U.S. President Donald Trump continues to face scrutiny regarding his past relationship with Jeffrey Epstein, a convicted sex offender who died in jail in 2019 while awaiting trial on federal charges of trafficking underage girls. As new information about Epstein emerges, Trump and his administration have attempted to reshape the narrative surrounding their connection. Here is a timeline detailing the interactions between Trump and Epstein over the years.

In the 1990s, Trump, a prominent real estate developer, and Epstein, a hedge fund manager, became friends while moving in elite social circles in Manhattan and Palm Beach, Florida. They were seen together at various events, including Trump's wedding to Marla Maples. Flight logs indicate that Trump traveled on Epstein's private jet at least seven times, although none of these flights went to Epstein's private island.

In the early 2000s, as Trump gained national fame through his reality TV show, Epstein faced legal troubles for sexually abusing teenage girls. In a 2002 interview with New York magazine, Trump described Epstein as a "terrific guy" and noted their long-standing friendship. A leather-bound book gifted to Epstein for his 50th birthday included a message from Trump, which Trump later denied writing and is currently suing a newspaper for libel over its reporting on the letter.

The relationship between Trump and Epstein soured for reasons that remain unclear. Trump has suggested that the fallout was due to Epstein "taking people that worked for me" at Mar-a-Lago, while other accounts cite a bidding war over a mansion or Epstein's alleged harassment of a Mar-a-Lago member's daughter.

In 2008, Epstein avoided federal prosecution by pleading guilty to lesser state charges of soliciting prostitution from a minor, thanks to a controversial plea deal. This deal was overseen by Alexander Acosta, who Trump later nominated as his Secretary of Labor. Acosta resigned in 2019 after federal prosecutors revived the criminal case against Epstein.

In July 2019, Epstein was indicted on federal sex trafficking charges. When asked about his past comments on Epstein, Trump stated, "I don't think I've spoken to him for 15 years. I wasn't a fan." Epstein died in custody on August 10, 2019, with officials ruling his death a suicide.

In the 2020s, questions about Epstein's activities and his connections to Trump have persisted. Recently released emails from Epstein's correspondence suggest that Trump was aware of Epstein's conduct. In one email, Epstein wrote to Ghislaine Maxwell that Trump had spent hours with one of Epstein's victims and "knew about the girls."

The House Oversight Committee released these emails as part of a larger investigation into Epstein's activities. The emails have raised further questions about the nature of Trump's relationship with Epstein and the extent of his knowledge regarding Epstein's actions.

As the investigation continues, calls for the release of all Epstein-related documents have intensified, with some lawmakers demanding transparency regarding the findings. Trump has dismissed the inquiries as a political ploy, labeling them a "scam" and asserting that he has no connection to Epstein's criminal activities. Meanwhile, Maxwell is currently serving a 20-year prison sentence for her role in Epstein's trafficking operations.