Epstein and Trump — Love Interrupted (Part One)

The long and illustrious friendship between two narcissistic and (alleged) pedophiles

Part One of Three

“I don’t know about Epstein so much as I do the others. Certainly, about the way he died. It’d be interesting to find out what happened there, because that was a weird situation and the cameras didn’t happen to be working, etc., etc. But yeah, I’d go a long way toward that one.” - Donald Trump, answering Rachel Duffy during June 2, 2024 interview on Fox & Friends

“The moral compass just does not exist…”

Sometime around 1988 or 1989 – nobody seems to know exactly when or where – Donald J. Trump met one Jeffrey Epstein, an American financier who liked to surround himself with celebrities and politicians, including Michael Jackson, Kevin Spacey, Bill Clinton, and Prince Andrew. They were neighbors in Palm Beach, Florida (Trump purchased his estate, Mar-a-Lago, in 1985, and Epstein purchased a nearby property, about two miles north of Trump’s, in 1990). The two men saw each other frequently, running in the same Palm Beach social circles and attending parties at each other’s respective properties after meeting, through the 1990s, and into the early 2000s. In a now rather infamous video from 1992, Trump and Epstein can be seen partying down at Mar-a-Lago with various NFL cheerleaders. For some strange reason, Trump had invited NBC to come to his property and film this party he was throwing for himself. The video shows Trump at one point leaning over to Epstein and whispering something that made Epstein laugh. Analysis in 2019 revealed that Trump appears to tell Epstein, “Look at her, back there…she’s hot!”

The two men shared common interests in wealth, status, and the pursuit of women. According to Jack O’Donnell, a former executive at Trump Plaza and Casino, Epstein was perceived to be Trump’s “best friend,” by those who observed the two together.

“In my mind, [Epstein] was his best friend, you know, [throughout] the time I was there for four years.” - Jack O’Connell, recounting his observations of Epstein and Trump to CNN reporter Erin Burnett on the July 16th, 2025, episode of Erin Burnett Outfront

According to O’Donnell, Epstein and Trump were often seen visiting the casino floor together, and he recalled one particular incident where he reprimanded both men for bringing in several girls who were clearly under the New Jersey legal gambling age of 21.

“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.” - Donald Trump, when asked about Jeffrey Epstein’s social life during a 2002 New York Magazine interview

“The moral compass just does not exist.” - Jeffrey Epstein, speaking about Trump

"He's a horrible human being..."

Trump and Epstein were of one mind when it came to partying, as evidenced at a 1993 party Trump hosted at Mar-a-Lago that included approximately 28 young girls who were contestants for that year’s “American Dream Calendar Girls” competition…with Epstein as the only other male guest. Some reports have described the girls as ranging in age between 16 and 20 and the event organizer, George Houraney, as being surprised and a bit shocked that Trump and Epstein were to be the only male guests. He recalled questioning Trump, saying, “Donald, this is supposed to be a party with V.I.P.s You’re telling me it’s you and Epstein?” The “American Dream Calendar Girls” competition was scheduled to take place in November of that year at Trump’s property, Trump Castle, in Atlantic City, New Jersey. “I’d like to see the quality of the girls,” Trump said.

It was at this 1993 party that Trump is alleged to have sexually assaulted Houraney’s partner at the time, a businesswoman named Jill Harth. Trump is alleged to have openly expressed a sexual interest in Harth, noting to Houraney (who was dating Harth), “I’m going to go after her.”

According to Harth, from her testimony in her 1997 lawsuit against Trump, Harth alleged that Trump “…pushed me against the wall and had his hands all over me and tried to get up my dress again…,” in one of his children’s rooms at Mar-A-Lago, forcibly kissing and fondling her and restraining her from leaving the bedroom. Harth also alleged that Trump had previously groped her under a table at a dinner they both attended in 1992. Harth ended up marrying Houraney in 1995, dropping her suit in 1997 as part of a settlement tied to the settlement of Houraney’s own suit against Trump where he alleged Trump had cheated him out of a $250,000 fee as well as potential millions of dollars in future business profits. Houraney and Harth divorced in 1998.

