Once seen as social allies, US President Donald Trump and the late pedophile Jeffrey Epstein shared a friendship that spanned over a decade.But as the GOP leader faces heat over his Epstein-era decisions, the spotlight is back on their scandal-laced ties — wild parties, private jet secrets, a bizarre birthday letter and explosive political fallout. Things that are now under the lens of both Democrats and Republicans.`Here’s a timeline of the unusual bond between Trump and Epstein:
1980s to Early 2000s: Friends in high places
Trump has publicly admitted that his friendship with Epstein began in the 1980s and lasted at least 15 years. In a 2002 interview with New York magazine, Trump said, “I’ve known Jeff for 15 years. Terrific guy. He’s a lot of fun to be with. It is even said that he likes beautiful women as much as I do, and many of them are on the younger side. No doubt about it — Jeffrey enjoys his social life.”During those years, the pair were seen together at several events. In 1992, Trump hosted a party at his Mar-a-Lago resort in Florida with NFL cheerleaders in attendance, where NBC footage shows him chatting with Epstein. They also attended a Victoria’s Secret “Angels” party in New York in 1997.
1993 to 1997: Flights on Epstein’s private jet
Trump’s name appears seven times in Epstein’s flight logs. He reportedly travelled on Epstein’s private plane four times in 1993, once each in 1994, 1995, and 1997. These trips took place between Palm Beach, New York, and Washington, DC. Trump acknowledged flying on Epstein’s jet, but he insisted he never travelled to Epstein’s private island or engaged in illegal activity. He has since pointed fingers at others, including former US President Bill Clinton, saying, “Got a lot of problems coming up in my opinion with the famous island with Jeffrey Epstein.” Trump was also listed in Epstein’s “little black book” of contacts, a now-infamous directory that included celebrities, politicians, and royalty.
2000: Mar-a-Lago and Virginia Giuffre ’s account
Trump’s Mar-a-Lago club reappeared in Epstein-related allegations when Virginia Giuffre, one of Epstein’s victims, said she was recruited there at the age of 16. Giuffre claimed she was reading a massage therapy manual when Ghislaine Maxwell approached her, offering a job as Epstein’s travelling masseuse. She alleged that she was later groomed and abused by Epstein and powerful men, including Prince Andrew. He denied the claims but stepped down from royal duties in 2019. Giuffre died by suicide in April 2025.
2003: The birthday letter controversy
The Wall Street Journal on Thursday reported that Trump sent Epstein a letter in 2003 for his 50th birthday, which included a sketch of a naked woman with the name “Donald” placed in a graphic area. The letter reportedly ended with the words: “Happy Birthday — and may every day be another wonderful secret.” Trump denied ever sending such a note. “I never wrote a picture in my life. I don’t draw pictures of women,” he told WSJ. “It’s not my language. It’s not my words.” The incident has triggered strong reactions. Trump has threatened to sue WSJ, Rupert Murdoch, and NewsCorp over the report, calling it “fake.” MAGA figures and loyalists have rallied behind him, with some calling the letter a forgery. Trump supporters argued he only writes with a black Sharpie, not typewritten notes.
2004: A falling out over property
Trump claimed the friendship with Epstein ended in 2004 after a real estate clash. Both men were bidding for a luxury Palm Beach mansion. Trump outbid Epstein, which reportedly led to a rift. By 2019, Trump said they had not spoken in 15 years and added, “I’m not a fan.” Shortly after the falling out, Palm Beach police received complaints about Epstein’s activities with underage girls, leading to his 2006 indictment and eventual plea deal in 2008.
2019: Epstein arrested again, dies in custody
Epstein was arrested again in 2019 on charges of sex trafficking minors. The case was reignited in part by The Miami Herald, which exposed how he had secured a lenient plea deal a decade earlier. He was accused of abusing dozens of girls, some as young as 14. While awaiting trial in a New York jail, Epstein died by suicide, according to officials quoted by The New York Times. His death sparked many conspiracy theories that continue to persist till date.
2020: Trump sends mixed signals on Maxwell
During the early part of his presidency, Trump appeared supportive of a full investigation into Epstein’s crimes. “I want a full investigation, and that’s what I absolutely am demanding,” Trump said in 2019. However, in 2020, he expressed sympathy for Ghislaine Maxwell, telling Axios’s Jonathan Swan, “I do wish her well. I’m not looking for anything bad for her.” Maxwell was later convicted in 2021 and is now serving a 20-year sentence.
2024–2025: Transparency promised , then pulled back
During the 2024 presidential campaign, Trump appeared open to releasing Epstein-related documents. “I guess I would,” he said on Fox News, before cautioning that “a lot of phony stuff” could damage innocent people’s reputations. After returning to office in 2025, Trump appointed justice department officials who had pledged to “get to the bottom” of the Epstein case. But in July, the department said no credible “client list” was found and dismissed blackmail rumours. Attorney General Pam Bondi confirmed that the video evidence Epstein held was downloaded material, not self-recorded footage of crimes. Still, Trump’s MAGA base grew frustrated, pushing for full disclosure. In response, Trump authorised Bondi to seek court approval to release grand jury testimony. He also blasted critics, saying: “He’s dead for a long time. He was never a big factor in terms of life. I don’t understand what the interest or what the fascination is, I really don’t.” He went further on Truth Social, calling the focus on Epstein “a scam” and called his own supporters “weaklings” for not letting the issue go.
