The alleged relationship between deceased sex trafficker Jeffrey Epstein and Donald Trump has become one of the most acute threats to the president’s power
Of all the scandals that have plagued Donald Trump throughout his lifetime in the public eye, his extensive and well-documented relationship with disgraced financier and sex trafficker Jeffrey Epstein presents the most clear and immediate danger to the president. While Trump has long denied any wrongdoing, the public contours of his association with Epstein paint a compelling — if frustratingly incomplete — picture of two men with years of shared history. Despite the president’s repeated claims that he and Epstein were mere social acquaintances who suffered a falling out of sorts over a young woman in Trump’s former employ, the steady drip of Epstein-related material from Congress, coupled with Trump’s conspicuously ardent reactions thereof, suggest a much more robust bond.
As the president fends off a growing bipartisan push for full governmental transparency on a scandal that shows little sign of abating, here is what we know about Donald Trump and Jeffrey Epstein’s long, complicated friendship.
1980s
While it’s unclear exactly when and where Trump and Epstein first met , Trump in a 2002 New York magazine interview said he’d known “terrific guy” Epstein “for fifteen years,” placing their initial point of contact in the mid-to-late 1980s. This was “around the time” of Trump’s 1985 purchase of his Mar-a-Lago estate in Palm Beach, Florida, where Epstein “was also living,” said Forbes. “In my mind,” Epstein was Trump’s “best friend, you know,” former Trump Plaza Hotel and Casinos COO Jack O’Donnell said to CNN in 2025.
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Trump and Epstein are filmed together during a party for a segment of Faith Daniels’ talk show, “A Closer Look,” about Trump’s life post-divorce from first wife Ivana. This “most widely circulated footage” of the pair shows the two men “evidently assessing” the women at the event, which included NFL cheerleaders in town for a game, Rolling Stone said. At one point, Trump is “seen gesturing to a woman” and tells Epstein, “Look at her, back there .… She’s hot,” NBC News said. Trump later “said something else into Epstein’s ear,” prompting the financier to “double over with laughter.”
Watch: Donald Trump and Jeffrey Epstein together in 1992 - YouTube
That same year, Florida-based businessman George Houraney flew 28 women to Trump’s estate for a “Calendar Girl” competition. Aside from the women, The New York Times said, the “only guests were Mr. Trump and Jeffrey Epstein.” Describing the incident to the Times, Houraney claims he said, “Donald, this is supposed to be a party with VIPs. You’re telling me it’s you and Epstein?’”
1993-2000
Trump and Epstein’s relationship continued through the ’90s, with the pair appearing in a photograph with Trump’s children Eric and Ivanka at a Harley Davidson Cafe opening in 1993. That same year, Epstein was photographed attending Trump’s second wedding to model Marla Maples. “I wish now I took more of him with Trump,” photographer Dafydd Jones said to CNN.“I had the job of photographing the Trump wedding, so I stood with the press and photographed him.”
In the subsequent four years, Trump would fly seven times on Epstein’s infamous aircraft, according to flight logs released during the trial of accomplice sex trafficker Ghislaine Maxwell.
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1997 also saw Trump photographed alongside Epstein at a Victoria's Secret party in New York City. In 2000, Trump, Epstein, Maxwell and soon-to-be Trump spouse Melania Knauss posed for a series of pictures together at a party at Mar-a-Lago also attended by Andrew Mountbatten-Windsor, the former Prince of England, who was stripped of his royal titles this year for sexual abuse and his relationship with Epstein.
Donald Trump poses with future wife Melania Knauss, Jeffrey Epstein and Ghislaine Maxwell
(Image credit: Davidoff Studios / Getty Images)
2000-2006
At the dawn of the new millennium, Trump and Epstein’s apparent friendship appeared to be going strong. In 2000, though, the seeds of discontent between the two patricians were planted when Virginia Giuffre, then a teenager working as a Mar-a-Lago spa attendant, was hired away from Trump by Maxwell and Epstein as a masseuse. Giuffre, one of Epstein and Maxwell’s “most well-known sex trafficking accusers,” took her own life in early 2025, The Associated Press said. While her allegations were not part of Epstein’s criminal prosecutions, she has become “central to conspiracy theories about the case.”
By 2002, however, Trump was still singing Epstein’s public praises, describing him as a person who was a “lot of fun to be with” and who “likes beautiful women as much as I do, and many of them are on the younger side,” to New York magazine.
The next year, the pair connected again for Epstein’s 50th birthday, for which Trump penned a poem written out and formatted to look like the body of a naked woman. Trump, who initially denied The Wall Street Journal’s report on the card’s existence, signed the message “Happy Birthday — and may every day be another wonderful secret.”
In 2004, whatever friendship existed between Trump and Epstein seems to have suffered a fatal blow when both men competed to purchase the enormous Maison de l’Amitie, an exclusive Palm Beach property that ultimately sold to Trump for more than $41 million. Two weeks after Trump obtained the property, Palm Beach police “fielded a tip that young women were seen coming and going from Epstein’s home,” said The Washington Post. Several months later, the local police received another complaint about Epstein, and by 2006 a grand jury had indicted him for solicitation.
