Parties, jets and women: Inside the long Trump-Epstein friendship

Trump and Epstein largely went separate ways after a falling-out around 2004, taking drastically different paths – one toward jail and suicide, the other toward further celebrity and the White House.

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As criticism of the handling of Epstein’s case mounted over the years, some of Trump’s staunchest allies promoted theories that the government had covered up the extent of his network to protect what they have described as a cabal of powerful men and celebrities, largely Democrats.

Now, that story has entangled Trump himself in what amounts to one of the biggest controversies in his second White House stint.

The conflict has come primarily from his own appointees, who, after months of promoting interest in the files, abruptly changed course and said there was no secret Epstein client list and backed the official finding that Epstein had killed himself.

Still, under mounting pressure from his own supporters to release the government’s files on Epstein, the president this past week ordered the Justice Department to seek the unsealing of grand jury testimony in the criminal case brought against Epstein in 2019 and one year later against his longtime partner, Ghislaine Maxwell, who is serving a 20-year sentence on a sex-trafficking conviction. She has asked the Supreme Court to consider her appeal.

Even if they are released, the transcripts are unlikely to shed much light on the relationship between the two men, which did not figure prominently in either criminal case. What seemed to draw them together, according to those who knew them at the time, was a common interest in hitting on – and competing for – attractive young women at parties, nightclubs and other private events.

Palm Beach Neighbours

Trump and Epstein appear to have met around 1990, when Epstein bought a property about 3 kilometres north of Mar-a-Lago and set about staking a claim in Palm Beach’s moneyed, salt-air social scene. Trump, who had purchased Mar-a-Lago five years earlier, had already established his own brash presence in the seaside enclave as a playboy with a taste for gold-leaf finery.

The two had much in common. Both were outer-borough New Yorkers who had succeeded in Manhattan. Both were energetic self-promoters. And both had reputations as showy men about town.

In 1992, an NBC News camera captured the pair at a Mar-a-Lago party that featured cheerleaders from the Buffalo Bills, who were in town that weekend for a game against the Miami Dolphins.

At one point in the footage, Trump can be seen dancing in a crowd of young women. Later, he appears to be pointing at other women while whispering something in Epstein’s ear, causing him to double over with laughter.

Months later, when Trump hosted a party at Mar-a-Lago for young women in a so-called calendar girl competition, Epstein was the only other guest, according to George Houraney, a Florida-based businessman who arranged the event. Houraney recalled being surprised that Epstein was the only other person on the guest list.

“I said, ‘Donald, this is supposed to be a party with VIPs,‘” Houraney told the Times in 2019. “You’re telling me it’s you and Epstein?’”

Houraney’s then-girlfriend and business partner, Jill Harth, later accused Trump of sexual misconduct on the night of the party. In a lawsuit, Harth said Trump took her into a bedroom and forcibly kissed and groped her, and restrained her from leaving. She also said that a 22-year-old contestant told her that Trump later that night crawled into her bed uninvited.

Harth dropped her suit in 1997 after a related case filed by Houraney was settled by Trump, who has denied her allegations.

Trump and Epstein were spotted again at a 1997 Victoria’s Secret “Angels” party in Manhattan. The lingerie company was run by Leslie H. Wexner, a billionaire businessman who handed Epstein sweeping power over his finances, philanthropy and private life within years of meeting him.

Court records show that Trump was among those who got rides on Epstein’s private jet. Over four years in the 1990s, he flew on Epstein’s Boeing 727 at least seven times, largely making jaunts between Palm Beach and a private airport in Teterboro, New Jersey, just outside New York.

“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. No doubt about it – Jeffrey enjoys his social life.”

An Encounter at Mar-a-Lago

In 2000, court records show, Maxwell, a British socialite who had long been tied to Epstein, struck up a conversation with a 17-year-old girl outside a locker room at Mar-a-Lago.

Her name was Virginia Giuffre, and she was a spa attendant at the club, having gotten the job through her father, who worked there as a maintenance man. According to Giuffre, Maxwell offered her a job on the spot as a masseuse for Epstein after seeing that she was reading a book about massage, telling her that she did not need to have any experience.

She said that when she was brought to Epstein’s Palm Beach home, she found him lying naked on a table. Maxwell, she claimed, instructed her on how to massage him.

“They seemed like nice people,” she later testified, “so I trusted them.”

But over the next two years or so, Giuffre claimed that she was forced by Epstein and Maxwell to have sex with a series of famous men, including Prince Andrew, a member of the British royal family. The prince has denied the accusations and declined to help US prosecutors in their investigation of Epstein.

Giuffre, who died by suicide in Western Australia in April, always maintained that she was trafficked to the prince and other men, once telling the BBC that she had been “passed around like a platter of fruit” to Epstein’s powerful associates.

Some women who were in Epstein’s orbit have said they encountered Trump during this period.

One woman, Maria Farmer, who has said she was victimised by Epstein and Maxwell, described an encounter with Trump in 1995 at an office that Epstein once kept in New York City.

An art student who had moved to New York City to pursue a career as a painter, Farmer recalled in a 2019 interview that when she was introduced to Trump, he eyed her, prompting Epstein to warn him, “She’s not for you”.

Farmer’s mother, Janice Swain, said her daughter had described the interaction with Trump around the time it occurred.

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Stacey Williams, a former Sports Illustrated swimsuit model, has said she was groped by Trump when she was introduced to him by Epstein, whom she was dating at the time.

