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Trump biographer shares reason ‘rich guy relationship’ with Trump and Epstein broke down

January 2, 2026
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Trump biographer shares reason ‘rich guy relationship’ with Trump and Epstein broke down

The “rich guy relationship” between Donald Trump and Jeffrey Epstein began breaking down for one reason, according to a presidential biographer.

Michael Wolff, who documented Trump’s first term in the White House, suggested the rift between Epstein and Trump developed because of a property deal in Palm Beach. Wolff, speaking on an episode of the Inside Trump’s Head podcast, explained the close friendship started to end because of the real estate opportunity.

He 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.” Epstein and Trump had been friends since in the late 1980s, according to The Daily Beast.

But the Palm Beach deal, which saw Trump bid on a property behind Epstein’s back in 2004, seemed to sour the relationship. Epstein had bid $36million for the house, even taking Trump to the property and asking for advice on how to renovate.

Trump would go on to bid $40million for the property, behind Epstein’s back. Wolff continued, “Epstein is furious about this.” Wolff would go on to say the pair were “best friends” and that Trump “lived the life of a sleazeball” during his time with Epstein.

Trump would claim the relationship with Epstein ended shortly after an incident at Mar-a-Lago. The president said earlier this year, “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.”

The incident in question was reported on December 31, with a report released by the Wall Street Journal claiming Trump’s break with Epstein came after an 18-year-old Mar-a-Lago beautician complained that Epstein pressured her for sex after being sent to his residence.

This incident prompted Trump to ban Epstein from the resort. However, the Journal reports that Maples, who was married to Trump from 1993 to 1999, harbored early and prescient skepticism about Epstein—a concern shared with Mar-a-Lago staff members.

Maples also communicated these concerns directly to her husband. Former club employees reported that Maples shared her reservations with Timothy McDaniel, a Trump family bodyguard who oversaw security at their Florida properties.

“Maples told Trump that she was uneasy about Epstein’s presence and that she didn’t want to spend time with him—and didn’t want Trump to either, according to former employees and people close to Maples.”

The post Trump biographer shares reason ‘rich guy relationship’ with Trump and Epstein broke down appeared first on Raw Story.

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