Donald Trump and Jeffrey Epstein had a long-standing, complex relationship that began in the late 1980s and lasted through the 1990s into the early 2000s, marked by socializing in Manhattan and Palm Beach circles, shared parties, private jet flights, and mutual acquaintances.
- Beginnings in the Late 1980s: Trump first acknowledged knowing Epstein for around 15 years as of 2002, indicating they met circa 1987. At that time, Epstein was a financier and socialite in Palm Beach, and Trump a rising real estate mogul. Trump described Epstein as a "terrific guy" who "likes beautiful women as much as I do," many of whom were younger.
- Socializing and Shared Events: Throughout the 1990s, the two men partied together, including at Trump's Mar-a-Lago estate. They were seen in photos laughing together in 1992 and attended several events in the same social circles. Flight records show Trump took multiple rides on Epstein’s private jets between 1993 and 1997, and they were photographed together at high-profile events.
- Epstein’s Claim About Trump and Melania: Recordings from 2017 (released later) revealed Epstein claiming he was “Donald Trump’s closest friend” and alleging that Trump first slept with Melania Trump on Epstein’s private plane, the “Lolita Express.” Such claims have been strongly denied by Trump’s camp, describing them as false smears.
- Tensions and Fallout: The relationship reportedly soured before Epstein’s first arrest in 2006, with Trump later distancing himself from Epstein. Trump has denied any wrongdoing and any knowledge of Epstein's crimes, stating he is not a fan of Epstein anymore.
- Controversies and Recent Developments: In 2025, a Wall Street Journal article alleged Trump sent Epstein a risqué birthday card in 2003, which Trump denied and vowed to sue over. Epstein's extensive network and the handling of investigations have kept Trump’s relationship under scrutiny amid broader political and legal controversies.
This timeline illustrates a multifaceted friendship between two wealthy men linked by social status, mutual interests, and ultimately controversy given Epstein’s criminal convictions and Trump’s political prominence. While no direct involvement in Epstein’s crimes has been proven against Trump, their documented association continues to fuel public debate and investigation.
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