Trump’s Friendship With Jeffrey Epstein: Everything We Know

Author Michael Wolff made several salacious claims about Epstein and Trump on the October 31 episode of his podcast Fire and Fury, which he co-hosts with former Condé Nast editor James Truman. On November 2, The Daily Beast published another tape of Epstein talking with Wolff in which he claimed, “I was Donald’s closest friend for 10 years.”

On his podcast, Wolff, who wrote three books about the Trump administration, said Epstein had showed him about half a dozen photos of Trump with “topless young women” sitting in his lap, which were taken in the late ‘90s at Epstein’s Palm Beach home. The Daily Beast reported:

Wolff said of the photos, “They were with Trump at Epstein’s Palm Beach house sitting around the pool with these young girls, and the young girls are topless.

“And in some of the pictures, they’re sitting in his lap. I mean, and, and then there’s one I especially remember where there’s a stain, a telltale stain and on the front of Trump’s pants, and the girls are pointing at him and laughing.” Trump separated from his second wife Marla Maples in 1997 and began dating his third wife, Melania, in 1998.

Wolff said Epstein kept the photos in his safe, which was seized by the FBI when they raided his homes in July 2019. The author said that during the Trump administration, the convicted sex offender was “utterly preoccupied with Trump, and I think, frankly, afraid of him.”

In the same episode, Wolff claimed that in the ‘90s Trump and Epstein were “very competitive” especially when it came to women, and “shared a girlfriend” at one point, per Newsweek. Wolff also said that at one point they “had a competition about who would be the first one who would sleep with Princess Diana,” though he added, “Now, I don’t think that ever happened.”

Wolff also played a purported recording of Epstein talking with him about Trump’s White House team, which he said was made in a New York restaurant in 2017. Wolff claimed he his recordings of Epstein discussing Trump total around 100 hours.

In the recording published on November 2, which Wolff said was recorded in August 2017, Epstein says Trump is “charming,” but “He’s a horrible human being. He does nasty things to his best friends, best friends’ wives, anyone who he first tries to gain their trust and uses it to do bad things to them.”

Epstein also claims Trump liked to “fuck the wives of his best friends,” and describes his elaborate schemes for seducing his friends’ partners. Wolff says Epstein also bragged about his closeness to Donald and Melania by saying, “the first time he slept with her was on my plane,” the so-called “Lolita Express.” Flight logs show Trump flew on Epstein’s plane multiple times, though there is obviously no way to verify this specific claim.

Karoline Leavitt, the national press secretary for Trump’s 2024 election campaign, responded by pointing out that Wolff’s reporting has been questioned in the past. She told the Daily Beast:

Michael Wolff is a disgraced writer who routinely fabricates lies in order to sell fiction books because he clearly has no morals or ethics. He waited until days before the election to make outlandish false smears all in an effort to engage in blatant election interference on behalf of Kamala Harris. He’s a failed journalist that is resorting to lying for attention.

Less than two weeks before the 2024 election, former model Stacey Williams accused Trump of groping her in 1993 as Epstein looked on.

Williams had previously alluded to this on social media, but she publicly described the incident in detail for the first time during a Zoom call on October 21 organized Survivors4Harris, a group of sexual-abuse survivors supporting Kamala Harris.

Williams said that during a 1993 walk with Epstein, who she was dating, he suggested they stop into Trump Tower to visit Donald. She said on the call:

Moments later, Trump was greeting us. And he pulled me into him, and started groping me. He put his hands all over my breasts, my waist, my butt. And I froze. And I froze because I was so deeply confused about what was happening because the hands were moving all over me yet these two men were like smiling at one another and continuing on in their conversation. 

She said Epstein berated her afterward, and she came to feel that the groping was part of a “twisted game” between the two men. A short time later, Trump sent Williams a postcard from Mar-a-Lago via her agent. The Guardian published a photo of it on October 23.

Trump campaign press secretary Karoline Leavitt denied the story, telling The Guardian: “These accusations, made by a former activist for Barack Obama and announced on a Harris campaign call two weeks before the election, are unequivocally false. It’s obvious this fake story was contrived by the Harris campaign.”

Trump began palling around with Epstein in the late ’80s, but the depth of their friendship is a subject of debate.

