In October 2017, a yoga instructor emailed Jeffrey Epstein with a delicate question: When might she receive the tens of thousands of dollars she’d been promised by the billionaire Leon Black?
She and Mr. Black had been in a sexual relationship, and since at least 2009, hundreds of thousands of dollars had flowed to her from Mr. Black’s bank accounts. But in 2017, the setup changed. Now Mr. Epstein would wire the money — in this case, $100,000.
“He said that now he does it through you,” the woman wrote to Mr. Epstein in an email that the Justice Department released this year. Mr. Epstein wrote back, confirming the arrangement.
In the later years of Mr. Epstein’s life, after he was incarcerated and registered as a sex offender, no one did more to bankroll his opulent lifestyle than Mr. Black, 74, a towering figure on Wall Street and a fixture of the global art scene.
Mr. Black paid Mr. Epstein $170 million over six years for what Mr. Black has said were tax and estate-planning services. The sum dwarfed what elite law or accounting firms would have charged for similar work, baffling both his Wall Street peers and investigators on Capitol Hill.
The millions of pages of Epstein-related emails and other documents that the Justice Department released this year offer a potential explanation for the size of the payments: Mr. Epstein essentially served as a fixer whose services went beyond modernizing Mr. Black’s finances or reducing his taxes, according to a New York Times review of those records.
Mr. Epstein suggested ways to obscure millions of dollars that Mr. Black paid to women, as well as to Mr. Epstein himself. He brainstormed about how to avoid taxes on some of the payments. He took credit for defusing a government audit of a woman to whom Mr. Black had paid millions of dollars. He planned ways to surveil, intimidate and silence another woman who was threatening to publicly accuse Mr. Black of abuse. He even counseled Mr. Black to separate from his wife after she learned of his infidelity.
Mr. Black paid about $20 million to a dozen women, at least some of whom he’d had sexual relationships with, according to the recently released files and notes taken by congressional investigators and shared with The Times. Mr. Epstein was involved in figuring out ways to dispense a significant portion of that money.
Mr. Epstein summed it up to Mr. Black in a 2017 email: Mr. Epstein’s job, as he saw it, was partly about “saving you from yourself.”
In a statement, Mr. Black’s lawyers, Courtney Forrest and Susan Estrich, said the Justice Department documents “make clear that Mr. Epstein embellished, exaggerated and lied about Mr. Black.” They said Mr. Black was not aware of Mr. Epstein’s sex trafficking or that he paid any women on Mr. Black’s behalf.
The recently released documents, which include some of Mr. Black’s financial records, have intensified congressional scrutiny of his relationship with Mr. Epstein and whether it crossed ethical or legal boundaries.
The House Oversight Committee recently asked Mr. Black to sit for an interview. Senator Ron Wyden, an Oregon Democrat who has been investigating Mr. Black’s financial ties to Mr. Epstein for years, accused him in a letter last week of seemingly using Mr. Epstein to hide payments to women. He also questioned whether Mr. Black had complied with tax laws.
In an interview, Mr. Wyden said that he had never believed that Mr. Black paid Mr. Epstein $170 million solely for estate and tax advice. “I think this all comes down to hush money,” he said, as well as Mr. Epstein doing “the kinds of things that would keep Black ahead of the law.”
Ms. Estrich said that Mr. Wyden’s claims were “outrageous and false” and were meant to serve “his own selfish political interests.” She accused him of leaking Mr. Black’s confidential financial information and of trying to distract from the fact that Mr. Wyden’s son, a hedge fund manager, sought an investment from Mr. Epstein in 2016.
Mr. Wyden said his son’s presence in the Epstein documents would not change the course of his investigation.
‘Happy Days’
Mr. Epstein and Mr. Black first met in the mid-1990s, not long after Mr. Black co-founded the private equity firm Apollo Global Management. The two became friends.
Mr. Black and his wife, Debra, named Mr. Epstein to the board of their family foundation. In 2003, Mr. Black was among the contributors to a book celebrating Mr. Epstein’s 50th birthday, signing his entry “Love and Kisses.”
Six years later, when Mr. Epstein was released from jail after serving time for soliciting prostitution from a minor, Mr. Black was eager to celebrate. An assistant informed Mr. Epstein that Mr. Black wanted to sing him “Happy Days Are Here Again.”
“If i have to listen i’d rather be in jail,” Mr. Epstein replied.
