By Alan Feuer and Matthew Goldstein July 20, 2025 — 2.37pm In the swirl of money and suntanned women that was their Palm Beach-and-Manhattan set, Donald Trump and Jeffrey Epstein spent nearly 15 years mingling side by side as public friends. There were lavish dinners with boldface names at Epstein’s mansion on New York City’s Upper East Side and raucous parties with cheerleaders and models at Trump’s private club and residence at Mar-a-Lago in Florida. In between, there were trips back and forth from Florida to New York on one of Epstein’s private jets. But behind the tabloid glamour, questions have lingered about what Trump’s long association with Epstein says about his judgment and character, especially as his allies have stoked sinister claims about Epstein’s connections to Democrats. Mar-a-Lago in 1996.Credit: Gamma-Rapho via Getty Images After their relationship ruptured, the disgraced financier ended up behind bars not just once, but two times, after being accused of engaging in sex with teenage girls. One of the young women who later said Epstein groomed and abused her was recruited into his world while working as a spa attendant at Mar-a-Lago. Another accuser recalled being eyed by Trump during a brief encounter in Epstein’s office, and claimed that Epstein had told Trump at the time, “She’s not for you”. Another woman has said that Trump groped her when Epstein brought her to Trump Tower in Manhattan to meet him. This past week, The Wall Street Journal reported that Trump gave Epstein a note for his 50th birthday in 2003 that included a sketch of a naked woman and a cryptic reference to a “secret” the two men shared. Trump has denied writing the message and filed a libel lawsuit Friday challenging the story. The New York Times has not verified the Journal report. Jeffrey Epstein and Donald Trump in Palm Beach, Florida in 1997.Credit: Getty Trump has never been accused of wrongdoing in connection with the Epstein case, and has said he had “no idea” that Epstein was abusing young women. In response to a request for comment about the president’s history with Epstein, Karoline Leavitt, the White House press secretary, said Trump had barred Epstein from his Mar-a-Lago club “for being a creep”. “These stories are tired and pathetic attempts to distract from all the success of President Trump’s administration,” she said in a statement. Trump and Epstein largely went separate ways after a falling-out around 2004, taking drastically different paths – one toward jail and suicide, the other toward further celebrity and the White House. Loading As criticism of the handling of Epstein’s case mounted over the years, some of Trump’s staunchest allies promoted theories that the government had covered up the extent of his network to protect what they have described as a cabal of powerful men and celebrities, largely Democrats. Now, that story has entangled Trump himself in what amounts to one of the biggest controversies in his second White House stint. The conflict has come primarily from his own appointees, who, after months of promoting interest in the files, abruptly changed course and said there was no secret Epstein client list and backed the official finding that Epstein had killed himself. Still, under mounting pressure from his own supporters to release the government’s files on Epstein, the president this past week ordered the Justice Department to seek the unsealing of grand jury testimony in the criminal case brought against Epstein in 2019 and one year later against his longtime partner, Ghislaine Maxwell, who is serving a 20-year sentence on a sex-trafficking conviction. She has asked the Supreme Court to consider her appeal. Even if they are released, the transcripts are unlikely to shed much light on the relationship between the two men, which did not figure prominently in either criminal case. What seemed to draw them together, according to those who knew them at the time, was a common interest in hitting on – and competing for – attractive young women at parties, nightclubs and other private events. Donald Trump and his future wife Melania, Jeffrey Epstein, and Ghislaine Maxwell in 2000.Credit: Getty Palm Beach Neighbours Trump and Epstein appear to have met around 1990, when Epstein bought a property about 3 kilometres north of Mar-a-Lago and set about staking a claim in Palm Beach’s moneyed, salt-air social scene. Trump, who had purchased Mar-a-Lago five years earlier, had already established his own brash presence in the seaside enclave as a playboy with a taste for gold-leaf finery. The two had much in common. Both were outer-borough New Yorkers who had succeeded in Manhattan. Both were energetic self-promoters. And both had reputations as showy men about town. In 1992, an NBC News camera captured the pair at a Mar-a-Lago party that featured cheerleaders from the Buffalo Bills, who were in town that weekend for a game against the Miami Dolphins. Donald Trump and Jeffrey Epstein at Trump’s Mar-a-Lago resort in 1992.Credit: Screengrab At one point in the footage, Trump can be seen dancing in a crowd of young women. Later, he appears to be pointing at other women while whispering something in Epstein’s ear, causing him to double over with laughter. Months later, when Trump hosted a party at Mar-a-Lago for young women in a so-called calendar girl competition, Epstein was the only other guest, according to George Houraney, a Florida-based businessman who arranged the event. Houraney recalled being surprised that Epstein was the only other person on the guest list. “I said, ‘Donald, this is supposed to be a party with VIPs,‘” Houraney told the Times in 2019. “You’re telling me it’s you and Epstein?’” Houraney’s then-girlfriend and business partner, Jill Harth, later accused Trump of sexual misconduct on the night of the party. In a lawsuit, Harth said Trump took her into a bedroom and forcibly kissed and groped her, and restrained her from leaving. She also said that a 22-year-old contestant told her that Trump later that night crawled into her bed uninvited. Harth dropped