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I Know Truth About Why Epstein and Trump Fell Out: Wolff

January 2, 2026
in News, Politics
I Know Truth About Why Epstein and Trump Fell Out: Wolff

President Donald Trump’s 15-year friendship with Jeffrey Epstein ended over a real estate deal, not the late sex offender’s abuse of young girls, according to biographer Michael Wolff.

The White House’s official line is that the two men had a falling out in the early 2000s after Trump kicked Epstein out of his Mar-a-Lago club in Palm Beach, Florida, for “being a creep.”

Jeffery Epstein and Donald Trump
Photo Illustration by Victoria Sunday/The Daily Beast/Getty Images

But according to Wolff, the rift developed after Trump went behind Epstein’s back and successfully bid on a property in Palm Beach worth tens of millions of dollars, as he told co-host Joanna Coles on the latest episode of their podcast Inside Trump’s Head.

“These guys… they’re devoted to their private plans, but the thing that really makes them crazy is real estate—their quest for real estate,” Wolff said. “If they get screwed in a real estate deal, that breaks up any rich guy relationship.”

Donald Trump with his then-girlfriend (and now wife), Melania Knauss, Jeffrey Epstein, and Ghislaine Maxwell.
Donald Trump with his then-girlfriend (and now wife), Melania Knauss, Jeffrey Epstein, and Ghislaine Maxwell. Davidoff Studios/Getty Images

Epstein and Trump were close friends for years, beginning in the late 1980s.

They were both fixtures of the Manhattan and Palm Beach social scenes, forming a close relationship as they bonded over their obsession with models, who represented not just sex, but status, according to Wolff.

“I have never known anyone who is so devoted to this idea of… the personal playboy ideal,” Wolff said. “I think they both venerated [Playboy magazine founder] Hugh Hefner.”

By the late 1990s, Trump had separated from his second wife, Marla Maples, and had recently met model Melania Knauss, whom he would marry in 2005.

At the time, Trump’s Atlantic City properties were going bankrupt and he was in a financially precarious position, despite having his name on buildings around Manhattan and projecting an aura of success, according to Wolff.

Donald Trump and Marla Maples at their wedding.
Epstein attended Trump’s 1993 wedding to Marla Maples. Ron Galella Collection via Getty

Epstein probably had more money than Trump, who by then had become a tabloid joke, and the financier believed he had the upper hand in their relationship, he added.

Epstein was the one who provided the private plane that shuttled them between Manhattan and Palm Beach, Wolff explained, and he would make fun of Trump’s residence at Mar-a-Lago, which the president originally bought as a private residence before turning it into a members-only club.

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)
Trump and Epstein at a Victoria’s Secret event in 1997. Thomas Concordia/Thomas Concordia/Getty Images

“He would say it’s not a house. He has to take in boarders because he has no money,” Wolff said.

Their friendship was still going strong in the early 2000s, when lengthy magazine profiles about Epstein ran in Vanity Fair and New York magazine.

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 on February 22, 1997. (Photo by Davidoff Studios/Getty Images)
Trump and Epstein’s relationship has become a global source of intense conversation and speculation. Davidoff Studios Photography/Getty Images

“I’ve known Jeff for 15 years. Terrific guy,” Trump told the reporter from 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.”

Two years later, in 2004, Epstein believed he was the top bidder for a $36 million property in Palm Beach. He took Trump to see the property to offer some advice on how to move the swimming pool, Wolff said.

Donald Trump and Jeffrey Epstein at a Mar-a-Lago party in 1992.
Donald Trump and Jeffrey Epstein at a Mar-a-Lago party in 1992. screen grab

Trump then went behind Epstein’s back and bid $40 million for the property.

“Epstein is furious about this,” Wolff said.

NEW YORK, NY - MAY 18: Jeffrey Epstein attends Launch of RADAR MAGAZINE at Hotel QT on May 18, 2005. (Photo by Neil Rasmus/Patrick McMullan via Getty Images)
Epstein attends a magazine launch party in 2005. Patrick McMullan/Patrick McMullan via Getty Image

When asked earlier this year why their relationship ended, Trump said, “Because he did something that was inappropriate. He hired help. I said, ‘Don’t ever do that again.’ He did it again, and I threw him out of the place, persona non grata.”

In a statement to the Daily Beast, White House communications director Steven Cheung provided his boilerplate statement, “Michael Wolff is a lying sack of s–t and has been proven to be a fraud. He routinely fabricates stories originating from his sick and warped imagination, only possible because he has a severe and debilitating case of Trump Derangement Syndrome that has rotted his peanut-sized brain.”

According to Wolff, Epstein remained obsessed with Trump even after their falling out, and the disgraced financier remains one of the few topics that makes the president nervous.

In this handout, the mug shot of Jeffrey Epstein, 2019.
Jeffrey Epstein died in 2019 while awaiting federal sex trafficking charges. Kypros/Getty Images

Trump has never been formally accused of any wrongdoing despite his long friendship with Epstein, who pleaded guilty in 2008 to procuring a child for prostitution.

The disgraced financier died in a Manhattan jail cell in 2019 while awaiting trial on sex trafficking charges.

Find and subscribe to Inside Trump’s Head with Michael Wolff and Joanna Coles on YouTube and wherever you get your podcasts. New episodes of incomparable insight into the psyche of the world’s most talked-about man drop every Tuesday, Thursday, and Saturday evening on YouTube and Wednesday and Friday mornings on other podcast platforms.

The post I Know Truth About Why Epstein and Trump Fell Out: Wolff appeared first on The Daily Beast.

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