Epstein's Former Assistant Tells How Donald Trump 'Regaled' Twisted Tycoon With Creepy 'Tales of His Sexual Exploits' When on Loud Speaker
Donald Trump and Jeffrey Epstein were once close friends.
Dec. 23 2025, Published 12:50 p.m. ET
Donald Trump reportedly reveled in sharing and boasting with Jeffrey Epstein tales of his sexual exploits, RadarOnline.com has learned.
And the disgraced s-- offender seemed to delight in how the president's prowess made his female employees uneasy.
Trump and Epstein's Friendship Exposed
A new report indicated Epstein enjoyed making sure his employees could hear tales of Trump's sexual conquests.
The exact nature of Trump's friendship with Epstein has long been debated, with the controversial president insisting he ditched the financier before any of his s-- trafficking allegations became public.
However, Epstein's former employees painted a different picture, sharing tales of the two swapping stories of their sexual conquests in what was described as an ego-driven game of one-upmanship.
One of Epstein's personal assistants told the New York Times when she worked late and the office had emptied, the businessman would put Trump on a speakerphone to make sure she could hear.
Trump and Epstein's Sophomoric Behavior
The phone conversations often turned juvenile.
"Mr. Trump, she said, seemed to enjoy regaling Mr. Epstein with tales of his sexual exploits," according to the report. "And Mr. Epstein seemed to delight in how uncomfortable it made her to overhear them."
And the calls would often turn graphic and sophomoric
"She remembered one call in the mid-1990s on which the two men discussed how much pubic hair a particular woman had, and whether there was enough for Mr. Epstein to floss his teeth with," the article claimed.
"On another, Mr. Trump told Mr. Epstein about having s-- with another woman on a pool table."
Trump Once Called Epstein a 'Terrific Guy'
A "statue" of Trump and Epstein's friendship was briefly erected in Washington, D.C.
Questions about Trump's relationship with Epstein have haunted the president – especially as he tried repeatedly to shift focus away from their friendship. But a connection between the two has not been denied.
Epstein and Trump were once good friends. The two ran in elite Manhattan social circles from the 80s into the 2000s.
The s-- offender's home in Palm Beach was also a short drive from Trump's Mar-a-Lago club, where he was a frequent guest. A resurfaced video from 1992 shows the two men at the club, laughing and pointing out women on the dance floor.
"I've known Jeff for 15 years. Terrific guy," Trump said in a 2002 interview. "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."
Trump Insists He Was 'Not a Fan' of Epstein
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Trump has admitted to knowing Epstein, but insists their relationship was short-lived.
Despite their apparent closeness, the two eventually had a falling out in 2004 over a Palm Beach property dispute. Earlier this year, Trump claimed he had Epstein booted from Mar-a-Lago after learning his employees were being "stolen" from his spa.
He explained: "People that work in the spa – I have a great spa, one of the best spas in the world at Mar-a-Lago – and people were taken out of the spa, hired by (Epstein). In other words, gone. And other people would come and complain, 'This guy is taking people from the spa.' I didn’t know that."
"And then when I heard about it, I told him. I said, 'Listen, we don't want you taking our people.' Whether it was spa or not spa, I don't want him taking people. And he was fine, then not too long after that, he did it again, and I said, 'out of here,'" the former reality star added about apparently kicking Epstein out of his club.
Trump doubled down on his disdain in a different interview, telling a reporter, "I was not a fan. I had a falling out with him a long time ago."
