‘He's a lot of fun to be with': Trump and Epstein were close friends for 15 years
The relationship would eventually break down, the men falling out over a bidding war on a property in Florida. And after Epstein was convicted of child sex offences in 2008, Trump distanced himself from the financier, claiming he was 'not a fan' and wondering, in recent days, why his supporters would 'waste time and energy' on demanding that FBI and Department of Justice files on Epstein be released.
But photos, videos and anecdotes paint a picture of a close friendship, of two middle-aged men who repeatedly partied together both alone and with their partners, including with Melania Knauss, who would go on to become Trump's third wife.
Related: How the Jeffrey Epstein row plunged Maga world into turmoil – a timeline
'I've known Jeff for 15 years. Terrific guy,' Trump told New York magazine in 2002. '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.'
Trump's insight into Epstein's predilections would be proved true in macabre fashion, when Epstein was found guilty in 2008 of sexually abusing girls aged between 14 and 17 years old. When Epstein was charged with sex trafficking of minors, in 2019, Trump attempted to play down their relationship, insisting: 'I knew him like everybody in Palm Beach knew him.' Trump said the pair had fallen out years earlier, and claimed: 'I was not a fan of his.'
But during the 15 years that the men were friends, there were plenty of incidents that displayed Trump and Epstein's closeness.
The New York Times reported that in 1992, George Houraney, a Florida-based businessman, had organized a 'calendar girl' competition at Mar-a-Lago, Trump's private members' club where he would later live full-time.
Houraney flew more than two dozen women to Mar-a-Lago, but he had a surprise when they arrived.
'I arranged to have some contestants fly in,' Houraney told the Times. 'At the very first party, I said, 'Who's coming tonight? I have 28 girls coming.' It was him and Epstein.'
Houraney said he was surprised. 'I said: 'Donald, this is supposed to be a party with VIPs. You're telling me it's you and Epstein?''
It ended up being just Trump and Epstein.
Back then, Trump made no secret of the friendship. He was pictured with Epstein at events and parties from New York to Florida.
Video from a party at Mar-a-Lago in 1992 shows the pair in conversation as a dance track booms through the speakers. Trump whispers something into Epstein's ear, prompting Epstein to bend over laughing. The tape was aired by NBC News during Trump's first term as president, and the news channel reported that it showed both Trump and Epstein pointing out women, while at one point Trump gestures to a woman and says: 'Look at her, back there … she's hot.'
In 1993 Stacey Williams, then a professional model, visited Trump at Trump Tower with Epstein. On arrival, she would later tell the Guardian, Trump put his hands 'all over my breasts', waist and buttocks while Trump and Epstein smiled at each other, in what she believed was a 'twisted game' between the two men.
'It became very clear then that he and Donald were really, really good friends and spent a lot of time together,' Williams said in 2024. Karoline Leavitt, then a spokesperson for Trump's election campaign, described Williams's accusations as 'unequivocally false. It's obvious this fake story was contrived by the Harris campaign.'
What is undeniable is that the men maintained their relationship through the 1990s. They were photographed at Mar-a-Lago, and the same year were pictured together at a Victoria's Secret Angels event in New York. The relationship endured. Photos show Trump and Epstein with Melania Trump and Ghislaine Maxwell at an event in 2000. Maxwell would be sentenced to 20 years in prison in 2022 for procuring teen girls for Jeffrey Epstein for him to abuse – when she was charged with the crimes Trump responded: 'I just wish her well, frankly.'
The Wall Street Journal also reported on Thursday that Trump allegedly wrote Epstein a birthday card as part of a 50th birthday album organized by Ghislaine Maxwell in 2003. The letter was fashioned in the shape of a woman's body, and consisted of an imaginary dialogue between the two, the Journal said.
'Donald: We have certain things in common, Jeffrey.
Jeffrey: Yes, we do, come to think of it.
Donald: Enigmas never age, have you noticed that?' it read, with Trump's signature squiggled as it were pubic hair on the outline of the body.