It was 1993, she said, and she was on a walk with Epstein on Fifth Avenue in Manhattan when he suggested that they pop into Trump Tower to say hello to Trump. Williams thought nothing of it at the time because, as she later put it, “Jeffrey talked about Trump all the time”.

After Trump greeted them in a waiting area outside his office, Williams said, he pulled her toward him, touching her breasts, waist and buttocks as if he was “an octopus”.

She said she later wondered whether she had been part of a challenge or wager between the two men.

“I definitely felt like I was a piece of meat delivered to that office as some sort of game,” she recalled to the Times last year. At the time, Trump’s presidential campaign denied that the episode had occurred, calling the allegations “unequivocally false” and politically motivated.

In an interview on Friday, Williams said she was upset to hear Trump referring to some of the Epstein story as a “hoax” and “boring” news. “I mean, it’s absurd,” she said of his speaking dismissively of the case.

Parting Ways

Eventually, in late 2004, Trump and Epstein ended up squaring off – this time, over a piece of real estate. It was the Maison de l’Amitié, a French Regency-style manse that sat along the ocean in Palm Beach.

The two hyper-competitive men each had their lawyers bid on the property. Ultimately, Trump came out ahead, purchasing it for $US41 million ($63 million).

There is little public record of the two men interacting after that.

Trump later told associates he had another reason for breaking from Epstein around that time: His longtime friend, he has said, acted inappropriately to the daughter of a member of Mar-a-Lago, and Trump felt compelled to bar him from the club. Brad Edwards, a lawyer who has represented many of Epstein’s victims, said Trump told him a similar story in 2009.

Not long after the standoff over the beachfront mansion, the Palm Beach police received a tip that young women had been seen going in and out of Epstein’s home.

Four months later, there was a more substantial complaint from a woman who claimed that her 14-year-old stepdaughter had been paid $US300 by Epstein to give him a massage while she was undressed. That led to a sprawling undercover investigation that identified at least a dozen potential victims.

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Epstein hired a team of top lawyers to defend him – including Alan Dershowitz, a Harvard law professor who would later represent Trump, and Ken Starr, the former independent counsel who investigated former president Bill Clinton’s affair with Monica Lewinsky.

The two men helped negotiate a lenient plea deal with R. Alexander Acosta, who was then the US attorney for the Southern District of Florida. Under the deal, Epstein pleaded guilty in 2008 to state charges of soliciting prostitution from a minor. In exchange, he was granted immunity from federal charges, as were all of his potential co-conspirators. He also had to register as a sex offender.

In the end, Epstein wound up serving almost 13 months in jail before he was released.

For his part, Trump largely steered clear of the controversy. But in February 2015, as he was gearing up for what would end up being a hard-fought election campaign against Hillary Clinton, he sought to connect Epstein to her husband, the former president.

Bill Clinton has “got a lot of problems coming up, in my opinion, with the famous island with Jeffrey Epstein,” Trump told Fox News host Sean Hannity during an appearance at the Conservative Political Action Conference, referring to Epstein’s private island where he resided and was suspected of trafficking underage girls. “A lot of problems.”

Clinton has denied visiting the island or having any knowledge of Epstein’s criminal behaviour, and has said he wishes he had never met him.

‘I Wasn’t a Fan’

In July 2019, Epstein was arrested again. Prosecutors from the public corruption unit of the U.S. attorney’s office in Manhattan charged him with sex trafficking and a conspiracy to traffic minors for sex.

Trump, then in his third year in the White House, immediately sought to distance himself from his old friend.

“I knew him like everybody in Palm Beach knew him,” Trump told reporters after the charges were revealed. “I mean, people in Palm Beach knew him. He was a fixture in Palm Beach. I had a falling out with him a long time ago. I don’t think I’ve spoken to him in 15 years. I wasn’t a fan.”

The new charges brought renewed scrutiny to the original plea deal. Days after Epstein’s arrest, Acosta – who had become Trump’s labor secretary – announced he would resign amid criticism of his handling of the case.

Speaking to reporters about Acosta’s decision, Trump reiterated that he had broken off his ties with Epstein “many, many years ago.” He added: “It shows you one thing: that I have good taste.”

Asked if he had any suspicions that Epstein was molesting young women, Trump replied, “No, I had no idea.”

The next month, after Epstein was found dead in his jail cell in Manhattan in what was later ruled a suicide, Trump weighed in again, reviving what was by then a years-old effort from his first campaign. He shared a social media post that tried to link the death to Bill Clinton.

Days later, when pressed about his unfounded claims of Clinton’s involvement, Trump did not let up, calling for a full investigation, even though he offered no facts to support his allegations.

“Epstein had an island that was not a good place, as I understand it,” he said. “And I was never there. So you have to ask: Did Bill Clinton go to the island?”

When Trump was asked about the arrest of Maxwell in the summer of 2020 on charges that included the enticement and trafficking of children, his answer left some of his own allies confused.

“I wish her well, whatever it is,” Trump said.

In recent weeks, right-wing influencers and Trump’s rank-and-file supporters expressed outrage over his administration’s conclusion that there were no revelations to share about the case – not least because some of the president’s top law enforcement officials, including Attorney-General Pam Bondi and FBI director Kash Patel, had promised to reveal more information about Epstein’s crimes.

Trump sought to quiet the demands, calling the Epstein scandal a “hoax” made up by his Democratic adversaries. He also described it as a subject unworthy of further scrutiny.

“Are you still talking about Jeffrey Epstein?” Trump asked reporters with exasperation at a Cabinet meeting July 8. “This guy’s been talked about for years.”