Donald Trump and Jeffrey Epstein’s relationship has been documented for decades, but resurfaced this week after the reporter Michael Wolff alleged that Epstein once showed him photos of Trump—who denies this account—posing with topless “young girls.”
Trump, 78, has made some glowing comments about Epstein over the years and once remarked his former pal had a penchant for “younger” women in a 2002 interview with New York Magazine. More recently, Trump referred to the sex trafficker as a “good salesman” in a podcast appearance with Lex Friedman.
Far outnumbering Trump’s praise of the late Epstein, however, has been his hard-and-fast distancing from the former financier since his arrest on July 6, 2019—two weeks before authorities say he died by suicide while in custody.
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Below is some of Trump’s comments—the good, bad, and ugly—about Epstein over the years.
‘Terrific guy’ who likes his women young
Perhaps Trump’s most infamous comments about Epstein came in 2002 when he spoke to a New York magazine reporter for a profile that was detailing the life of his fellow New York City native who, like Trump, frequented Palm Beach.
Trump told a reporter over the phone that he’d known Epstein for 15 years. Trump then described Epstein, 49 at the time, as being a “terrific guy” who “likes to have fun.”
Trump’s next line, however, is likely the one he regrets the most.
“It is even said that he likes beautiful women as much as I do,” Trump said, “And many of them are on the younger side.
Trump’s quote in the two-decade-old piece closed with, “No doubt about it—Jeffrey enjoys his social life.”
It was during this period where, according a source who spoke to The Washington Post, Trump and Epstein were so close they “were each other’s wingmen.”
A ‘bitter’ real estate rivalry
Just two years after he sang Epstein’s praises to a magazine reporter, things reportedly got nasty between Trump and Epstein during a “bitter” bidding war for a prime property on the Palm Beach coast, reported the Post.
The property, the Maison de l’Amitie as it was named, had been put up for auction in 2004 after it was seized from the bankrupted nursing home magnate Abe Gosman.
The Post explained that Trump wanted to buy the estate and flip it for a profit, while Epstein wanted to make the property his permanent home. While their reasons for pursuing the waterfront mansion differed, their desire to win at all costs reportedly pushed them to bash each other behind closed doors.
The trustee overseeing the auction, Joseph Luzinski, told the Post that each man tried to convince him the other didn’t have the funds to afford the estate.
Luzinski told the Post: “It was something like, Donald saying, ‘You don’t want to do a deal with him, he doesn’t have the money,’ while Epstein was saying: ‘Donald is all talk. He doesn’t have the money.’ They both really wanted it.”
Trump drove up the price in a bidding war on auction day, which was mere months before Epstein was first investigated by Florida cops for sexually abusing a 14-year-old girl.
Trump won the auction and purchased the property for $41.35 million to outbid a third potential buyer and Epstein, whose final bid was $38.6 million. There were no public reports of interaction between Trump and Epstein after the sale.
‘He’s a real creep’
Trump’s private bashing of Epstein wasn’t limited to the real estate rift. Trump also disparaged Epstein to a 2016 campaign aide as being a “real creep,” the Post reported. Trump also reportedly claimed to that aide during his 2016 campaign that he banned Epstein from Mar-a-Lago because he’d acted inappropriately toward a girl there.
The earliest report of the supposed Mar-a-Lago ban appears to have come from the New York Post in 2007. The tabloid quoted a source as saying: “[Epstein] would use the spa to try to procure girls. But one of them, a masseuse about 18 years old, he tried to get her to do things. Her father found out about it and went absolutely ape-[bleep].”
Epstein denied that he was banned from Mar-a-Lago and told the paper that he’d been invited to an event there “recently.”
Trump, who records show flew on an Epstein jet at least seven times in the ‘90s between New York and Palm Beach, has repeatedly pointed to the club ban as proof that he distanced himself from Epstein at the first sign of red flags.
An uncomfortable pool party
Roger Stone, a former adviser to Trump, gave a foreboding account of what Trump claimed to have witnessed at Epstein’s Palm Beach estate.