On several occasions, Mr. Epstein introduced Mr. Black to women, according to emails and investigative records released by the Justice Department, as well as interviews with lawyers involved in Epstein cases. At least three of the women later accused Mr. Black of rape or sexual assault, allegations that he has denied. “Mr. Black has never abused, assaulted or raped any girl or woman, and the idea of doing so is repulsive and reprehensible to him,” his lawyers said.
The Manhattan district attorney’s office briefly investigated sexual assault allegations against him; no charges were filed. The U.S. Virgin Islands conducted a civil investigation of Mr. Black’s relationships with Mr. Epstein and several women. Mr. Black paid $62 million in a settlement with the territory before it made any public accusations.
By 2012, the friendship between the two men had also become a business relationship.
Mr. Black, who at the time was worth about $3.4 billion, was dealing with some complex tax issues.
That year, Mr. Epstein helped devise a way to restructure a trust and save Mr. Black hundreds of millions of dollars in taxes. While it is unclear to what degree the idea originated with Mr. Epstein or Mr. Black’s other advisers, it cemented Mr. Epstein’s value in his eyes.
A law firm that Apollo hired to review the Black-Epstein relationship later characterized Mr. Epstein’s work on the trust as the most important service that he had provided to Mr. Black. (He stepped down from Apollo in 2021.) The law firm, Dechert, concluded that Mr. Epstein’s tax and estate-planning services had been legitimate and vetted contemporaneously by well-qualified lawyers.
But other assignments that were not mentioned in Dechert’s 2021 report had been much more sensitive.
For years, Mr. Black had been paying women — some of them hundreds of thousands of dollars annually, according to the Justice Department’s Epstein documents, court filings, Mr. Wyden’s letter and two of the lawyers involved in Epstein cases.
For tax purposes, Mr. Black classified many of the payments as gifts. The recipient of a gift generally does not need to pay taxes on it. The giver does not need to pay taxes, either, until his lifetime giving exceeds a certain amount. The threshold varies by year, but in 2012, the limit was about $5 million — and Mr. Black had surpassed it, emails show. That meant that he would have to start paying a 40 percent tax on any large gifts.
Mr. Epstein suggested that because at least some of the gifts had come from a bank account that Mr. Black held jointly with his wife, perhaps half could be attributed to her for tax purposes. That would increase Mr. Black’s capacity to make tax-free gifts.
One of Mr. Black’s accountants shot down the idea, noting that because Ms. Black had no involvement in the gifts to the women, it would probably violate federal tax law.
But the question was not only how much Mr. Black might owe in taxes. It was also what he and the women would have to disclose to the Internal Revenue Service. If the payments were not gifts, the women would need to report the money as income on their tax returns. If the payments were gifts, Mr. Black would have to disclose them on a gift-tax return.
A rule of thumb for the ultrawealthy is to “limit unnecessary paper trails, which create opportunities for misunderstanding, audit risk and reputational exposure,” said Victoria J. Haneman, a professor at the University of Georgia School of Law who specializes in taxes and estates.
In late 2012, Mr. Epstein and Mr. Black’s other advisers discussed a strategy: Mr. Black could donate money to a family trust, and the trust could then make additional gifts. Mr. Black would still owe taxes, but payments would no longer come directly from him.
Going forward, his payments to at least some women came from several trusts he controlled, emails and financial documents show.
Mr. Black’s lawyers said that all of his payments to women and gift taxes “were vetted and approved by legal and accounting experts.” They added, “Evidence that communications were sent to Mr. Black is not evidence that he read, agreed with or followed advice in those messages.”
Secret Lunch Recordings
While Mr. Epstein kept advising Mr. Black on financial matters, he was also branching into less conventional fare.
Mr. Black had a long-running affair with a Russian woman, Guzel Ganieva. By 2015, she was threatening to go public with allegations of sexual abuse unless he paid her $100 million, according to the Justice Department’s Epstein documents and interviews with people familiar with her claims. Mr. Epstein was there to help.
That July, after the two men met, Mr. Epstein drafted a menacing email that was apparently meant for Mr. Black to send to Ms. Ganieva, who at the time was in her 30s.
“I felt it necessary to contact some friends in FSB,” the message read, referring to the Russian security service. The message warned that her attempts to “blackmail a us businessman” would be viewed in Russia, which was trying to attract Western investments, as a grave threat and would be “dealt with extremely harshly.”
The message suggested that Mr. Black could pay her $50,000 a month for two years. “I expect never ever to hear a threat from you again,” Mr. Epstein wrote in Mr. Black’s voice.
