It’s been six years since sex offender Jeffrey Epstein died by suicide while incarcerated, but his crimes—and his relationship with President Donald Trump—continues to loom large.
New emails released by House Democrats have brought their relationship back into the spotlight, with the late financier allegedly stating that Trump knew “about the girls” and that one of his alleged victims “spent hours” at his house with the President.
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During his campaign, Trump pledged to release Epstein’s so-called “list.” But ten months into his current term, his Administration’s efforts to do so have fallen short of many supporters’ expectations.
Trump has long maintained that his ties to Epstein were limited to social interactions common in Palm Beach, Florida, where both men owned property in the 1990s. Epstein’s mansion sat just down the road from Trump’s Mar-a-Lago estate, and the financier was reportedly a regular for several years at Mar-a-Lago.
“Well, I knew him like everybody in Palm Beach knew him. I mean, people in Palm Beach knew him. He was a fixture in Palm Beach,” Trump said in 2019 soon after Epstein was charged. “I had a falling out with him a long time ago. I don’t think I’ve spoken to him for 15 years. I wasn’t a fan.”
Here’s a timeline of Trump and Epstein’s relationship.
Late 1980s
Though it is not known when Epstein and Trump first met, Trump told New York magazine in 2002 that he had known Epstein for 15 years, which would date back to the late 1980s.
“I’ve known Jeff for fifteen years. Terrific guy,” the magazine reported Trump saying in a phone interview. “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.”
1992
NBC archival footage from 1992 shows Trump and Epstein at Mar-a-Lago, chatting and pointing at women dancing. In the background is Epstein’s associate Ghislaine Maxwell, later convicted of conspiring with Epstein in sex trafficking and sentenced in 2022 to 20 years in prison.
That same year, Florida businessman George Houraney told The New York Times he organized a “calendar-girl” party for Trump and Epstein featuring 28 women. Houraney later accused Trump of groping his girlfriend and business partner Jill Harth during a business presentation. Harth filed a 1997 sexual-assault lawsuit that she later dropped after settling a separate case with Trump, according to the AP. Trump did not comment on the reporting at the time.
1993-1997
Flight logs from Epstein’s private jet show Trump, then-wife Marla Maples, and their daughter Tiffany flying several times in the mid-1990s. Those records, released earlier this year by Attorney General Pam Bondi, had been public previously.
Bondi’s release also included Epstein’s “black book,” which had also previously been published. The book featured names of prominent people including Trump, former President Bill Clinton, and Andrew Mountbatten Windsor, formerly Prince Andrew.
As The New York Times reported, inclusion in the book did not necessarily indicate personal or business ties.
2003
In September, the House Oversight Committee released pages from a birthday book compiled for Epstein’s 50th birthday. Among the entries was a lewd sketch and note allegedly signed by Trump that read, “Happy Birthday—and may every day be another wonderful secret.”
Read More: Epstein’s Full ‘Birthday Book’ Has Been Released. Here’s What’s Inside
The president has repeatedly denied writing the letter and sued the Wall Street Journal’s parent companies, Dow Jones and NewsCorp, Rupert Murdoch, and two reporters for defamation after the paper reported on the letter.
“As I have said all along, it’s very clear President Trump did not draw this picture, and he did not sign it,” Leavitt wrote on X after the letters were released. “President Trump’s legal team will continue to aggressively pursue litigation.”
2004
Trump and Epstein are said to have fallen out in 2004 over a business deal related to an oceanfront property called the Maison de L’Amitié in Palm Beach, according to the Washington Post, with Trump ultimately offering the higher bid. Joseph Luzinski, the bankruptcy trustee, told the Post that the two faced-off as “two very large Palm Beach egos going at it.”
A year later, Florida police opened a sex-crimes investigation into Epstein that led to his 2008 conviction on state prostitution charges after he negotiated a plea deal granting him federal immunity. His attorney at the time, Alex Acosta, later served as Trump’s Labor Secretary.
2011
On Nov. 12, The House Oversight Committee released email correspondence from Epstein spanning 2011, 2015, and 2019 as part of a 23,000-document review of materials from the Epstein estate.
In a 2011 exchange, Epstein allegedly discussed Trump with Ghislaine Maxwell, referring to him as “the dog that hasn’t barked.” Maxwell replied, “I have been thinking about that…” Epstein also claimed that one of his victims, whose name was redacted, had spent “hours” with Trump at his home.
A White House statement to TIME identified the woman as the late Virginia Giuffre, saying she had “repeatedly stated that President Trump was not involved in any wrongdoing whatsoever and couldn’t have been friendlier to her in their limited interactions.”
2015
In a December 2015 email exchange, author Michael Wolff told Epstein that CNN planned to ask Trump about their relationship. When Epstein asked how he should respond, Wolff advised that he “let him hang himself.” He added that if Trump denied any connection, Epstein could later use it “to generate a positive benefit for you, or, if it really looks like he could win, you could save him, generating a debt.”
That June, Trump announced his first presidential campaign, which he would go on to win the following year. Wolff later chronicled Trump’s early presidency in his 2018 bestseller Fire and Fury: Inside the Trump White House. Wolff is now in a legal dispute with First Lady Melania Trump after she threatened a $1 billion lawsuit over comments he made linking her to Epstein.
2017
After Epstein’s 2008 conviction, Trump sought to distance himself from the financier.
Trump has said the friendship ended after Epstein recruited young women who worked at Mar-a-Lago for his own use. “He took some of the people who worked for me,” Trump told reporters in July. “Once he did that, that was the end of him.”
Trump Organization attorney Alan Garten said in 2017 that Trump had “no relationship with Mr. Epstein and had no knowledge whatsoever of his conduct.”
2019
The most recent emails obtained by the House Oversight Committee date from January 2019, during Trump’s presidency. In one, Epstein allegedly wrote to Wolff referencing a redacted victim’s name and the word “Mar-a-Lago.” The message continues: “Trump said he asked me to resign—never a member ever… of course he knew about the girls, as he asked Ghislaine to stop.”
The post Inside Trump and Epstein’s Long, Complicated Relationship appeared first on TIME.