Footage unearthed by NBC News in 2019 shows the two men joking around and ogling women during a party at Trump’s Mar-a-Lago resort in 1992.

Williams said that she met Epstein in 1992 and it was clear that “he and Donald were really, really good friends.” She said that while she was dating Epstein, he “mentioned Trump frequently. He was clearly a close friend and they were spending a lot of time together.”

Trump and Epstein were also photographed together in 1992 and 1997. The now famous image below shows Trump and then-girlfriend Melania Knauss partying with Epstein and Ghislaine Maxwell at Mar-a-Lago on February 12, 2000.

Photo: Davidoff Studios Photography/Getty Images

In 2002, the mogul told New York, “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.”

There is no evidence that Trump ever visited Little St. James, Epstein’s residence located in the U.S. Virgin Islands. Epstein allegedly trafficked and sexually abused women and girls there, which is why it was nicknamed “Orgy Island,” “Pedophile Island,” and “Island of Sin.”

Trump has denied that he ever visited Epstein’s island. But he’s been happy to fan similar unfounded conspiracy theories about about his political rivals. When asked in 2019 if he believes the Clintons were involved in Epstein’s death, Trump answered:

I have no idea. I know he was on his plane 27 times, and he said he was on the plane four times. But when they checked the plane logs, Bill Clinton, who was a very good friend of Epstein, he was on the plane about 27 or 28 times, so why did he say four times?

And then 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. So you have to ask, ‘Did Bill Clinton go to the island?’ If you find that out, you’re going to know a lot.

Like Trump, Clinton flew on Epstein’s plane. But none of the Epstein flight logs list either former president as passengers on Virgin Islands-bound flights. A Clinton spokesman said the former president “has never been to Little St. James” and his office has repeatedly said he “knows nothing” about Epstein’s “terrible crimes.”

Yes. Flight logs show Trump was on Epstein’s plane multiple times, though he has denied it.

Trump flew on Epstein’s private jet at least seven times between 1993 and 1997, according to flight logs made public during various court proceedings. As the Miami Herald reported in 2021, Trump was accompanied by his then-wife Marla Maples and two of his young children on some of these flights:

The flights were all between Palm Beach and New York City airports, with the June 1994 flight stopping at Ronald Reagan Washington Washington National Airport between Palm Beach and New York.

A woman named Marla, apparently Trump’s then-wife Marla Maples, is listed as joining him on the June 1994 flight, along with a Tiffany, apparently their then-infant daughter, and a nanny. Trump’s son Eric is listed as joining him on an August 1995 flight between Palm Beach and New York.

Nevertheless, in a January 2024 Truth Social post, Trump claimed “I was never on Epstein’s Plane, or at his ‘stupid’ Island.”

Bizarrely, it seems Trump unwittingly used Epstein’s plane during the 2024 campaign. The Miami Herald reported that the Trump campaign used a blue Gulfstream jet formerly owned by Epstein to travel to several campaign fundraisers after Trump’s private jet experienced mechanical problems on Friday, August 9, 2024:

Trump, enroute on his own private plane to a campaign event in Bozeman, Montana last week, unexpectedly landed in Billings because of mechanical problems, a campaign spokeswoman said. He and part of his staff then flew on a small charter to Bozeman for a rally Friday night. The next day, he switched to another larger Gulfstream with a serial number that matches a plane once owned by Epstein, his former neighbor in Palm Beach, the campaign confirmed.

“The campaign had no awareness that the charter plane had been owned by Mr. Epstein,” the spokeswoman said, adding that the charter was commissioned by a vendor that has often been used by the campaign. “We heard about the former owner through the media.”

Epstein’s old plane is now owned by Threshold Aviation Group, an Ontario, California-based company that offers private charter service. The Herald noted that the plane used by the Trump campaign was not the infamous “Lolita Express”; Epstein replaced that plane around 2017 and it “has since been destroyed.”

A Trump campaign official told the New York Times that it has used the private jet vendor for years, and will try to avoid using Epstein’s old plane in the future.

But Trump’s running mate, J.D. Vance, inadvertently generated more Trump-Epstein headlines just a few days later when he quipped to Fox News Sunday, “Giving Kamala Harris control over inflation policy, Shannon, it’s like giving Jeffrey Epstein control over human trafficking policy.”

