The resurfacing of a controversial birthday letter has renewed scrutiny over the relationship between Donald Trump and the late financier Jeffrey Epstein. Despite Trump’s denials, years of public appearances, social events, and overlapping social circles indicate that the two were once closely acquainted.
Their connection appears to date back to the 1980s, during which Trump was a rising real estate mogul. The two moved in similar high-society circles, attending exclusive parties in New York and Palm Beach. By 2002, Trump openly spoke about Epstein, calling him a “terrific guy” and acknowledging that they shared a mutual appreciation for beautiful women, some “on the younger side.”
Throughout the 1990s, Trump and Epstein were regularly seen together. They were photographed at numerous events, including a 1992 Mar-a-Lago party and Victoria’s Secret shows in 1997. Flight records show that Trump flew on Epstein’s private jet multiple times between 1993 and 1997, on routes between Palm Beach, New York, and Washington, DC.
In 2000, they were pictured again at Trump’s Mar-a-Lago estate in Florida. The event included several high-profile guests, including Melania Knauss, Trump’s then-girlfriend, and Ghislaine Maxwell, Epstein’s close associate. Around this time, court documents would later show, Epstein and Maxwell were allegedly grooming young girls, some of whom had worked at Mar-a-Lago.
By 2003, a collection of Epstein’s birthday letters reportedly included one signed by Trump. The note, allegedly compiled by Maxwell, featured third-person banter and a suggestive illustration. Trump has since denied authoring the letter or the drawing, publicly calling the claims fabricated and threatening legal action against the publication that reported it.
Their relationship soured in 2004 after a real estate dispute over a Palm Beach mansion, reportedly creating a rift between them. After this, their public interactions appear to have ended. By 2005, Epstein was under police investigation for sexually abusing underage girls. Despite the gravity of the charges, a controversial plea deal in 2008 allowed him to serve minimal jail time.
In 2019, Epstein was arrested again, this time on federal sex trafficking charges. His death in custody that same year fueled widespread conspiracy theories. When asked about Epstein at the time, Trump distanced himself, claiming he hadn’t spoken to him in over a decade and had had a falling out long before.
In 2024, court documents revealing names of Epstein associates mentioned Trump, though he was not accused of wrongdoing. The revelations intensified public curiosity, particularly among Trump’s political supporters, some of whom subscribe to conspiracy theories regarding Epstein’s death and alleged client list.
In response to recent attention, Trump has expressed frustration, distancing himself further from the case and condemning the narrative as politically motivated. He directed the Justice Department to seek the unsealing of grand jury testimony to disprove the allegations, while simultaneously lashing out at supporters who promote conspiracy theories involving him and Epstein.
Despite his efforts to dismiss the connection, the historical record — filled with photos, party appearances, and mutual acquaintances — suggests that Trump and Epstein were, for a time, close associates.
