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() It’s no secret that President Donald Trump and convicted sex offender Jeffrey Epstein used to run in the same circle but how extensive was their relationship?
In 2002, Trump told New York magazine he’d known Epstein for 15 years and called him a “terrific guy.”
With an interest in fast-moving financing and beautiful women, the pair meshed in Palm Beach and attended similar social events at the close of the millennium, before an apparent real estate clash drove them apart in 2004.
In the following decades, Trump has continually tried to distance himself from Epstein’s infamy.
Most recently, he’s demanded people (including his loyal followers, which he’s dubbed “past supporters”) stop asking questions about the DOJ’s files on Epstein, despite previously pushing for more federal declassification.
The administration has requested that grand jury records regarding Epstein be unsealed, but a majority of the information people want is located in still-secret documents in the government’s possession.
Trump, Epstein socialized in high-profile circles together
From the 1980s to 2000s, the pair were in the same elite circle and were photographed together at events.
The pair, sometimes joined by now-first lady Melania Trump and Epstein’s ex Ghislaine Maxwell, frequented Trump’s Mar-a-Lago estate and Epstein’s Manhattan apartment.
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Portrait of American financier Jeffrey Epstein (left) and real estate developer Donald Trump as they pose together at the Mar-a-Lago estate, Palm Beach, Florida, 1997.(Photo by Davidoff Studios/Getty Images) -
From left, American real estate developer Donald Trump and his girlfriend (and future wife), former model Melania Knauss, financier (and future convicted sex offender) Jeffrey Epstein, and British socialite Ghislaine Maxwell pose together at the Mar-a-Lago club, Palm Beach, Florida, February 12, 2000. (Photo by Davidoff Studios/Getty Images) -
(From L) Political commentator Rogan O’Handley, aka DC Draino, TikToker Chaya Raichik, commentator Liz Wheeler and US conservative activist Scott Presler carry binders bearing the seal of the US Justice Department reading “The Epstein Files: Phase 1” as they walk out of the West Wing of the White House in Washington, DC, on February 27, 2025. The Trump administration has said it would release documents on late tycoon and convicted sex trafficker Jeffrey Epstein who was found dead in his prison cell in 2019. (Photo by Jim WATSON / AFP) (Photo by JIM WATSON/AFP via Getty Images) -
Acting U.S. Attorney for the Southern District of New York, Audrey Strauss, announces charges against Ghislaine Maxwell during a July 2, 2020, news conference in New York City. (Photo by Johannes EISELE / GETTY-AFP)
More privately, the two businessmen hosted two dozen women for a “calendar girl” competition at Mar-a-Lago in 1992, the New York Times reported.
Trump and Epstein were the only people there for the competition, George Houraney, a Florida-based businessman who ran American Dream Enterprise, told the outlet in 2019.
Trump’s reported birthday note to Epstein mentioned ‘wonderful’ secrets
Trump reportedly left Epstein a birthday message in 2003 mentioning that they have “certain things in common,” the Wall Street Journal reported. The note part of a larger book of notes from friends and acquaintances was typewritten inside a drawing of a naked woman’s outline.
“A pal is a wonderful thing. Happy Birthday and may every day be another wonderful secret,” the note ends.
Trump has since filed a $10 billion libel lawsuit against the WSJ and its reporters for the story.
“This is not me. This is a fake thing. It’s a fake Wall Street Journal story,” Trump told the Journal in an interview earlier this week. “I never wrote a picture in my life. I don’t draw pictures of women.”
Trump flew on Epstein’s jet seven times in four years
Flight logs released as evidence in the case against Epstein’s longtime associate, Maxwell, show that Trump flew on the financier’s private jet seven times between 1993 and 1997.
All the flights were between Palm Beach and New York City airports meaning, according to the logs, Trump never went to Epstein’s private island in the U.S. Virgin Islands.
Trump, Epstein allegedly had falling out in 2004
Chronicled by The Washington Post, a 2004 real estate debacle seems to have driven the two men apart.
Mutual want of an oceanfront Palm Beach mansion led to competing bids, threatened legal action and an end to their friendly public appearances.
In 2005, investigations into Epstein’s sexual misdoings kicked off. Trump testified against his onetime friend in 2009, said Brad Edwards, an attorney representing Epstein’s victims in a court filing.
Edwards maintains that Trump was “the only person who picked up the phone and said: ‘Let’s just talk. I’ll give you as much time as you want. I’ll tell you what you need to know,'” the Washington Post reported.
Epstein: I was Trump’s ‘closest friend for 10 years’
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American businessman and ex-president Donald Trump, Belgian model Ingrid Seynhaeve, and American businessman Jeffrey Epstein attend the Victoria’s Secret “Angels” party on April 28, 1997 in New York City. (Sonia Moskowitz/Getty Images). -
Businessman Donald Trump and financier Jeffrey Epstein attend a Victoria’s Secret Angels event sponsored by Rogers & Cowan at the club Duvet on 21st Street in New York City, New York on April 9, 1997. (Photo by Thomas Concordia/Getty Images) -
Ghislaine Maxwell and Jeffrey Epstein (Southern District of New York Court) -
LONDON, ENGLAND – JULY 17: A passerby stops to take a picture of a photograph of US President Donald Trump and convicted child sex offender Jeffrey Epstein as it is displayed after being unofficially installed in a bus shelter on July 17, 2025 in London, England. The satirical artist behind the stunt has previously targeted Elon Musk and Tesla. The US president is facing criticism from his usually loyal Republican “Make America Great Again” (MAGA) supporters over suggestions that the administration is hiding details of Epstein’s crimes to protect the high profile figures he associated with, which included Trump. Having previously suggested that there was reason to investigate a rumoured list of clients, Trump has now refered to it as a hoax and called those calling for an investigation “weaklings”. (Photo by Leon Neal/Getty Images)
During his first term, Trump told reporters he knew Epstein “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,” Trump said.
But Epstein himself described their relationship as something more meaningful in recordings obtained by and reported on by the Daily Beast.
In the 2017 interview with author Michael Wolff, Epstein described Trump as “charming” and “always fun,” but detailed Trump’s extramarital proclivities and his inability to be kind.
When asked by Wolff, “How do you know all this?” Epstein replied, “I was Donald’s closest friend
for 10 years.”