In 2016 a woman who went by the pseudonyms Katie Johnson and Jane Doe in legal filings accused Trump of raping her in 1994, when she was 13, during an orgy held at Epstein’s home in Manhattan. She accused Epstein of raping her as well.

Three suits were filed over the same allegations; the first was dismissed for failure to properly state a claim, and the other two were voluntarily dismissed. The third case was withdrawn just days before the 2016 election, and the accuser canceled a press conference at the last minute. Her attorney, Lisa Bloom, said the woman had received death threats and, “She has decided she is too afraid to show her face … She is in terrible fear.”

The circumstances around the case were bizarre, as Vox summarized at the time:

It was the end of an incredibly strange case that featured an anonymous plaintiff who had refused almost all requests for interviews, two anonymous corroborating witnesses whom no one in the press had spoken to, and a couple of seriously shady characters — with an anti-Trump agenda and a penchant for drama — who had aggressively shopped the story around to media outlets for over a year.

Those shady characters — a former reality-TV producer who calls himself Al Taylor and a Never Trump conservative activist named Steve Baer — had been mostly unsuccessful in getting the media to bite. There are a few very good reasons for that, which the Huffington Post’s Ryan Grim succinctly summed up: Taylor and Baer have been really sketchy about the whole thing, and since the accuser is anonymous, journalists can’t do anything to verify her claims. The only journalist who has actually interviewed Johnson, Emily Shugerman at Revelist, came away confused and even doubting whether Johnson really exists.

Trump has been accused of sexual misconduct by more than 20 other women over the years; those women were not underage, and their allegations did not involve Epstein. In May 2023, a federal jury found Trump civilly liable for sexually abusing E. Jean Carroll in the mid-1990s and for defaming her when he denied her rape allegation in 2022. He was ordered to pay Carroll $5 million in damages and is currently appealing the verdict.

Trump has claimed that he and Epstein had a “falling out” years before the financier was first arrested in Palm Beach in 2005 after being accused of paying a 14-year-old girl for sex. (Though dozens of other underage girls accused Epstein of sexual abuse at the time, because of a 2008 plea deal, he served only 13 months in jail in a work-release program.)

There are reports that a battle over a choice Palm Beach property ended the Trump-Epstein friendship, but it’s unclear what exactly came between the two. Days after Epstein was arrested on federal sex-trafficking charges in 2019, Trump downplayed their relationship while speaking to reporters in the Oval Office. He said he merely “knew him like everybody in Palm Beach knew him,” adding, “I had a falling out with him. I haven’t spoken to him in 15 years. I was not a fan of his, that I can tell you.”

The newly unsealed documents are from Virginia Roberts Giuffre’s settled 2015 defamation lawsuit against Epstein’s former girlfriend Ghislane Maxwell, who is currently serving a 20-year prison term for trafficking women and girls for Epstein to sexually abuse. Giuffre is one of dozens of women, some as young as 14, whom Epstein allegedly abused.

Some documents were blacked out or sealed over privacy concerns when the suit was settled in 2017. But in December 2023, federal judge Loretta Preska ruled that most of the records would be made public since most of the names were already public. The first 40 exhibits, totaling 943 pages, were released on January 3, 2024. Another 17 documents were unsealed on January 8. Seven more documents were released on January 9. (Read about the other figures listed in the new Epstein documents here.)

On January 3, 2024, Trump’s spokesperson Steven Cheung offered a terse statement on the newly released documents, telling Newsweek that any claims about Trump’s relationship with Epstein had already been “thoroughly debunked.”

In short: not much. His name was mentioned four times in a May 2016 deposition of Johanna Sjoberg, one of Epstein’s alleged victims, who said she was around him from 2001 to 2006.

Sjoberg said that while flying on one of Epstein’s planes, they made an unplanned stop in Atlantic City and went to “one of Trump’s casinos.” She recalled that when she relayed the pilot’s message that they would need to land in New Jersey, “Jeffrey said, ‘Great, we’ll call up Trump and we’ll go to’ — I don’t recall the name of the casino, but — ‘we’ll go to the casino.’”

Later, Sjoberg said she never gave Trump a massage.

