Inside the Long Friendship Between
Trump and Epstein
For nearly 15 years, the two men socialized together in
Manhattan and Palm Beach, Fla., before a falling out that preceded Mr.
Epstein’s first arrest.
By Alan Feuer and Matthew
Goldstein
- July 19, 2025
In the swirl of money
and sun-tanned women that was their Palm Beach-and-Manhattan set, Donald J.
Trump and Jeffrey Epstein spent nearly 15 years mingling side-by-side as public
friends.
There were lavish
dinners with boldface names at Mr. Epstein’s mansion on the Upper East Side and
raucous parties with cheerleaders and models at Mr. Trump’s private club and
residence at Mar-a-Lago. In between, there were trips back and forth from Florida
to New York on one of Mr. Epstein’s private jets.
But behind the tabloid
glamour, questions have lingered about what Mr. Trump’s long association with
Mr. Epstein says about his judgment and character, especially as his allies
have stoked sinister claims about Mr. Epstein’s connections to Democrats. After
their relationship ruptured, the disgraced financier ended up behind bars not
just once, but two times, after being accused of engaging in sex with teenage
girls.
One of the young women who later said
Mr. Epstein groomed and abused her was recruited into his world while working
as a spa attendant at Mar-a-Lago. Another accuser recalled being eyed by Mr. Trump during a brief
encounter in Mr. Epstein’s office, and claimed that Mr. Epstein had told Mr.
Trump at the time that “she’s not for you.”
Another woman has said
that Mr. Trump groped her when Mr. Epstein brought her
to Trump Tower in Manhattan to meet him. This week, The Wall Street Journal reported
that Mr. Trump gave Mr. Epstein a note for his 50th birthday in 2003 that
included a sketch of a naked woman and a cryptic reference to a “secret” the
two men shared. Mr. Trump has denied writing the message and filed a libel
lawsuit on Friday challenging the story. The New York Times has not verified
the Journal report.
Mr. Trump has never been
accused of wrongdoing in connection with the Epstein case, and has said he had
“no idea” that Mr. Epstein was abusing young women. In response to a request
for comment about the president’s history with Mr. Epstein, Karoline Leavitt,
the White House press secretary, said that Mr. Trump had barred Mr. Epstein
from his Mar-a-Lago club “for being a creep.”
“These stories are tired
and pathetic attempts to distract from all the success of President Trump’s
administration,” she said in a statement.
Mr. Trump and Mr. Epstein largely went
separate ways after a falling-out around 2004, taking drastically different
paths — one toward jail and suicide, the other toward further celebrity and the
White House.
As criticism of the handling of Mr.
Epstein’s case mounted over the years, some of Mr. Trump’s staunchest allies
promoted theories that the government had covered up the extent of his network
to protect what they have described as a cabal of powerful men and celebrities,
largely Democrats.
Now, that story has
entangled Mr. Trump himself in what amounts to one of the biggest controversies
in his second White House stint. The conflict has come primarily from his own
appointees, who, after months of promoting interest in the files, abruptly changed
course and said that there was no secret Epstein client list and backed the
official finding that Mr. Epstein had killed himself.
Still, under mounting
pressure from his own supporters to release the government’s files on Mr.
Epstein, the president this week ordered the Justice Department to seek the
unsealing of grand jury testimony in the criminal case brought against Mr.
Epstein in 2019 and one year later against his longtime partner, Ghislaine
Maxwell, who is serving a 20-year sentence on a sex-trafficking conviction. She
has asked the Supreme Court to consider her appeal.
Even if they are
released, the transcripts are unlikely to shed much light on the relationship
between the two men, which did not figure prominently in either criminal case.
What seemed to draw them together, according to those who knew them at the
time, was a common interest in hitting on — and competing for — attractive
young women at parties, nightclubs and other private events.
Palm Beach Neighbors
Mr. Trump and Mr. Epstein appear to
have met around 1990, when Mr. Epstein bought a property two miles north of
Mar-a-Lago and set about staking a claim in Palm Beach’s moneyed, salt-air
social scene. Mr. Trump, who had purchased Mar-a-Lago five years earlier, had
already established his own brash presence in the seaside enclave as a playboy
with a taste for gold-leaf finery.
The two had much in common. Both were
outer-borough New Yorkers who had succeeded in Manhattan. Both were energetic
self-promoters. And both had reputations as showy men-about-town.
Mr. Trump and Mr. Epstein at
Mar-a-Lago in 1997.Credit...Davidoff Studios
Photography/Archive Photos, via Getty Images
In 1992, an NBC News
camera captured the pair at
a Mar-a-Lago party that featured cheerleaders from the Buffalo Bills, who were
in town that weekend for a game against the Miami Dolphins. At one point in the
footage, Mr. Trump can be seen dancing amid a crowd of young
women. Later, he appears to be pointing at other women while
whispering something in Mr. Epstein’s ear, causing him to double over with
laughter.
Months later, when Mr.
