In the glittering ballrooms of 1990s New York, a brash real estate mogul named Donald Trump locked eyes with Jeffrey Epstein—a mysterious financier with a penchant for beautiful, often underage women—and saw not just a friend, but a mirror of his own ambitions.h

In the high-society scene of 1990s New York and Palm Beach, Donald Trump—a prominent real estate developer and celebrity—and Jeffrey Epstein—a rising financier—formed a close social friendship that lasted over a decade, frequenting the same exclusive parties, events, and venues.

Their bond began in the late 1980s, with Trump later stating in a 2002 New York Magazine profile that he had known Epstein for 15 years, calling him a “terrific guy” who was “a lot of fun to be with.” Trump added: “It is even said that he likes beautiful women as much as I do, and many of them are on the younger side.” At the time, Epstein’s criminal activities involving underage girls were not publicly known.

The two were often photographed together at glamorous gatherings, including a 1992 party at Mar-a-Lago (Trump’s Palm Beach resort) where archived video shows them chatting and gesturing toward women, as well as events in New York like the 1993 opening of the Harley Davidson Cafe and Trump’s wedding to Marla Maples that December (where Epstein attended).

They also socialized with Ghislaine Maxwell (Epstein’s associate, later convicted of sex trafficking) and others, such as at a 2000 Mar-a-Lago event with Trump’s then-girlfriend Melania Knauss.

Flight logs from the 1990s show Trump flew on Epstein’s private jet multiple times (at least eight between 1993–1997, per 2025 document releases), often short trips between Florida and New York, sometimes with family members or Maxwell—no evidence links these to Epstein’s island or crimes.

The friendship ended acrimoniously around 2004–2007, reportedly over a real estate bidding war (Trump outbid Epstein for a Palm Beach mansion) and allegations Epstein recruited staff from Mar-a-Lago. Trump later banned Epstein from the resort and distanced himself, stating in 2019 he was “not a fan” and hadn’t spoken to him in 15 years. Trump has consistently denied any knowledge of or involvement in Epstein’s criminal activities, which emerged publicly in 2005–2008. No charges or substantiated allegations of wrongdoing by Trump have arisen from investigations or document releases through 2026.