PoliticsDonald Trump and Jeffrey Epstein's Friendship 'Breakup' Occurred After POTUS 'Screwed' Late Pedophile in Real Estate Deal, Claims Michael Wolff

Donald Trump's former friendship with Jeffrey Epstein continues to haunt the president.
Jan. 2 2026, Published 7:43 p.m. ET
Donald Trump's highly-publicized falling out with Jeffrey Epstein may have had less to do with morals and more to do with money, according to journalist Michael Wolff.
During the latest episode of his "Inside Trump’s Head" podcast, Wolff told co-host Joanna Coles that the friendship between the former president and Epstein imploded after Trump allegedly undercut the late pedophile in a high-stakes Palm Beach real estate deal worth tens of millions of dollars.
"These guys… the thing that really makes them crazy is real estate — their quest for real estate," Wolff explained. "If they get screwed in a real estate deal, that breaks up any rich guy relationship."
Donald Trump and Jeffrey Epstein Admired Hugh Hefner, Michael Wolff Claims

Donald Trump and Jeffrey Epstein's friendship ended because of a real estate deal, Michael Wolff claimed.
Trump and Epstein were close for years beginning in the late 1980s, frequently appearing together in Manhattan and Palm Beach social circles. According to Wolff, the two men bonded over wealth, status and their shared fixation on models — whom Wolff suggested represented power as much as intercourse.
"I have never known anyone who is so devoted to this idea of… the personal playboy ideal," Wolff said, adding that both men admired Playboy founder Hugh Hefner.
By the late 1990s, Trump's personal and financial life had become increasingly complicated. He had separated from his second wife, Marla Maples, and had recently met Melania Trump (née Knauss), whom he would later marry in 2005.

Donald Trump and Jeffrey Epstein were friends until the early 2000s.
At the same time, Trump’s Atlantic City casinos were failing, and Wolff claimed the real estate mogul was in a more precarious financial position than he portrayed publicly.
Epstein, Wolff alleged, likely had more money than Trump at that point and believed he held the upper hand in their relationship.
Epstein often provided his private jet for travel between New York and Florida and would even mock Trump's Mar-a-Lago estate, which Trump initially purchased as a private residence before converting it into a members-only club.
Donald Trump Allegedly Went Behind Jeffrey Epstein's Back in a Real Estate Deal

Donald Trump claimed he stopped being friends with Jeffrey Epstein because he did something 'inappropriate.'
"He would say it’s not a house. He has to take in boarders because he has no money," Wolff recalled Epstein allegedly saying.
Despite the tension, their friendship appeared intact in the early 2000s.
Trump publicly praised Epstein in a 2002 interview with New York magazine, declaring in an interview, "I’ve known Jeff for 15 years. Terrific guy. 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."
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According to Wolff, the relationship finally took a turn for the worse in 2004, when Epstein believed he was the top bidder for a $36 million waterfront property in Palm Beach. Wolff claimed Epstein even invited Trump to tour the property for advice on relocating the swimming pool.
Trump allegedly went behind Epstein’s back and submitted a $40 million bid for the estate.
"Epstein is furious about this," Wolff noted.

Jeffrey Epstein died by suicide in prison in August 2019.
Trump previously offered a different explanation for their falling out.
When asked last year why the 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 response to Wolff's claims, White House communications director Steven Cheung issued a scathing statement to The Daily Beast, calling Wolff "a lying sack of s---" and accusing him of fabricating stories fueled by what he described as "Trump Derangement Syndrome."
Wolff, however, doubled down on his theory that Epstein remained fixated on Trump long after their friendship collapsed and claimed the deceased criminal is one of the few names to still visibly rattle the former president.
Trump has never been formally accused of wrongdoing related to Epstein, who pleaded guilty in 2008 to procuring a minor for prostitution. Epstein died in a Manhattan jail cell in 2019 while awaiting trial on federal s-- trafficking charges.