Trump hosted a party at Mar-a-Lago for young women in a so-called calendar girl
competition, Mr. Epstein was the only other guest, according to George
Houraney, a Florida-based businessman who arranged the event. Mr.
Houraney recalled being surprised that Mr. Epstein was the
only other person on the guest list.
“I said, ‘Donald, this is supposed to
be a party with V.I.P.s,” Mr. Houraney told The New York Times in 2019. “You’re
telling me it’s you and Epstein?’”
Mr. Houraney’s
then-girlfriend and business partner, Jill Harth, later accused Mr. Trump of
sexual misconduct on the night of the party. In a lawsuit, Ms. Harth said that Mr. Trump took her into a
bedroom and forcibly kissed and fondled
her, and restrained her from leaving. She also said that a
22-year-old contestant told her that Mr. Trump later that night crawled into
her bed uninvited.
Ms. Harth dropped her
suit in 1997 after a related case filed by Mr. Houraney was settled by Mr.
Trump, who has denied her allegations.
Mr. Trump and Mr. Epstein were spotted
again at a 1997 Victoria’s Secret “Angels” party in Manhattan. The lingerie
company was run by Leslie H. Wexner, a billionaire businessman who handed Mr.
Epstein sweeping power over his finances, philanthropy and
private life within years of meeting him.
Court records show that Mr. Trump was
among those who got rides on Mr. Epstein’s private jet. Over four years in the
1990s, he flew on Mr. Epstein’s Boeing 727 at least seven times, largely making
jaunts between Palm Beach and a private airport in Teterboro, N.J., just
outside New York.
“I’ve known Jeff for 15
years. Terrific guy,” Mr. Trump told New York magazine in 2002. “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.”
An Encounter at Mar-a-Lago
In 2000, court records
show, Ms. Maxwell, a British socialite who had long been tied to Mr. Epstein,
struck up a conversation with a 17-year-old girl outside a locker room at
Mar-a-Lago.
Her name was Virginia
Giuffre, and she was a spa attendant at the club, having gotten the job through
her father, who worked there as a maintenance man. According to Ms. Giuffre,
Ms. Maxwell offered her a job on the spot as a masseuse for Mr. Epstein after
seeing that she was reading a book about massage, telling her that she did not
need to have any experience.
She said that when she
was brought to Mr. Epstein’s Palm Beach home, she found him lying naked on a
table. Ms. Maxwell, she claimed, instructed her on how to massage him.
“They seemed like nice
people,” she later testified, “so I trusted them.”
But over the next two years or so, Ms.
Giuffre claimed that she was forced by Mr. Epstein and Ms. Maxwell to have sex
with a series of famous men, including Prince Andrew, a member of the British
royal family. Prince Andrew has denied the accusations and declined to help federal prosecutors in their
investigation of Mr. Epstein.
Ms. Giuffre, who died by suicide in April, always maintained that
she was trafficked to the prince and other men, once telling the BBC that she
had been “passed around like a platter of fruit” to Mr. Epstein’s powerful
associates.
Some women who were in
Mr. Epstein’s orbit have said they encountered Mr. Trump during this period.
One woman, Maria Farmer,
who has said she was victimized by Mr. Epstein and Ms. Maxwell, described an encounter with Mr. Trump in 1995 at
an office that Mr. Epstein once kept in New York City.
An art student who had
moved to New York City to pursue a career as a painter, Ms. Farmer recalled in
a 2019 interview that when she was introduced to Mr. Trump, he eyed her,
prompting Mr. Epstein to warn him, “She’s not for you.”
Ms. Farmer’s mother, Janice Swain,
said her daughter had described the interaction with Mr. Trump around the time
it occurred.
Stacey Williams, a
former Sports Illustrated swimsuit model, has said she was groped by Mr. Trump
when she was introduced to him by Mr. Epstein, whom she was dating at the time.
It was 1993, she said,
and she was on a walk with Mr. Epstein on Fifth Avenue in Manhattan, when he
suggested that they pop into Trump Tower to say hello to Mr. Trump. Ms.
Williams thought nothing of it at the time because, as she later put it,
“Jeffrey talked about Trump all the time.”
After Mr. Trump greeted
them in a waiting area outside his office, Ms. Williams said, he pulled her toward him, touching her breasts, waist
and buttocks as though he was “an octopus.”
She said she later
wondered whether she had been part of a challenge or wager between the two men.
“I definitely felt like I was a piece of meat delivered to that office as some
sort of game,” she recalled to The Times last year. At the time, Mr. Trump’s
presidential campaign denied that the incident had occurred, calling the
allegations “unequivocally false” and politically motivated.
In an interview Friday, Ms. Williams
said she was upset to hear Mr. Trump referring to some of the Epstein story as
a “hoax” and “boring” news. “I mean, it’s absurd,” she said of him speaking
dismissively of the case.
The Break
Eventually, in late
2004, Mr. Trump and Mr. Epstein ended up squaring off —
this time, over a piece of real estate. It was the Maison de l’Amitié, a French
Regency-style manse that sat along the ocean in Palm Beach.
