At the heart of the documents connected to a 2015 defamation case are allegations by a woman, Virginia Roberts Giuffre, who has claimed that Epstein kept her as a teenage "sex slave" and that he was assisted in his efforts by a British woman, Ghislaine Maxwell.
Epstein pleaded not guilty in July to charges from New York federal prosecutors after an indictment accused him of sex trafficking dozens of underage girls, some as young as 14 years old. Maxwell hasn't been charged.
An attorney for Maxwell did not respond to CNN's request for comment Friday. Maxwell and her representatives have previously denied she engaged in sexual abuse or sex trafficking.
The documents unsealed Friday were produced as a result of a lawsuit Giuffre filed against Maxwell, nearly two decades after her alleged abuse. They include new allegations by Giuffre that she was instructed by Maxwell to have sex with former New Mexico Gov. Bill Richardson and former US Sen. George Mitchell, among others.
In a statement Friday, Mitchell called the claim false, adding: "I have never met, spoken with or had any contact with Ms. Giuffre."
A spokeswoman for Richardson called Giuffre's allegation "completely false."
"To be clear, in Governor Richardson's limited interactions with Mr. Epstein, he never saw him in the presence of young or underage girls," spokeswoman Madeleine Mahony said. "Governor Richardson has never been to Mr. Epstein's residence in the Virgin Islands. Governor Richardson has never met Ms. Giuffre."
The documents also include an Amazon receipt recovered from the trash at Epstein's Palm Beach mansion for books ordered in his name, including "SM 101: A Realistic Introduction," "SlaveCraft: Roadmaps for Erotic Servitude" and "Training with Miss Abernathy: A Workbook for Erotic Slaves and their Owners."
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. The records show Giuffre had complained of irregular vaginal bleeding for three weeks; had fainted two days prior, falling and hitting her head; and had lost seven pounds in the past month.
CNN has reached out to the hospital to ask whether it flagged the incident to authorities.
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. It was biological. Like eating."
The US Court of Appeals for the Second Circuit unsealed the documents, ruling that the judge in the defamation case had improperly sealed hundreds of filings. That judge has since died.
The defamation case was settled in 2017, after the judge had ruled against a motion for summary judgment filed by Maxwell.
An attorney for Epstein, Reid Weingarten, didn't immediately respond to a request for comment Friday, nor did an attorney for Maxwell. In the court filings, Maxwell and her attorney portray Giuffre as an unreliable narrator, pointing to errors in certain dates and figures she provided.
Giuffre has said the errors were mistakes.
David Boies, an attorney for Giuffre, said Friday that her lawsuit "exposed for prosecutors, and now the public, the scope and scale and ugliness of the Epstein/Maxwell sex trafficking ring."
The charges in the July indictment of Epstein share similarities with Giuffre's account, but it's not clear whether she is among any of the unnamed victims in that indictment.
But Giuffre is arguably the best-known of Epstein's alleged victims because she has claimed that Epstein forced her as part of her servitude to perform sex acts with a number of prominent men, including Prince Andrew, Duke of York, in 2001. She has also made claims of being sexually abused by lawyer Alan Dershowitz.
Dershowitz, who was part of the legal team that negotiated a controversial 2007 deal that allowed Epstein to avoid federal prosecution for sex trafficking in Florida and instead plead guilty to lesser state charges, has denied her claims and accused her of fabricating the allegations against him.
Friday, he said in a statement that the fresh batch of documents "categorically proves that Virginia Roberts never had sex with me."
In April, she filed a separate defamation lawsuit against him. That case is ongoing; Dershowitz has filed a motion to dismiss.
In the documents unsealed Friday, the other woman who alleged abuse at the hands of Epstein and Maxwell also claims she was forced into sexual acts with Prince Andrew at Epstein's Upper East Side mansion, where, she said, Giuffre participated as well.
In response, a spokesperson for Buckingham Palace said: "This relates to proceedings in the United States, to which The Duke of York is not a party. Any suggestion of impropriety with underage minors is categorically untrue."
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. The Duke has not met with Mr Epstein since."
With regard to President Donald Trump, who socialized with Epstein in the 1990s and once described him as a "terrific guy" before the two, in Trump's recollection, had a falling out 15 years ago, Giuffre distances Trump from Epstein's alleged affairs.
According to a transcript of a video deposition Giuffre gave in 2016, she disputed aspects of a 2011 story in the Daily Mail that was based on a series of interviews Giuffre had given to one of the reporters, Sharon Churcher.
The story quotes Giuffre as saying: "Donald Trump was also a good friend of Jeffrey's. He didn't partake in sex with any of us but he flirted with me. He'd laugh and tell Jeffrey, 'You've got the life.'"
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. Donald Trump never flirted with me." She also says her only basis for stating that Trump was a "good friend" was Epstein's own description of his relationship with Trump.
Asked whether she ever saw the two men together, Giuffre replies, "No, not that I can actually remember." She also says she can't recall ever having seen Trump at Epstein's homes in the US Virgin Islands, New Mexico or New York.
But she did not refute other details of the Daily Mail story, including that Epstein hosted a dinner on his Caribbean island for President Bill Clinton shortly after Clinton left office.
Asked for comment, a spokesman for Clinton said he had never been to Little St. James, the island Epstein owns in the Caribbean. In July, in the wake of the indictment against Epstein, the spokesman, Angel Urena, acknowledged that Clinton had taken a handful of trips on Epstein's plane, but said that "President Clinton knows nothing about the terrible crimes Jeffrey Epstein pleaded guilty to in Florida some years ago, or those with which he has been recently charged in New York."
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