From parties to fallout: Real timeline of Trump and Jeffrey Epstein's relationship

The long and tangled relationship between former US President Donald Trump and the late financier Jeffrey Epstein returned to public scrutiny as Congress and the White House moved toward releasing the long-sealed 'Epstein files'. The House of Representatives and the Senate both voted to order the publication of government records relating to the Epstein investigation. Now, Trump has signed the 'Epstein Files Transparency Act', compelling the Justice Department to release its unclassified material. This shift has intensified interest in how close Trump and Epstein once were, how their relationship evolved, and how it ultimately collapsed. As questions accumulate about Epstein’s network and the institutions that failed to stop him, the nature of his ties with Trump remains a central part of the public conversation.

According to media reports, Trump and Epstein first became acquainted in the late 1980s, when both men owned property in Palm Beach, Florida. Their social circles overlapped heavily in the 1990s and early 2000s, and they reportedly visited each other’s real-estate properties. Both men hosted parties at their respective residences, including events at Trump’s Mar-a-Lago resort and gatherings at Epstein’s home. Epstein’s mansion stood only a short distance from Mar-a-Lago, and he was said to have been a regular guest there for several years.

Trump and Epstein were photographed together on numerous occasions during the 1990s. CNN has published images purportedly showing Epstein attending Trump’s wedding to Marla Maples. In 2002, Trump publicly described Epstein as a 'terrific guy', according to BBC reporting. Epstein, for his part, once claimed: “I was Donald’s closest friend for 10 years”. According to recordings obtained by The Daily Beast, Epstein even boasted that Trump first slept with Melania on his private aircraft, the so-called 'Lolita Express'. Previously released documents also included Trump’s details in Epstein’s 'black book', while flight logs confirmed that Trump flew on Epstein’s jet multiple times in the 1990s.

Trump has said their friendship deteriorated in the early 2000s, two years before Epstein’s first arrest. The White House has suggested that Trump 'kicked him out of his club for being a creep to his female employees', following allegations that Epstein behaved inappropriately toward a teenage girl at Mar-a-Lago.

Trump campaigned in 2024 on a promise to release the Epstein files. However, after entering the White House, he reversed course, withholding the records until it became clear Congress would vote to release them. Before shifting position, Trump ordered Attorney General Pam Bondi to open an investigation into Epstein’s links to prominent Democrats, including Bill Clinton. Bondi assigned the matter to a New York prosecutor, a decision that could affect how much of the forthcoming material is ultimately disclosed.

The 'Epstein files' refer to decades of documents from civil and criminal cases linked to Epstein, who died in 2019 while awaiting trial on federal sex-trafficking charges. The files span flight logs, emails, contact books and earlier investigative records. Names appearing in them, such as Trump, Clinton, Larry Summers, former Prince Andrew, Elon Musk, Michael Jackson, Tiffany Trump and Peggy Siegal, do not imply wrongdoing. But the files may offer unprecedented insight into Epstein’s associations and movements over nearly three decades.

Trump has repeatedly denied any involvement in Epstein’s criminal activities and has distanced himself from the late financier since the mid-2000s. However, as the release of government-held records draws closer, scrutiny of their past friendship is set to intensify.