The two hypercompetitive
men each had their lawyers bid on the property. Ultimately, Mr. Trump came out
ahead, purchasing it for $41.35 million.
There is little public
record of the two men interacting after that.
Mr. Trump later told
associates he had another reason for breaking from Mr. Epstein around that
time: His longtime friend, he has said, acted inappropriately to the daughter
of a member of Mar-a-Lago, and Mr. Trump felt compelled to bar him from the
club. Brad Edwards, a lawyer who has represented many of Mr. Epstein’s victims,
said Mr. Trump told him a similar story in 2009.
Not long after the standoff over the
beachfront mansion, the Palm Beach police received a tip that young women had
been seen going in and out of Mr. Epstein’s home.
Four months later, there
was a more substantial complaint from a woman who claimed that her 14-year-old
stepdaughter had been paid $300 by Mr. Epstein to give him a massage while she
was undressed. That led to a sprawling undercover investigation that identified
at least a dozen potential victims.
Mr. Epstein hired a team
of top lawyers to defend him — among them, Alan M. Dershowitz, a Harvard law
professor who would later represent Mr. Trump, and Ken Starr, the former
independent counsel who investigated President Bill Clinton’s affair with Monica
Lewinsky.
The two men helped
negotiate a lenient plea deal with R. Alexander Acosta, who was then the U.S.
attorney for the Southern District of Florida. Under the deal, Mr. Epstein
pleaded guilty in 2008 to state charges of soliciting prostitution. In
exchange, he was granted immunity from federal charges, as were all of his
potential co-conspirators. He also had to register as a sex offender.
In the end, Mr. Epstein
wound up serving almost 13 months in jail before he was released.
For his part, Mr. Trump
largely steered clear of the controversy. But in February 2015, as he was
gearing up for what would end up being a hard-fought campaign against Hillary
Clinton, he sought to connect Mr. Epstein to her husband, the former president.
Mr. Clinton has “got a lot of problems
coming up, in my opinion, with the famous island with Jeffrey Epstein,” Mr.
Trump told the Fox News host Sean Hannity during an appearance at the
Conservative Political Action Conference, referring to Mr. Epstein’s private island where he resided and allegedly
trafficked underage girls. “A lot of problems.”
Mr. Clinton has denied
visiting the island or having any knowledge of Mr. Epstein’s criminal behavior,
and has said he wishes he had never met him.
‘I Wasn’t a Fan’
In July 2019, Mr.
Epstein was arrested again. Prosecutors from the public corruption unit of the
U.S. attorney’s office in Manhattan charged him with sex trafficking and a
conspiracy to traffic minors for sex.
Mr. Trump, then in his
third year in the White House, immediately sought to distance himself from his
old friend.
“I knew him like everybody in Palm
Beach knew him,” Mr. Trump told reporters after the charges were revealed. “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 in 15
years. I wasn’t a fan.”
The new charges brought
renewed scrutiny to the original plea deal. Days after Mr. Epstein’s arrest,
Mr. Acosta, who had become Mr. Trump’s labor secretary, announced he would resign amid criticism of his
handling of the case.
Speaking to reporters
about Mr. Acosta’s decision, Mr. Trump reiterated that
he had broken off his ties with Mr. Epstein “many, many years ago.” He added:
“It shows you one thing: that I have good taste.”
When asked if he had any
suspicions that Mr. Epstein was molesting young women, Mr. Trump replied, “No,
I had no idea.”
The next month, after
Mr. Epstein was suddenly found dead in his jail cell in Manhattan in what was
later ruled a suicide, Mr. Trump weighed in again, reviving what was by then a
years-old effort from his first campaign. He shared a social media post that attempted to link
the death to Mr. Clinton.
Days later, when pressed about his
unfounded claims of Mr. Clinton’s involvement, Mr. Trump did not let up,
calling for a full investigation, even though he offered no facts to support
his allegations.
“Epstein had an island
that was not a good place, as I understand it,” he said. “And I was never
there. So you have to ask: Did Bill Clinton go to the island?”
When Mr. Trump was asked
about the arrest of Ms. Maxwell in the summer of 2020 on charges that included
the enticement and trafficking of children, his answer left some of his own
allies confused.
“I wish her well, whatever it is,” Mr.
Trump said.
In recent weeks,
right-wing influencers and Mr. Trump’s rank-and-file supporters expressed
outrage over his administration’s conclusion that there were no revelations to
share about the case — not least because some of the president’s top law
enforcement officials, including Attorney General Pam Bondi and Kash Patel, the
F.B.I. director, had promised to reveal more information about Mr. Epstein’s
crimes.
Mr. Trump sought to quiet the demands, calling the Epstein
scandal a “hoax” made up by his Democratic adversaries. He also described it as
a subject unworthy of further scrutiny.
“Are you still talking
about Jeffrey Epstein?” Mr. Trump asked reporters with exasperation at a
cabinet meeting on July 8. “This guy’s been talked about for years.”
