What we know about Trump’s relationship with Jeffrey Epstein

Just how close was President Donald Trump to Jeffrey Epstein — and how much did he know about Epstein’s crimes?

The president’s onetime friendship with Jeffrey Epstein — the well-connected financier who was indicted for sex trafficking underage girls and died in prison in 2019 — has long been a matter of public record.

But new emails, obtained from the Epstein estate by Congress and released by House Democrats Wednesday, add more to the story.

In a 2019 email (once Trump was president), Epstein wrote to journalist Michael Wolff, “of course he knew about the girls as he asked ghislaine to stop.”

And back in 2011, Epstein emailed his companion and co-conspirator, Ghislaine Maxwell, to say that “the dog that hasn’t barked is trump,” who, he claimed, “spent hours at my house” with one of his victims — whose name House Democrats redacted.

However, House Republicans subsequently revealed the redacted name was “Virginia” and referred to the late Virginia Giuffre — and Giuffre had previously testified that Trump was not involved in the abuse she suffered.

The emails add to the pile of public signs that Trump was well aware of Epstein’s sexual proclivities, but they are also lacking details or specifics.

Epstein and Trump had socialized together frequently in New York City and Palm Beach from the late 1980s to the early 2000s. In 2002, Trump praised Epstein to a reporter as a “terrific guy” — and curiously added that he “likes beautiful women” on “the younger side.”

In 2003, Epstein received a “birthday book” with messages from many of his influential friends, and in it, there’s a message from Trump, the Wall Street Journal reported.

Inside a drawing of a naked woman’s outline, the message claims Trump and Epstein have “certain things in common.” It concludes: “A pal is a wonderful thing. Happy Birthday — and may every day be another wonderful secret.” (Trump said that the message is fake and filed a lawsuit against the Journal and its owner, Rupert Murdoch, for publishing the story.)

Much of the online right has been obsessed with the Epstein scandal for years, hoping Democrats and celebrities would be implicated in his sex crimes. They’ve been comparatively uninterested in Trump’s well-documented, decade-plus relationship with Epstein.

However, Trump and Epstein’s friendship did reportedly end in 2004 in a bitter falling-out; they were fighting to buy the same Florida oceanside mansion, and it got ugly.

A talented social climber who rapidly attained massive wealth through mysterious means, Epstein became a fixture of New York City and Palm Beach elite circles by the 1990s.

During this period, both Epstein and Trump frequently dined and partied together, at Trump’s Mar-a-Lago club in Florida and Epstein’s mansion in Manhattan. Both frequently hosted or attended parties featuring many models, cheerleaders, beauty pageant contestants, and other attractive young women as guests. They were often photographed together at these events, often with Epstein’s companion Ghislaine Maxwell as well.

In 1992, the New York Times reported that two dozen women went to Mar-a-Lago for a “calendar girl” competition before only two guests: Trump and Epstein. Per flight logs, Trump flew on Epstein’s private jets seven times between 1993 to 1997, though he never went to the private island in the US Virgin Islands that Epstein purchased in 1998.

Two decades later, in tape-recorded interviews with journalist Michael Wolff, Epstein claimed that he “was Donald’s closest friend for 10 years.” Epstein said that he and Trump frequently picked up women together in Atlantic City casinos, that Trump enjoyed seducing his best friends’ wives, and that the first time Trump “slept with” Melania was “on my plane.” (When Wolff released the tapes last year, Trump’s team dismissed them as “false smears.”)

Both Trump and Epstein were accused of sexual misconduct around this time as well — Trump in a 1997 sexual assault lawsuit, and Epstein in a 1997 police report.

At least once, Mar-a-Lago was allegedly a recruiting site for Epstein’s ring. In 2000, 16-year-old Virginia Giuffre was working as a pool attendant at Trump’s club when Maxwell offered her a job as Epstein’s masseuse. Giuffre alleged that, over the ensuing two years, Epstein and Maxwell then groomed her to have sex with wealthy and influential men, including Prince Andrew of the British royal family. Guiffre died by suicide earlier this year.

When a journalist for New York magazine profiled Epstein in 2002, Trump gave that quote that seemed to allude to Epstein’s preference for young women. “I’ve known Jeff for 15 years. Terrific guy,” he said. “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.”

Then, in 2003, came the birthday book. According to the Wall Street Journal, it was assembled by Maxwell, and contained joking and innuendo-laden messages from many of Epstein’s friends.

The entry with Trump’s name contained a drawing of the outline of a naked woman, with the signature “Donald” below her waist, and an odd, typewritten message purporting to be a dialogue between Trump and Epstein. In the dialogue, “Donald” says “We have certain things in common, Jeffrey,” and “Enigmas never age.”

The dialogue concludes with “Donald” saying: “A pal is a wonderful thing. Happy Birthday — and may every day be another wonderful secret.” Per the Journal, the book is currently in the Justice Department’s possession.

Trump claims the book is fake, asserting “these are not my words,” and claiming “I don’t draw pictures.” (There are many articles about Trump’s penchant for doodling, sketching and drawing, containing numerous examples of such.)

Salacious as the birthday book sounds, it does not actually prove any misconduct on Trump’s part: The message is vague. But it fed intense speculation on exactly what Trump was referring to about “things in common” and a “wonderful secret.”

In court proceedings and grand jury questioning, Epstein victims have accused several powerful and influential men of being involved in his sex crimes — but these names have largely been reported, and Trump’s name was not among them. In 2016, an anonymous plaintiff filed a lawsuit claiming Trump and Epstein had raped her, but the circumstances around the lawsuit looked very sketchy, and it was soon dropped.

Trump and Epstein’s happy friendship did not last — because, in 2004, Trump and Epstein both badly wanted to buy the same oceanfront Palm Beach mansion up for auction.

The Washington Post chronicled the bitter falling-out, which involved competing bids, each trashing the other to the trustee managing the auction, and threats of lawsuits. (Trump won the mansion, but sold it a few years later to a Russian billionaire.)

This appears to have been a definitive break, as there’s no evidence that Trump and Epstein socialized again after this point.

Just two weeks after the property auction, the Palm Beach police received a tip that young women had been seen entering and leaving Epstein’s home.

The investigation into Epstein truly kicked off the following year, in 2005, when a 14-year-old girl and her parents went to the Palm Beach police, accusing Epstein of molesting her during a massage. Epstein was charged in Florida in 2006, but the case was resolved in 2008 in what was later derided as a sweetheart plea deal.

After that, Epstein’s victims pressed their case in civil lawsuits. An attorney for the victims, Brad Edwards, has said that, in 2009, he sought information from various Epstein acquaintances. Very few were willing to talk voluntarily, but Trump was — and Edwards said he was “very helpful in the information that he gave.”

In a court filing, Edwards asserted that Trump banned Epstein from Mar-a-Lago “because Epstein sexually assaulted an underage girl at the club.” This was likely the information Trump provided, since Trump has told others this as well. But the story has never been corroborated, and details on when this happened remain elusive. (In a newly released email to journalist Michael Wolff, Epstein disputed that he was pushed out of Mar-a-Lago, claiming that he was “never a member ever.”

Once Trump was president, media reporting revived interest in the Epstein case, and he was arrested on new charges in 2019. He died in prison a month later, in what FBI investigators say was a suicide.

Maxwell, Epstein’s companion, was arrested the following year, in 2020. “I do wish her well,” Trump said then. “I’m not looking for anything bad for her.”

Update, November 12, 2025, 3:35 pm ET: This article was originally published on July 18 and has been updated with new developments.