“He’s a horrible human being. He does nasty things to his best friends, best friend’s wives, anyone who he first tries to gain their trust and uses it to do bad things to them.” - Jeffrey Epstein, describing to veteran journalist and author Michael Wolff how Trump enjoyed having sex with the wives of men he knew

Throughout their 15-year relationship, Epstein alleges that Trump was quite the manipulator. Epstein has described to Michael Wolff, who has interviewed Epstein extensively (accumulating nearly 100 hours of taped conversations over several years), how he and Trump would pick up women by combining to split them from their male companions, going to Atlantic City to try and find girls in Trump’s casino. According to Epstein, if Trump found a potential female target, he would lie and say he was there to invite the couple to dinner, but then turn to the woman and offer to give her a personal tour of the casino, putting his arm around her shoulders, which was a signal to Trump’s bodyguards to swoop in, allowing Trump to take the woman away.

When Trump fancied a friend’s wife or partner, Epstein detailed that Trump had an elaborate scheme to get them into his bed. Trump’s strategy was to invite the men to his office in Trump Tower and casually instigate a “locker room conversation” that eventually would touch on the men’s sex lives. Unbeknownst to the men, Trump would already have the men’s wives on speakerphone, listening in on the conversation. At some point, Trump would say things like, “You must have had a better f*** than your wife…tell me about it,” or “Do you like having sex with your wife? How often do you f*** her?” As the conversations progressed, Trump would set his trap by saying something to the effect of, “Well, you know, we can go upstairs, or tomorrow come over, I have this girl coming in from Los Angeles who is part of the Hawaiian Tropic contest. Come over, we can have a great time.” The wives would, of course, hear everything, and if these men responded positively to his offers, Trump would then use the wives’ anger at their husbands’ potential infidelity to seduce them into bed. As Epstein tells it, this was a regular thing for Trump, who particularly enjoyed it.

“A funny New York thing…”

It was Spring of 1996 when Trump allegedly sexually assaulted E. Jean Carroll, an advice columnist and writer for Elle and New York magazines. The two were socially familiar with each other in New York and had been photographed together at a party in 1987. According to Carroll, the two encountered each other while shopping at Bergdorf Goodman in Manhattan. There Trump stopped her and asked for her help picking out a gift for another woman. The interaction started out in the hat section, with Carroll encouraging Trump’s playful banter, viewing their back and forth as a “funny New York thing” and a “wonderful prospect” as an advice columnist. At some point, they found themselves in the lingerie department where they playfully dared each other to try on see-through bodysuits. According to her testimony, Carroll followed Trump’s lead and joined him in a dressing room, still teasing and daring each other to try on the lingerie, describing the situation as “flirtatious frivolity,” comparing the overall atmosphere between the two to a Saturday Night Live skit she might have written. Once inside the dressing room, Trump allegedly shut the door, pushed Carroll against a wall, and sexually assaulted her.

In 2023, a federal jury found Trump liable for sexual abuse and defamation. While the jury did not feel that Carroll’s testimony proved beyond a reasonable doubt that Trump had raped her (under New York’s narrow definition of rape, which requires “penile penetration’), Judge Lewis Kaplan clarified that the jury’s finding implicitly determined “forcible digital penetration which he described as constituting “rape” in common language, just not per New York state law.

E. Jean Carroll was awarded $83.3 million dollars in part due to Trump’s incessant public attacks, which Judge Kaplan described as “remarkably high, perhaps unprecedented” in their degree of malice and “reprehensibility.” Trump has appealed the verdict several times, so far to no avail. Trump continues to log appeals and has posted a bond of nearly $92 million to be held in escrow while the appeals process continues (with interest, the original award of $83.3 million has reached almost $90 million as of late 2025). Carroll is on record as saying she will donate funds to causes she knows Trump “hates” should she end up seeing anything from the case.

"Epstein and Trump — Love Interrupted" is a love story presented in three parts. Read Part Two here, and Part Three here.

Author

Sean Thompson

Club Member, Democratic Club of Greater Tracy