One of the 17 exhibits unsealed on January 8 references Trump — but he is only named in emails an Epstein victim sent to a journalist, which she provided no evidence to support and later recanted.

In emails exchanged with then–New York Post journalist Maureen Callahan in October 2016, Sarah Ransome made a number of explosive allegations against famous men, saying her friend had had sex with Bill Clinton, Prince Andrew, and Richard Branson on multiple occasions. Ransome also said she had videos of the encounters but could not share them without her friend’s permission.

All of the famous men named by Ransome denied her claims. A Virgin Group spokesperson said, “We categorically reject all allegations made by Sarah Ransome. In 2019 she admitted to The New Yorker that the ‘tapes’ had been ‘invented.’ Any suggestion that Sir Richard Branson was involved in a ‘sex tape’ is entirely false. The allegations are baseless and unfounded.”

In one of the now-recanted emails, summarized below by attorneys representing Alan Dershowitz, Ransome said her friend was one of “many girls” Trump had had sex with, claimed the friend regularly had sex with Trump at Epstein’s mansion, and shared other NSFW details about Trump’s sexual proclivities:

Ransome’s email that includes the claims about Trump appears later in the document and is partially cut off:

In the document, Dershowitz’s attorneys used the emails to portray Ransome as a liar, noting that she had made many outlandish claims to journalist Maureen Callahan, such as saying she’d reached out to the Russians for help and was “approached, by Special Agents Forces Men sent directly by Hilary [sic] Clinton herself, in order to protect her presidential campaign.” For example:

In her final email to Callahan, Ransome says she wants to “retract everything I have said to you and walk away from this.” Callahan never published a story related to her allegations.

Ransome then told The New Yorker in 2019 that she never had any videos. In her 2021 memoir, Silenced No More, Ransome explained why:

I also told her I had video evidence of public figures participating in Jeffrey and Ghislaine’s pedophile ring. I didn’t. I said I did because I was absolutely terrified that, once I went public with my story, Jeffrey and Ghislaine would find and kill me. I wanted to send them a message via the press: If you wage war on me, I will return fire by releasing my evidence. That would be my leverage, my way of protecting myself.

As ABC News noted, while Ransome was involved in various lawsuits against Epstein, no evidence supporting these claims appears in publicly available court records:

Ransome was deposed in 2017 as a witness in the Giuffre versus Maxwell litigation. No evidence supporting the allegations Ransome shared with the reporter was entered in the record of this case.

The lawsuit Ransome filed in 2017 under the pseudonym “Jane Doe 43” against Epstein, Maxwell and other alleged co-conspirators was settled the following year.

Neither Clinton, nor Trump, nor Branson was accused by Giuffre, or anyone else besides Ransome, of any wrongdoing in the course of Giuffre’s defamation lawsuit against Maxwell. 

Ransome gave a victim-impact statement in federal court at Maxwell’s sentencing that did not specifically mention Trump or anyone but Epstein and Maxwell.

Trump’s name appeared four times in a deposition of Giuffre taken on January 16, 2016. She said that while she’d heard Trump had been in Epstein’s home, she never saw him there herself, adding, “I don’t think Donald Trump participated in anything.”

Trump’s name was also mentioned in passing later in the deposition when he was described as one of Epstein’s famous friends.

Giuffre testified that she had been recruited into Epstein’s sex-trafficking ring by Maxwell, who approached her in 2000 when Giuffre was a 17-year-old spa attendant at Mar-a-Lago. Trump’s Florida resort comes up more than a dozen times in the newly released depositions, as Epstein and Maxwell are questioned about how they met Giuffre. But Giuffre has said she had no relationship with Trump beyond his being her employer.

The final batch of documents from Giuffre’s settled 2015 defamation lawsuit was released in January 2024. But other Epstein-related court records could still be made public.

On February 29, 2024, Florida governor Ron DeSantis signed legislation that paved the way for the release of grand-jury evidence and testimony from a 2006 Florida investigation into Epstein’s abuse of underage girls. The law says grand-jury records, which are usually secret, can be made public under limited circumstances.