In Stone’s 2016 book, The Clintons’ War on Women, he wrote that Trump noted to a Mar-a-Lago member after a visit to Epstein’s home that a crowd of girls in the financier’s pool appeared to be underage.
“The swimming pool was filled with beautiful young girls,” Trump said, according to Stone. The book said Trump then jokingly added: “‘How nice,’ I thought, ‘he let the neighborhood kids use his pool.’”
Stone reportedly said in a later appearance on Lindell TV that Trump left Epstein’s place after just 15 minutes because he was “uncomfortable with the mix of younger women and the limited number of men.” It’s unclear when Trump’s supposed visit to Epstein’s home took place.
Stone’s book said Trump was invited to Epstein’s infamous private island, but always declined.
Another account from Trump that dates to 2016 came via San Nunberg, an ex-campaign aide. Nunberg told The New York Times that he questioned Trump during his first campaign about his ties to Epstein. The then-candidate Trump reportedly dismissed the connection as being dealt with.
“I kicked him out of the clubs when this stuff became public,” Trump said, according to Nunberg. “And I made sure NBC knew.”
Reacting to Epstein’s arrest
Epstein was arrested mid-way through Trump’s presidency on July 6, 2019.
Trump was immediately called on to answer questions about his relationship with Epstein, to which he asserted that he had a falling out with him and hadn’t spoken to him for 15 years.
Pressed about their relationship on July 9, 2019, Trump responded to a reporter: “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. 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. I was not—yeah, a long time ago, I’d say maybe 15 years. I was not a fan of his. That I can tell you. I was not a fan of his.”
Trump echoed that sentiment on other occasions, including three days later when he was asked if he had knowledge of Epstein’s crimes.
“No, I had no idea,” Trump said on the White House’s south lawn. “I had no idea. I haven’t spoken to him in many, many years. But I had—I didn’t have no idea.”
Trump added in response to another question that day: “Jeffrey Epstein was not somebody that I respected. I threw him out. In fact, I think the great James Patterson, who is a member of Mar-a-Lago, made a statement yesterday that, many years ago, I threw him out.”
Well wishes for Epstein’s procurer
While Trump was spoken harshly about Epstein, he had much nicer words in July 2020 for his longtime procurer, Ghislaine Maxwell, after she was arrested in connection to Epstein’s crimes.
“I wish her well, frankly,” Trump said of Maxwell. “I’ve met her numerous times over the years, especially since I lived in Palm Beach, and I guess they lived in Palm Beach. But I wish her well, whatever it is.”
Trump was harshly criticized for the comment, which came just months prior to the 2020 election. Those criticisms didn’t stop him from doubling-down on giving his well wishes to Maxwell, however, with him repeating the line a second time in a televised interview with Axios a month later.
“Her friend, or boyfriend, was either killed or committed suicide in jail. She’s now in jail,” Trump said. “Yeah, I wish her well. I’d wish you well. I’d wish a lot of people well. Good luck. Let them prove somebody was guilty.”
Maxwell, 62, was sentenced in 2022 to two decades behind bars for conspiring with Epstein. Like Epstein, she was photographed alongside Trump at Mar-a-Lago in the early 2000s.
An Epstein jet on the campaign trail
Jeffrey Epstein stands in front of his Gulfstream G550 private jet.
U.S. Department of JusticeTrump’s campaign conceded to the Daily Beast in September that the former president had accidentally chartered a private jet to a fundraiser that once belonged to Epstein.
The gaffe, much like Wolff’s claim did this week, resurfaced Trump and Epstein’s relationship that goes back more than three decades.
A spokesperson for the Trump campaign explained that the jet was provided by a charter flight company after Trump’s plane was forced to be grounded for repairs. The temporary jet, which Trump flew on just once, had been outfitted with pro-Trump decals by the plane’s owner, who also claimed to know nothing about his Gulfstream G550’s sordid past.
“The campaign had absolutely no idea the aircraft we rented was previously owned by Mr. Epstein,” a Trump official told the Daily Beast, adding that Trump’s advisers only learned of the jet’s shady past once journalists contacted them.
Trump did not personally address the gaffe, just as he’s avoided speaking about the latest allegations—and leaked audio clip—brought forward by Wolff this week.
