Donald Trump’s past relationship with convicted sex offender Jeffrey Epstein is drawing fresh attention after the former U.S. president denounced a Wall Street Journal report claiming he once sent Epstein a sexually suggestive birthday letter as “fake news.” As public pressure mounts for the release of all government files related to Epstein’s crimes and death, Trump’s past connection to the disgraced financier is under renewed examination.
Parties, Jets, and Allegations
Trump and Epstein are believed to have been acquaintances since the early 1990s, when Trump was a wealthy real estate mogul known for his flamboyant lifestyle. In 1992, they were filmed partying together with NFL cheerleaders at Trump’s Mar-a-Lago resort in Florida. That same year, Epstein was reportedly Trump’s only guest at a “calendar girl” event hosted by Trump featuring over two dozen women.
Court documents and flight records show Trump flew on Epstein’s private jet at least seven times during the 1990s. Trump has denied these claims, saying in 2024 that he was “never on Epstein’s plane.”
In a 1993 incident, The New York Times reported that Trump allegedly groped model Stacey Williams after Epstein introduced them at Trump Tower — an allegation Trump has denied. Separately, Trump has faced accusations of sexual misconduct from about 20 women over the years. In 2023, he was found civilly liable for sexually abusing and defaming journalist E. Jean Carroll.
‘Terrific Guy’ to Public Fallout
Epstein’s primary accuser, Virginia Giuffre — who died by suicide in 2025 — claimed she was first approached for Epstein’s alleged trafficking network in 2000 while working at Mar-a-Lago. She said Ghislaine Maxwell recruited her there. Maxwell was convicted in 2022 for assisting Epstein in the sexual abuse of underage girls.
Despite this backdrop, Trump described Epstein as a “terrific guy” in a 2002 New York Magazine profile, adding that Epstein liked beautiful women “on the younger side.”
In 2003, according to the Wall Street Journal, Trump allegedly sent Epstein a graphic birthday message, drawing a naked woman and signing “Donald” in a way resembling pubic hair. The letter reportedly read: “Happy Birthday – and may every day be another wonderful secret.” Trump has dismissed the report as fake.
Denials and Distance
Trump claimed to have severed ties with Epstein in 2004 after they competed to buy a mansion in Florida — a deal Trump eventually won. He later said the two had not spoken in 15 years.
Following Epstein’s 2008 conviction and subsequent 2019 arrest on new sex trafficking charges, Trump, then president, tried to further distance himself. “I wasn’t a fan,” he told reporters in 2019.
Epstein’s death later that year — officially ruled a suicide — sparked widespread conspiracy theories. Trump himself promoted the idea that powerful figures, including Bill Clinton, were somehow involved. Ironically, these same conspiracy theories have begun to cast a shadow over Trump’s own political legacy.
As calls grow louder for transparency regarding Epstein’s network and connections, Trump’s past association with him remains a controversial and politically sensitive issue — one the former president continues to dismiss as fabricated or exaggerated by his opponents.
