With the release of the new Epstein files, the scrutiny over the relations that President Donald Trump shared with the disgraced financier has been renewed. While the official White House statement has mentioned that Trump had fallen out with Epstein because of the latter’s abuse of young girls, the President’s biographer, Michael Wolff, mentioned a completely different reason behind the two discontinuing their friendship.
Talking to co-host Joanna Coles on the latest episode of their podcast Inside Trump’s Head, Wolff said that the real reason that the two fell out was because Trump went behind Epstein’s back and made a successful bid on a property in Palm Beach that was worth around tens of millions of dollars.
Explaining the same, Wolff said, “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. If they get screwed in a real estate deal, that breaks up any rich guy relationship.”
Inside Trump’s head podcast seems to be in front of all of this with Michael Wolff. pic.twitter.com/nElgZeYZFn
— MAGA Cult Slayer🦅🇺🇸 (@MAGACult2) January 1, 2026
Trump and Epstein became friends in the late 1980s. Both were prominent figures in Manhattan and Palm Beach social scenes. One of the common points of the two bonding were models, as they represented status, as Wolff said. He then added, “I have never known anyone who is so devoted to this idea of… the personal playboy ideal. I think they both venerated [Playboy magazine founder] Hugh Hefner.”
As the friendship between the two kept getting stronger, Trump’s financial condition took a dive as his Atlantic City properties were going almost bankrupt. Epstein was very likely doing better than Trump in terms of finances and believed that he had the upper hand in their relationship.
Wolff further explained that the private jets that Trump took to go between Manhattan and Palm Beach were owned by Epstein. Moreover, Trump had turned his Mar-a-Lago into a members-only club by then, which he had originally bought as a property of residence. Wolff added, “He would say it’s not a house. He has to take in boarders because he has no money.”
By the beginning of the 2000s, there were already profiles on Epstein that were running in Vanity Fair and New York magazine. However, Trump had not yet fallen out with him yet and in a 2002 interview with New York Magazine, he said, “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.”
Michael Wolff on Trump/Epstein Scandal: “The fear is that Ghislaine Maxwell can tie Trump to the details of what Trump and Epstein called the Committee. The Committee consisted of Trump and Epstein in their efforts to get girls for Prince Andrew.”pic.twitter.com/cAJ865XaDY
— The Intellectualist (@highbrow_nobrow) December 25, 2025
However, things started getting sour when, in 2004, Trump reportedly went behind Epstein’s back and outbid him on a $36 million property in Palm Beach. Epstein had originally shown Trump the property to discuss some ideas about moving the swimming pool. However, Trump then went ahead on his own and bid $40 million on the same property, which angered Epstein and gradually led to the end of their friendship. However, Wolff also mentioned that even after the friendship between them ended, Epstein remained obsessed with Trump.
Interestingly, Trump’s take on the whole thing is entirely different, as whenever he has been asked about why the friendship between him and Epstein ended, he has 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.”
Wolff’s claims about the reason between the two falling out were violently dismissed by White House communications director Steven Cheung as he said in a statement to the Daily Beast, “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.”
While Trump and his administration have been doing their best to hide the President’s ties with Epstein, with the emergence of new evidence and people speaking up, that is becoming a really difficult task.