The state’s initial investigation into Epstein’s sex ring has long been controversial, as New York’s Matt Stieb explained:

The state’s response to the initial investigation of Epstein’s sex ring in Florida has long been controversial. After police produced substantial evidence that Epstein was procuring and abusing girls, the state attorney’s office for Palm Beach County kicked the responsibility to a grand jury rather than charging Epstein directly. The grand jury ultimately led to one felony count against Epstein for soliciting prostitution — with no mention that the alleged victims were teenagers. Palm Beach police chief Michael Reiter published a letter he sent to five alleged victims stating that he did not believe “justice has been sufficiently served.” Reiter then brought the case to the FBI — which ultimately led to federal charges against Epstein and more controversy: Somehow, the financier scored a sweetheart deal signed by federal prosecutor Alex Acosta, which allowed him to leave jail six days a week for 12 hours at a time. (In 2019, Acosta resigned from his position as secretary of Labor after facing criticism for his role in the deal.)

Judge Luis Delgado ordered the records released on July 1, 2024, the day the new law went into effect. The 176-page transcript does not mention Trump or Mar-a-Lago. As the Washington Post reported, the “long sought-after records that show how prosecutors attempted to paint two young women who testified as criminals rather than victims of sexual abuse.”

In recent weeks many old Epstein court documents that mention his relationship with Trump have been circulating on social media. As Julie K. Brown, the Miami Herald reporter whose 2018 investigative series helped revive the criminal case against Epstein, clarified on X, these records were released years ago. This was confirmed by the Washington Post’s fact checker. The only new document released in July 2024 is the 176-page Florida grand jury transcript, which contains no new information about Trump.

False posts that claim prosecutors are “reconsidering bringing charges” against Trump “on child rape and molestation charges” have been circulating on Facebook recently. The story is attributed to the Associated Press, but on July 11 the AP said it never reported this.

Other fake posts that claim Michelle Obama tweeted about Trump being “mentioned in the Epstein docs” began circulating after her DNC speech. As Reuters explains, this is a post from a parody account. The former First Lady has never publicly commented on Trump and Epstein.

In a June 2, 2024, Fox & Friends interview, Trump was asked if he would declassify various federal files. He quickly answered “yes” when asked about documents on 9/11, the JFK assassination, and Epstein — but then backtracked on the sex trafficker.

“I guess I would,” Trump said. “I think [Epstein] less so because you don’t know, you don’t want to affect people’s lives if it’s phony stuff in there, because it’s a lot of phony stuff with that whole world. But I think I would, or at least—”

Interviewer Rachel Campos-Duffy tried to get Trump back on topic, but he continued musing about the Epstein files.

“Yeah, I don’t know about Epstein so much as I do the others. Certainly about the way he died,” Trump replied. “It’d be interesting to find out what happened there because that was a weird situation and the cameras didn’t happen to be working, etc., etc. But yeah, I’d go a long way toward that one.”

In an interview with podcaster Lex Fridman released September 3, 2024 Trump lightly praised Epstein when asked why he had so many powerful associates.

“He was a good salesman; he was, you know, a hailing, hearty type of guy,” Trump said. “He had some nice assets that he’d throw around, like islands.”

Trump did not commit to releasing more files on Epstein and his associates if reelected, but he said he’d “certainly take a look at it.”

“I’d be inclined to do the Epstein. I’d have no problem with it,” Trump added.

During an August 2023 interview, Tucker Carlson asked Trump if he believed Epstein had killed himself in jail. “I don’t know,” said Trump, who seemed more interested in bashing his former attorney general Bill Barr. After more prodding from Carlson, Trump said that he thought it was “possible” Epstein had been killed but that “I think he probably committed suicide.”

“Life with beautiful homes, beautiful everything, and all of a sudden he’s incarcerated and not doing well,” Trump said. “A lot of people think he was killed. He knew a lot on a lot of people.” Carlson confirmed that he was among those who believe Epstein “was killed,” and Trump replied that “a case could be made either way.”

No, Harris has not said anything about Epstein since becoming the Democratic presidential nominee. An image circulating online claims to show a screenshot of an X post in which Harris challenged Trump to a debate at Epstein’s townhouse. AFP factcheckers reported that, “the supposed X screenshot is fabricated and traces to a parody account; the vice president never shared such a post suggesting a connection between the two men.”