I Know Truth About Why Epstein and Trump Fell Out: Michael 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.

Visited 1 times, 1 visit(s) today

Related Article

Nvidia’s trillion-dollar run puts pressure on the bulls

BEIJING, CHINA – MAY 14: Nvidia CEO Jensen Huang (C) gestures as he prepares to depart following a welcome ceremony at the Great Hall of the People on May 14, 2026 in Beijing, China. President Trump is meeting with President Xi Jinping in Beijing to address the Iran conflict, trade imbalances, and the Taiwan situation

Permutations in Europe: What’s still at stake in final weeks of season?

There’s still plenty to play for across Europe as we head into the final matches of the club season. Here are all the title races, Champions League fights, and relegation battles left to be decided in the top leagues this month. This story will be updated until the end of the campaign. 👉 Jump to:EPL

Brewing a Better Half-Gallon Batch

Today I finally ran an experiment I’ve wanted to try for a long time. If you’re a professional barista—or you run a busy café—this may save you some time. Most coffee shops use 1–1.5 gallon batch brewers (Bunn, Curtis, Fetco, etc.). When I opened Short Sleeves Coffee, I intentionally avoided brewing full 1-gallon batches. I

5 Frozen Breakfasts Chefs Say Keep You Full All Morning

Chef-approved frozen breakfasts with more protein and better ingredients. Eating a healthy breakfast every morning is a great way to start the day, but most people don’t have time to cook. Whether you’re rushing out the door in the morning for work, taking the kids to school or both, there’s usually not much time in

CA scales back plan to ban student use of cell phones

By Carolyn Jones, CalMatters This story was originally published by CalMatters. Sign up for their newsletters. Until last month, California was poised to join nearly a dozen other states that ban cell phones in K-12 schools. But under pressure from school boards and administrators, lawmakers scaled back a bill that would have required such a

BulkQuant Launches AI Trading Bot for Crypto, Forex, and Stock Markets

BulkQuant Launches AI Trading Bot for Crypto, Forex, and Stock Markets

London, United Kingdom, May 15, 2026 (GLOBE NEWSWIRE) — BulkQuant has officially launched its AI trading bot platform designed for crypto, forex, and stock market traders seeking a simpler way to automate trading strategies across multiple financial markets. The platform combines AI-powered quantitative analysis, automated trade execution, portfolio monitoring, and adaptive risk management into a

IMF lauds resilient Hong Kong economy but warns of risks linked to Middle East war

IMF lauds resilient Hong Kong economy but warns of risks linked to Middle East war

The International Monetary Fund (IMF) has lauded the resilience of Hong Kong’s economy, noting a sustained recovery despite economic activity having yet to return to pre-Covid levels, while warning of downside risks stemming from escalating geopolitical tensions. It also urged Hong Kong to pursue medium-term financial reforms, including the introduction of a goods and services

Smithsonian Presidents Exhibit Reopens With Low-Key Trump Impeachment Mention

For the past year, the Smithsonian Institution has found itself in the awkward position of telling the nation’s story while being supported in part by a government that wants to narrow how that story is told. In December, the White House threatened to revoke funding to the institution if it did not hand over a

Marvel’s Daredevil Follow-up Is Already Dominating on Streaming

A follow-up to Daredevil: Born Again Season 2 on Disney+ has become a massive streaming success within days of its launch. The Punisher: One Last Kill has quickly climbed to the top of multiple charts, beating out other titles on the platform. The MCU television special follows the gun-toting vigilante, who finds himself targeted by

Is Now a Bad Time to Invest?

The market has been on a roll lately, with the S&P 500 (SNPINDEX: ^GSPC) setting new highs throughout May. If you think you missed your opportunity when the market bottomed in late March, don’t fret. The market hitting new all-time highs is not particularly rare and should not change your investment strategy. And if you

6 bids for Hong Kong land sale signal renewed confidence despite market caution

6 bids for Hong Kong land sale signal renewed confidence despite market caution

The Hong Kong government’s first land sale in the current financial year has drawn six bids, according to the Development Bureau, including those from the city’s largest developers, suggesting a more confident outlook for the residential property market. At the close of tender for Tung Chung Town Lot No 54 at Area 106A on Friday

Each Premier League team reranked: Man City rise; Chelsea, Liverpool collapse

Ryan O’Hanlon Close Ryan O’Hanlon ESPN.com writer Ryan O’Hanlon is a staff writer for ESPN.com. He’s also the author of “Net Gains: Inside the Beautiful Game’s Analytics Revolution.”  and  Bill Connelly Close Bill Connelly ESPN Staff Writer Bill Connelly is a writer for ESPN. He covers college football, soccer and tennis. He has been at

Trump departs China after two-day summit

Trump departs China after two-day summit

IE 11 is not supported. For an optimal experience visit our site on another browser. Trump Wraps China Summit With Xi Jinping: What Are the Results? 05:41 Xi gives Trump rare tour of secret garden at heart of Chinese government 01:04 Now Playing Trump departs China after two-day summit 01:01 UP NEXT Special Report: Trump

Carol Chow was facing a bankruptcy petition by five people over unspecified debts at the time of her death. Photo: Dickson Lee

Embattled Hong Kong developer sued for HK$130 million, days after founder’s death

A Hong Kong property developer has been sued for HK$130 million (US$16.6 million) over allegedly breaching guarantor obligations in two bond subscription agreements, becoming the latest lawsuit to implicate the embattled company and following its founder’s sudden death earlier this week. Lofter Group, known for its urban renewal projects across the city’s core districts, and

Trump’s China visit left chip export issue unresolved

This report is from this week’s The Tech Download newsletter. Like what you see? You can subscribe here. One look at the roster of U.S. execs that cozied up to U.S. President Donald Trump on the 20+ hours flight from Alaska to China on Wednesday and you get a sense of the American delegation’s key focus

Why the Cerebras IPO matters for the AI race with China

Why the Cerebras IPO matters for the AI race with China

Cerebras, an AI chipmaker, saw its shares nearly double on Nasdaq, closing up 70% with a $95B market cap. Cerebras’s powerful chips are key in the US-China AI tech race. Chris Buskirk, co-founder and chief investment officer of 1789 Capital, a key Cerebras investor, says the company’s IPO is geopolitically significant. On Thursday, shares of

Fitbit Air vs Whoop Strap Comparison: Price, Features and AI

The Google Fitbit Air is very much the talk of the fitness tracking town right now, not only because it’s the first new Fitbit device that we’ve had in years, but it’s also one of the first big brands to go head-to-head with the established Whoop Strap (if you don’t count the Polar Loop and

0
Would love your thoughts, please comment.x
()
x