New documents show volatile evolution of Trump-Epstein relationship

On Friday, January 30, the U.S. Department of Justice (DOJ) publicly released 3 million more documents related to its investigations of the late billionaire financier and convicted sex offender Jeffrey Epstein. And many of them discuss Epstein's relationship with now-President Donald Trump.

In a timeline released on February 2, Forbes reporters Sara Dorn and Alison Durkee offer a timeline of that relationship based on the newly released DOJ files — which, they say, shows how Epstein and Trump went from being on very friendly terms to having a major falling out.

The documents, according to Dorn and Durkee, show that Trump and Epstein "met around the time Trump bought Mar-a-Lago in 1985" and continued to have a friendly relationship in the 1990s. In a 2002 interview with New York Magazine, Trump described Epstein as a "terrific guy" and said they had known one another for "15 years."

During the mid-to-late 1990s, according to the DOJ files, Trump and Epstein "talked at least three times a week."

In 2000, according to Dorn and Durkee, "Epstein victim Virginia Giuffre was working at Trump's Mar-a-Lago resort when she was recruited by (Ghislaine) Maxwell to work as Epstein's personal masseuse and was groomed by Epstein and Maxwell to provide sexual services for Epstein and his wealthy circle, according to a deposition Giuffre gave that was made public in 2019."

But in 2004, Dorn and Durkee report in their timeline, "Trump and Epstein had a falling out when Trump outbid him for a Palm Beach mansion, according to a Washington Post report."

In 2007, according to the reporters, "Trump's Mar-a-Lago club claimed Epstein had been banned from the property, with a source telling Page Six that Epstein 'would use the spa to try to procure girls' and asked one 18-year-old masseuse to 'do things,' adding, 'Her father found out about it and went absolutely ape-[bleep].'"

Forbes' timeline is consistent with what Michael Cohen, Trump's former personal attorney and fixer, said about Epstein during a July 20, 2025 appearance on MS NOW (then-MSNBC).

Cohen recalled, "I fell into Trump's orbit around 2005, but I became part of the Trump Organization as the executive vice president and special counsel in 2007. From the time that I started to the time that I finished in 2018, I actually never heard him mention Jeffrey Epstein at all. I never saw Jeffrey Epstein in the office…. I never heard Jeffrey Epstein on the phone or even call into the office. There was no relationship, from the time I started at the org to the time that I left."