There is no indication that Mr. Black read the message, which Mr. Epstein sent to himself, or that it was sent to Ms. Ganieva. But it became something of a playbook for Mr. Epstein in the weeks ahead.
Later that month, he emailed Sergei Belyakov, a well-connected Russian government official, to request a favor. He explained that Ms. Ganieva had tried to blackmail “a group of powerful biznessman in New York. It is bad for business for everyone involved.” Mr. Epstein asked if he had any suggestions.
Mr. Belyakov responded by leveling damaging personal allegations against Ms. Ganieva and said that limiting her access to the United States “would be a great threat to her business.”
At the time, Mr. Epstein was in regular contact with Brad Karp, the chairman of the law firm Paul Weiss and one of Mr. Black’s most trusted advisers. Mr. Epstein and Mr. Karp discussed whether they could somehow block Ms. Ganieva from the United States, which she had most recently entered on a tourist visa.
Another possibility was to enlist law enforcement. “Your call on fbi or nypd,” Mr. Epstein wrote to Mr. Karp, proposing that Ms. Ganieva be arrested after Mr. Black “passes her a large check. Grand larceny etc.” (There is no indication that they went to law enforcement at the time.)
Mr. Epstein tracked down information about Ms. Ganieva’s whereabouts, her acquaintances and even her young son. He suggested to Mr. Karp that Mr. Black enlist private investigators from Nardello & Co.
The Nardello investigators soon began running surveillance on Ms. Ganieva. And in August, they put in motion a plan to secretly record a series of meetings between Mr. Black and Ms. Ganieva at posh New York restaurants. The goal was to capture her on tape acknowledging that Mr. Black had not abused her. Emails show that Mr. Epstein and Mr. Karp strategized before and after some of the encounters.
Over meals at the Four Seasons, Le Bernardin and the Modern, Mr. Black increased the amount of money he was offering Ms. Ganieva — while sprinkling in threats about her ending up in jail if she didn’t stop threatening him, according to transcripts of the recordings.
Mr. Epstein suggested raising the offer to $100,000 a month for years into the future — a proposal that appears to have carried the day. The final deal, struck in October 2015, called for Mr. Black to pay Ms. Ganieva a total of $18 million over the next 15 years. In return, she signed a nondisclosure agreement in which she said that allegations she had made against Mr. Black were “not true.”
Mr. Epstein appeared to be involved in setting up the payments to Ms. Ganieva through a generically named trust, emails show.
His work on the Ganieva matter was not mentioned in the Dechert report.
‘Avoid Public Disclosure’
The same month as the deal with Ms. Ganieva, Mr. Black and Mr. Epstein worked out an agreement of their own. It involved a payment of $20 million in fees to Mr. Epstein.
The plan appeared to be structured at least in part to avoid taxes.
Mr. Black would pay $10 million to Mr. Epstein’s primary company, Southern Trust. But the other $10 million would be in the form of a donation to one of Mr. Epstein’s charitable organizations, Gratitude America, which until then did not have any funds.
Gratitude America soon began dispensing the money in ways that could burnish Mr. Epstein’s reputation or strengthen his ties to figures in academia and other fields.
There were benefits for Mr. Black, too. Mr. Epstein’s accountant, Richard Kahn, noted in an email to one of Mr. Black’s advisers that a goal of the arrangement was “to maximize deductions.” Mr. Black would be able to write off the $10 million and potentially lower his tax bill.
The catch was that private foundations like Gratitude America have to file public reports disclosing their donors.
“In an effort to avoid public disclosure of Leon name, this charitable donation should be paid from your LLC that owns automobiles,” Mr. Kahn wrote to Mr. Black’s adviser. Ultimately the money would come from a different entity, BV70 LLC, that had been set up to own Mr. Black’s yacht.
While the emails between aides to Mr. Epstein and Mr. Black describe the donation as part of a fee payment, the Dechert report implied that it was simply an act of charity: Mr. Black “felt comfortable making this donation because he understood that Epstein was a strong proponent of scientific innovation.”
Mr. Wyden, in his letter to Mr. Black, said the emails pointed to possible illegality. “Intentionally disguising payments for professional services as charitable contributions to claim a tax deduction would constitute tax fraud,” he wrote.
Mr. Wyden said in the interview that the Dechert report appeared to whitewash some of Mr. Black’s actions.
An Apollo spokeswoman said Dechert’s review was “thorough and independent.”
