A fresh trove of emails has shed new light on the often rocky relationship between Jeffrey Epstein and one of his longest-standing Wall Street benefactors.
The messages, reviewed by the New York Times, reportedly reveal how Epstein could often be spiteful, even “cruel” toward Leon Black. A multi-billionaire hedge fund manager, Black was ousted as CEO of Apollo Global Management in 2021 after it emerged he’d continued to pay the late pedophile tens of millions of dollars for financial services for well over a decade after Epstein’s abuse of underage girls first came to light.
“I mean, he was with a 17-year-old prostitute, got prosecuted for it and got put away for a year,” Black told Puck magazine last year of Epstein’s 2008 conviction for soliciting prostitution from a minor. “I didn’t think it was the end of the world, frankly.”

Between 2015 and 2016, the emails obtained by the NYT reportedly show how Epstein mounted a “pressure campaign” on Black to keep the cash coming, describing the work of Black’s other advisers as “a really dangerous mess” and a “waste of money and space.”
Part of that campaign appears to have involved direct attacks on Black’s family. “At least for a few weeks I am unable to commit much time and make any future plans to guide you in the redoing of your procrastination produced mess,” the late pedophile wrote in one November 2016 missive about Black’s estate. “You have a bomb of colored string that your retarded children have formed. It has to be very carefully unwound.”
Despite the tenor of these messages, the hedge fund manager kept up payments to Epstein, which the NYT reports eventually totalled $170 million, for a further two years, with the late pedophile demanding the lion’s share of his costs be met up front.

“I never want to have any more uncomfortable money moments with you, I find it very distasteful,” Epstein wrote in 2015. “So to be clear, my terms are as follows. I will only work for the usual 40 million per year. It needs to be paid, 25 million upon signing an agreement.”
On other occasions, Epstein appears to have emphasised that he didn’t feel his financial dealings with Black to be the sum of their relationship. “Of course re any non financial issues, I am always there for you and will continue to be the best friend I can be,” as he reportedly put it.
The NYT’s report suggests Epstein introduced Black to a number of young women over the years, some of whom would later accuse Black of sexual abuse.

Citing court documents and notes taken by Congressional investigators, the newspaper identifies one of those women as Cheri Pierson, whom Epstein had at one time paid for massage services, who reportedly claimed in a lawsuit she had been introduced to Black at Epstein’s Manhattan townhouse in 2002, where she said Black raped her in the massage room. Black denied Pierson’s claims, which were later withdrawn.
On another occasion, Epstein is understood to have advised Black on payments of $10 million to another woman, Guzei Ganieva, after she accused Black of sexual assault. Black has reportedly acknowledged having an extramarital affair with Ganieva, but denied assaulting her.
Congressional investigators have apparently also raised concerns over millions of dollars paid by Black to at least eight women who were later listed among Epstein’s associates and victims in court filings. Black has apparently declined to comment on the purposes of those payments.

Epstein’s case is back in the spotlight after the MAGA Justice Department and FBI determined earlier this year his 2019 death in police custody on sex trafficking charges was a suicide, and that he kept no “client list” of uber-wealthy associates.
Those findings flew in the face of President Donald Trump’s longstanding courtship of far-right conspiracy theorists who believe Epstein and his co-conspirator Ghislaine Maxwell, who’s currently serving a 20-year sentence, were members of an international pedophilic cabal.
Trump has since faced renewed scrutiny of his own once-close relationship with Epstein, not least given his refusal to rule out a prospective pardon for Maxwell after her comments, made during a jailhouse interview with DOJ officials this summer, seemingly exonerating the president of any impropriety. Trump has further sought to deflect that scrutiny by insisting other “hedge fund guys” had a far closer relationship with Epstein than he ever did.
Earlier this summer, Trump sued the Wall Street Journal for $10 billion after the newspaper reported he had contributed to a book of greetings to commemorate Epstein’s 50th birthday in 2003, with his card featuring a crude sketch of a nude woman and a bizarre imagined exchange about “enigmas” and “wonderful secrets.”
Black contributed to the same book, the NYT now reports. His entry, a handwritten poem featured in full in the newspaper’s article, includes the lines: “Blonde, Red or Brunette, spread out geographically / With his net of fish, Jeff’s now ‘The Old Man and the Sea’.”
The Daily Beast has reached out to Black’s representatives for comment on this story. “After an exhaustive investigation more than four years ago, the Dechert law firm concluded that Mr. Black paid Epstein only for tax and estate planning advice that saved him and his family billions of dollars,” his lawyer, Susan Estrich, said. “To imply that Epstein somehow had influence over Mr. Black is false and patently absurd. Indeed, it was Mr. Black who fired Epstein because he was disruptive and believed the fees for his services were excessive.”
“The Dechert Report also found that Mr. Black had no knowledge of Epstein’s criminal activities. Mr. Black has never abused a woman in his life and any such suggestion is false,” she went on. “Moreover, it is irresponsible and unethical for The New York Times to have Matt Goldstein working on this story. Mr. Goldstein actively advised Guzel Ganieva, which we learned through dozens of emails and text messages found in discovery. Her complaint was ultimately dismissed with prejudice and the decision upheld by the appellate court.”
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