2007
Trump finally “severed ties” entirely with Epstein in 2007, allegedly after the then-indicted financier “hit on the teenage daughter of a Mar-a-Lago member,” thereby damaging the “Trump brand of glitz and glamour,” The Miami Herald said. In 2025, Trump insisted that he’d made Epstein a persona non grata for “taking our people” from Mar-a-Lago, and has “long maintained” that his relationship with Epstein ended before the latter’s 2006 indictment, NPR said. But journalists who viewed Mar-a-Lago’s membership log said Epstein’s account at the club wasn’t closed until October 2007, “more than a year after he was indicted and released on bail,” said The Daily Beast.
2010
During a filmed deposition, Epstein is questioned about his relationship with Trump, and asked whether the pair had “socialized in the presence of females under the age of 18?” Epstein demurred from answering the question, citing his constitutional rights.
🚨🚨🚨 Watch Jeffrey Epstein plead his Fifth, Sixth, and 14th Amendment rights when asked if he and Donald Trump socialized with females under the age of 18 during a 2010 deposition:Q: Have you ever had a personal relationship with Donald Trump?A. What do you mean by "personal… pic.twitter.com/JyM5LYJ0C4July 24, 2025
2015-2019
Now-shuttered media publication Gawker obtained and published Epstein’s infamous “black book” of contacts, as well as the passenger logs for Epstein’s private aircraft, in 2015. Mentioned alongside international notables like Mick Jagger and Prince Andrew, Trump’s name, among others, appeared circled in the book by Epstein’s (since-deceased) housekeeper, “supposedly to identify them as potential ‘material witnesses,’” Vanity Fair said.
The following year, an unidentified plaintiff using the name “Katie Johnson” sued both Trump and Epstein multiple times, alleging the pair raped her in 1994 when she was a 13-year-old aspiring model. The suits were all eventually withdrawn or dismissed, and to date, it is “still not clear who Katie Johnson was, or if she ever existed,” said the San Francisco Chronicle.
In 2019, Epstein was arrested and held on federal sex trafficking charges. In response to questions about their relationship, Trump said he “was not a fan of his” in an effort to “further distance himself from his former friend,” said Rolling Stone. One month later, Epstein would be dead from an apparent jail cell suicide that has provided fresh fuel for Epstein-associated conspiracy theories in the years since.
2019-2024
Trump was reportedly “shocked” at Epstein’s jailhouse death, and “believed conspiracy theories would inevitably follow,” said The Daily Beast. Trump had the “same reaction I did,” former Attorney General Bill Barr said to congressional investigators during a deposition in the summer of 2025. “How the hell did that happen, he’s in Federal custody?”
The following year, Trump surprised observers with an “unusual detour” to offer “warm words” for Maxwell, who had been arrested that past July, the Times said. Asked whether he thought Maxwell might publicly name names connected with Epstein, Trump said, “I haven’t really been following it too much. I just wish her well, frankly.” The remarks “renewed attention” on the Trump-Epstein relationship, the Times said, particularly after the president had “sought to distance himself from the disgraced financier.”
In 2024, just days before Trump was to win reelection, model Stacey Williams alleged that Trump had inappropriately groped and fondled her during a visit to Trump tower with Epstein, whom she was casually dating at the time. “I had this horrible pit in my stomach that it was somehow orchestrated,” Williams said in an interview with The Guardian. “I felt like a piece of meat.”
Now
Since returning to the White House for the second time, Trump has gone out of his way to portray himself as maximally transparent regarding Epstein, even as his efforts highlight the degree to which his administration seems unwilling to act accordingly. Schisms within the Justice Department over the White House's handling of the case quickly threatened to overshadow the administration’s attempts to rerelease tranches of largely-public Epstein-related material to select right-wing influencers. At the same time, the White House’s conspicuous efforts to court a now-imprisoned Maxwell, and her congruent efforts to secure favorable treatment, have only accentuated Trump’s associations with her and Epstein.
In early November of 2025, after weeks of congressional wrangling and dueling public statements, lawmakers on the House Oversight Committee released huge swaths of Epstein-related items, including evidence that the disgraced sex trafficker remained in close contact with many in Trump’s orbit long after he and the president had fallen out. In the aftermath of those revelations, both the House and Senate passed a bill to release the extent of the government’s Epstein documents, with key exceptions for protecting witnesses, issues of national security and other sensitive matters. In a post on Truth Social, Trump confirmed he’d signed the bill into law, but stressed that “Democrats have used the ‘Epstein’ issue, which affects them far more than the Republican Party, in order to try and distract from our AMAZING Victories.”
Rafi Schwartz has worked as a politics writer at The Week since 2022, where he covers elections, Congress and the White House. He was previously a contributing writer with Mic focusing largely on politics, a senior writer with Splinter News, a staff writer for Fusion's news lab, and the managing editor of Heeb Magazine, a Jewish life and culture publication. Rafi's work has appeared in Rolling Stone, GOOD and The Forward, among others.