Trump once believed Epstein to be a terrific guy, but he wasn't the only one who talked up the friendship. Years later Epstein would tell the journalist Michael Wolff that he had been Trump's 'closest friend for 10 years', in audio tapes published on Wolff's Fire and Fury podcast last year. Epstein also told Wolff that Trump liked to 'fuck the wives of his best friends', and said the first time he slept with Melania Trump was on Epstein's plane. Trump's camp claimed that Wolff was engaging in 'false smears' and 'election interference'.
The close friendship wouldn't last. The relationship soured in 2004, according to reports, after the pair became embroiled in a bidding war over a property in Palm Beach. In 2019, after Epstein was arrested, he said he had not spoken to Trump for 15 years. And despite his own close relationship with Epstein, Trump would go on to criticize others for the same thing, with Bill Clinton a particular source of deflection. Trump even shared a conspiracy theory that the former president was involved in Epstein's death – ironically sparking more intrigue in the case. Trump told reporters days after Epstein died:
'The question you have to ask is, did Bill Clinton go to the island? Because Epstein had an island. That was not a good place, as I understand it, and I was never there.' Trump adds: 'So you have to ask, did Bill Clinton go to the island? That's the question. If you find that out, you're going to know a lot.'
Clinton has denied going to Little St James island, which Epstein owned and later became synonymous with his crimes.
Trump now finds himself in a mess that is partly of his own making. The 'Epstein didn't commit suicide' conspiracy theory in which he dabbled quickly spread among rightwing commentators and media figures – many of whom demanded that documents related to Epstein's associates be released. When the Department of Justice failed to do so last week, it caused a rarely seen rift between Trump and his supporters, with Trump trying to brush off the saga, and his supporters angry at a perceived lack of transparency.
When Trump was elected in 2024, his supporters believed they were getting an administration that was anti-swamp and pro-open government, the kind of government that holds back no secrets. But looking back at Trump's statements on the Epstein files during the campaign, the president appeared to be leaving himself wriggle room.
Asked in an interview in September if he would declassify 'the 9/11 files' and 'the JFK files', Trump said yes. He is then asked if he would declassify 'the Epstein files', and initially said yes, but added:
'I think that [declassifying the Epstein files], less so, because you don't know – you don't want to affect people's lives if there's phoney stuff in there, because there's a lot of phoney stuff with that whole world.'
That wavering hasn't helped Trump, however, as he has attempted to quash his supporters' rebellion. In a cabinet meeting last week the president expressed surprise that people were 'still talking' about Epstein, later pleading with his base to 'not waste time and energy on Jeffrey Epstein, somebody that nobody cares about'.
How wrong he was. It turns out loads of people care about Jeffrey Epstein – particularly the people who support Trump. It was something Trump addressed on Wednesday, when he explicitly attacked his supporters in a post on Truth Social. 'My PAST supporters have bought into this 'bullshit,' hook, line, and sinker,' Trump wrote.
He added: 'I have had more success in 6 months than perhaps any president in our country's history, and all these people want to talk about, with strong prodding by the fake news and the success starved Dems, is the Jeffrey Epstein hoax. Let these weaklings continue forward and do the Democrats work, don't even think about talking of our incredible and unprecedented success, because I don't want their support anymore!'
Trump revels in his relationship with rank-and-file rightwing Americans, a relationship that has benefited him to the tune of two presidential terms and hundreds of millions of dollars. For the past decade it has seemed as if that relationship could endure any scandal, any broken promise.
But now, for the first time, Trump is finding cracks in his support. That past friendship with Jeffrey Epstein, the 'terrific guy' turned 'creep', could prove to be the president's undoing.
