstein Client List Failure
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