The allegation surfaced in a cache of legal papers unsealed by a United States judge in a defamation case involving a British socialite alleged to have supplied Epstein with underage girls.
"I've known Jeff for 15 years", Trump told NY magazine in 2002. Flight logs have revealed the former U.S. president took trips on Epstein's private plane, reportedly nicknamed the "Lolita Express".
Virginia Giuffre, Epstein's self-described "sex slave", married an Australian man and now lives in Queensland.
Other documents show testimony from another woman who has alleged abuse at the hands of Epstein and Maxwell, and claimed in a deposition that Epstein told her that "in his opinion, he needed to have three orgasms a day".
Epstein was previously arrested over a series of allegations of sexual misconduct from at least 2002 to 2005.
A woman who has long claimed that Jeffrey Epstein and socialite Ghislaine Maxwell kept her as a "sex slave" alleges the duo forced her to have sex with two prominent Democratic politicians: George Mitchell and Bill Richardson.
A partial transcript of a September 2016 deposition in a lawsuit was included in hundreds of pages of documents placed in a public file by a federal appeals court in NY.
The documents disclose Giuffre's 2001 medical records from a hospital that she said Epstein and Maxwell took her to during a period of sexual abuse.
Giuffre has said the errors were mistakes.
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Epstein was charged with one count of sex trafficking of minors and one count of conspiracy to engage in sex trafficking of minors. He faces more than 40 years in prison if convicted.
She claims, as the then 21-Year old, together with Giuffre, 2001 in Epstein's apartment in NY of Prince Andrew " groped been: "there are also several eye-witnesses".
"Gruesome Jeffrey Epstein docs unsealed this a.m. Ghislaine Maxwell punished underage girls who didn't make Epstein orgasm, etc.", wrote journalist Vanessa Grigoriadis. Buckingham Palace strongly denied the allegation in 2015, saying in a statement that "any suggestion of impropriety with underage minors" by the prince was "categorically untrue".
The records contain graphic allegations against Epstein who pleaded not guilty to sex trafficking charges.
In a statement to CNN last month, the spokesperson said, "The Duke of York accepts it was unwise to have met Mr. Epstein in December 2010".
Epstein had been behind bars since his arrest on July 6.
In the deposition, Giuffre says "it's true that he didn't partake in any sex with us, (but) it's not true that he flirted with me".
The connections were revealed in a cache of almost 2,000 documents that federal prosecutors with the Southern District of NY unsealed Friday.
Epstein's lawyers say the federal charges that accuse Epstein of recruiting and abusing dozens of underage girls in NY and Florida in the early 2000s should never have been brought.