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He goes on to write critically that some schools are paying their athletes as much as $50 million this year from a combination of House settlement-related revenue share and third-party NIL. 'A national solution is urgently needed to prevent this situation from deteriorating beyond repair and to protect non-revenue sports, including many women's sports,' he writes. How he plans to do this is to direct various members of his cabinet — the attorney general, secretary of labor, secretary of education, etc. — to create policy around several concepts that the NCAA and conferences have been requesting help on from Congress for years. Among those: Protecting scholarships for non-revenue sports: The executive order, most notably, requires schools to maintain or even increase the number of scholarships they provide to non-revenue sports. This is geared to protect Olympic and women's sports that are at risk of elimination as schools direct more funding away from those and to the sports that generate the revenue like football and men's basketball. Those with $125 million or budgets (most of the power league schools) must provide more scholarship opportunities than they did last year, for instance. Those with budgets of $50 million must provide at least the same, as seen in a screen shot of the section here. Prohibit third-party, 'pay-for-play': You might call this the prohibition of booster collective pay to athletes, which, in a way, codifies the House settlement terms that prohibit collective pay to athletes if they are not deemed to be for legitimate endorsement or commercial opportunities. This issue is at the heart of negotiations among attorneys that is expected to result in a resolution soon that permits collectives to operate in a more open capacity than first thought. The executive order reinforces that provision in the House settlement. How does Trump plan to enforce these parameters? Well, that remains a bit murky, but he suggests in the order that members of his cabinet, as well as the Federal Trade Commission, have 30 days to create a plan on the enforcement of such, including potentially withholding federal funding for violators, opening up Title IX investigations, etc. Athlete employment: Trump directs the Secretary of Labor and the National Labor Relations Board to 'clarify the status of college athletes' — an obvious gesture toward the ongoing debate over courts potentially deeming college athletes as employees. As stated in the order preamble, Trump is against college athletes becoming employees and is clearly, with this directive, ordering cabinet members and the NLRB — he appoints the board — to rule that college athletes are students. Ironically enough, while many college leaders fight against employment, some of them believe collective bargaining is the only solution for the industry. Limited liability protection: This is another issue the NCAA and conferences have spent millions of dollars and six years lobbying for. They want to be protected from legal challenges so they can enforce their rules over things such as transfers, roster limits, booster pay — many of which have been deemed illegal by courts. Trump clearly disagrees with these court rulings, as he notes in the preamble. The order directs the attorney general and the chairman of the Federal Trade Commission to create policies to protect the 'long-term availability of college athletic scholarship and opportunities' when such is 'unreasonably challenged under antitrust' law. The attorney general and the FTC have 60 days to create such a plan, the order says. What are the immediate impacts of the executive order? The answer here is potentially … nothing. Trump's cabinet members — many of whom are quite busy with other more pressing matters — will need to make policy around these subjects. The specifics of that policy will dictate exactly how pivotal, if at all, this order is. What is a certainty is that whatever policies are created are not law and will likely be subject to legal scrutiny. Congressional action and court rulings are law in this country — not executive orders, legal experts tell Yahoo Sports. Baker even suggested this during his talk Thursday morning. 'You can't fix this stuff from executive order,' he said. 'Our focus for now really needs to be trying to get stuff dealt with through the legislative process.' As it turns out, Wednesday was a historic day for college sports with regard to congressional legislation. An all-encompassing federal college sports bill made its way out of committee for the first time since the NCAA's lobbying efforts began nearly six years ago. The SCORE Act, bipartisan but pro-Republican and NCAA-friendly legislation that many Democrats are against, received the necessary votes to advance out of committees and is eligible for debate on the House floor when members return in September from their traditional summer break. In many ways, the Score Act grants the NCAA and conferences similar protections as Trump's order. Above anything, Trump's executive order may get Congress to more urgently and swiftly push the bill across the goal line. However, if it does advance out of the House, the SCORE Act faces stiff pushback in a divided U.S. Senate, where at least seven Democrats are needed to overcome the filibuster and reach the 60-vote margin for any bill passage. The Senate, though, has been working toward the introduction of its own legislation, led by Sen. Ted Cruz, who, much like Trump, has made college sports regulation a priority. He's been in negotiations now for months with several Democrats, most notably Chris Coons, Richard Blumenthal and Cory Booker. No agreement has been reached despite more than a year of intense talks. Will Trump's executive order change that? It's one of many questions on the topic that remains a mystery.
