Jeffrey Epstein & Donald Trump: An Analysis

Trump later recounted knowing Epstein for 15 years, indicating their relationship started in the late 1980s. Jack O’Donnell, former president of Trump Plaza Hotel, frequently saw them together, even calling Epstein Trump's "best friend." O'Donnell also described an incident where Trump brought Epstein and a 19-year-old girl to the casino gaming floor.

This move further cemented their social circles, leading to more frequent encounters at parties and events in both New York and Florida, as they lived blocks apart in New York and two miles apart in Florida.

Williams later described Trump and Epstein as "really, really good friends" who spent a lot of time together. Three months later, Epstein took Williams to Trump Tower, where she says Trump groped her while laughing with Epstein, an activity she has said she thought was “a twisted game” between the men.

Houraney recounted bringing "28 girls" to the event exclusively for Trump and Epstein. Jill Harth, Houraney's then-girlfriend and business partner, alleged Trump assaulted her that evening, forcibly kissing and fondling her in Ivanka’s bedroom and even restraining her from leaving as she protested. Harth also said Trump later crawled into the bed of a 22-year-old contestant uninvited.

Photos show Epstein clad in white pants and a bow tie at the high-profile event. Later that year, they were photographed at a Harley-Davidson Cafe with Trump's children.

According to Epstein, Trump first slept with Melania Knauss on his private jet. Trump flew on Epstein's plane eight times between 1993 and 1997, sometimes with his family members, underscoring the private and frequent nature of their interactions.

Farmer, then in her mid-20s, recalled Trump staring at her legs in a threatening way until Epstein intervened, saying, "No, no. She's not here for you." Trump was then overheard saying he thought Farmer was 16 years old. According to Michael Wolff, Trump and Epstein competed to date the hottest models, and sometimes shared or traded girls between them.

This event, held at Club Duvet on 21st St in NYC, along with others, demonstrates their presence in similar social circles, often involving models and celebrities. The photo is unposed, and Epstein’s signature smirk is visible right beside Trump’s profile.

Giuffre, then 16, later accused Epstein and Maxwell of years of sexual abuse. This event became central to Trump's shifting explanations for his falling out with Epstein. Giuffre's employment at Mar-a-Lago in summer 2000 was confirmed by Social Security records. Giuffre died by suicide in April 2025 at the age of 41.

This widely cited quote underscores the nature of their public relationship before Epstein's legal troubles became widely known. Trump's statement reflected an early, positive public perception of Epstein.

The card reportedly included a drawing of a naked woman and a dialogue where Trump states, "We have certain things in common, Jeffrey," and Epstein replies "Yes, we do, come to think of it." The dialogue concludes with Trump saying: "A pal is a wonderful thing. Happy Birthday – and may every day be another wonderful secret." Trump immediately denied having written the letter and sued The Wall Street Journal for defamation.

The dispute over the $41.35 million oceanfront property is cited by several sources as the reason for their rupture. Phone records reportedly show a cessation of communication after this event. Trump later sold the mansion for $95 million to a Russian billionaire in 2008, making a substantial profit.

This is another widely cited reason for their falling out, with Mar-a-Lago records showing Epstein's account closed in October 2007. Trump reportedly told lawyer Brad Edwards this reason in 2009. The teenage girl was reportedly working as a masseuse in the spa when Epstein behaved inappropriately.

This plea deal, approved by then-U.S. Attorney Alexander Acosta, allowed Epstein to avoid federal prosecution for victimizing multiple underage girls. Acosta would go on to be appointed as Labor Secretary by Trump nearly a decade later.

Epstein also claimed to have been Trump's "closest friend for 10 years" and boasted of intimate knowledge of Trump's proclivities, including an alleged claim that Trump first slept with Melania Knauss on Epstein's private jet. Trump's camp dismissed these as "false smears" and "election interference."

This statement marked a significant shift in Trump's public stance on his relationship with Epstein, attempting to distance himself from the disgraced financier. This claim would place the end of their friendship around 2004.

This statement drew criticism given Maxwell's role as Epstein's alleged accomplice in sex trafficking. Trump later doubled down, saying, "I'd wish a lot of people well. Good luck. Let them prove somebody was guilty."

This statement, made amid renewed scrutiny, contradicted previous accounts and raised questions about Trump's prior knowledge of Epstein's activities. Giuffre's family responded, highlighting inconsistencies, as Epstein remained a Mar-a-Lago member until 2007, seven years after Giuffre's recruitment.