An I.R.S. Audit
Mr. Black’s voluminous gift-giving drew the attention of the I.R.S. Starting in 2016, the agency began auditing Mr. Black and a woman named Anastasiya Siro, with whom he’d been having an affair, according to the Justice Department documents and two people familiar with the relationship.
Mr. Epstein worked with Mr. Black’s accountants on audits of the billionaire’s taxes, but he appeared to be especially enmeshed in the audit of Ms. Siro, a former model from Ukraine. Mr. Epstein had known her since at least 2010, when she was in her early 20s. (Representatives for Mr. Black and Ms. Siro said they did not meet through Mr. Epstein.)
Recently released records show that Mr. Black was paying her millions of dollars.
The I.R.S. was focused in part on more than $600,000 that Ms. Siro had received from one of Mr. Black’s trusts. She had not paid taxes on the payments, because she considered them gifts, the emails show.
An I.R.S. auditor wanted to review Mr. Black’s gift-tax return to see if he, too, had classified them as gifts. The auditor also sought to interview Ms. Siro about her relationship with Mr. Black, who had helped set her up as an art dealer, records show.
As Mr. Epstein sought to resolve Ms. Siro’s audit, he acted as a liaison between her and Mr. Black’s advisers. Mr. Epstein arranged for Mr. Black’s accountant to write a letter to the I.R.S. auditor confirming that the payments had been gifts.
Mr. Epstein spent months dealing with the Siro audit, and when it appeared to get resolved, he took credit.
A spokesman for Ms. Siro said Mr. Epstein helped with the audit because he was a tax expert. “After the audit was complete, she had nothing more to do with Epstein,” he said.
The report that Dechert prepared for Apollo noted that Mr. Epstein had helped deal with a number of I.R.S. audits of Mr. Black. It did not mention his role in the audit of Ms. Siro.
Mr. Epstein’s involvement in personal matters was only increasing. After Ms. Black learned of one of her husband’s extramarital affairs, Mr. Epstein suggested to Mr. Black that he separate from her “so he doesnt have a heart attack,” as Mr. Epstein put it in an email to Mr. Karp.
The Blacks remain married. Mr. Black’s lawyers said he never asked Mr. Epstein for marital advice.
One of the other women with whom Mr. Black had a relationship was the yoga instructor. Mr. Epstein was involved in paying her.
The woman, who was originally from Siberia, had known Mr. Epstein since at least 2009, when she was in her late 20s. Emails indicate that Mr. Epstein tried to connect her to powerful men, including the then-Prince Andrew and a senior JPMorgan Chase executive, Jes Staley. (Mr. Staley has denied knowing her. A spokesman for Andrew Mountbatten-Windsor didn’t respond to a request for comment.)
In 2017, she reached out to Mr. Epstein after receiving $28,000 from him, not the $100,000 that Mr. Black had told her to expect. “I just wanted to ask if there was any misunderstanding,” she wrote. She added that she previously had been paid directly by Mr. Black and didn’t know how the “new system” would work.
After some back-and-forth, Mr. Epstein confirmed that the full amount was on its way. “Next week you will receive,” he wrote.
Mr. Wyden said in his letter that Mr. Black appeared to use Mr. Epstein “as a middleman, raising concerns of potential money laundering.”
Cocaine Rumors
Despite, or perhaps because of, their close relationship, tension had been building between Mr. Epstein and Mr. Black. In 2017, it boiled over.
Mr. Epstein had received about $170 million by then but complained that he was not getting the money or gratitude he deserved.
That spring, Mr. Epstein mentioned to Mr. Karp that a rumor was circulating that Mr. Black was using cocaine. Mr. Black soon learned what Mr. Epstein had said. He was furious.
In what Mr. Epstein later described as an “ugly meeting,” Mr. Black accused him of spreading the cocaine rumor because he was dissatisfied with his compensation. He said Mr. Epstein was “out of control.” In their statement to The Times, Mr. Black’s lawyers said, “Other than experimenting with drugs early in his life, Mr. Black has not used illegal substances in more than 40 years.”
The men continued to meet and do business over the next several months, but signs of a strain persisted. That summer, Mr. Epstein complained about incurring a steep financial loss while helping Mr. Black save millions of dollars in capital gains taxes on a complicated transaction involving a Giacometti statue and a Cézanne painting.
“Something is wrong,” Mr. Epstein wrote in a long, rambling email to Mr. Black in August 2017. “Im not sure what it is. But it is clearly not the normal you.” Mr. Epstein lamented that despite everything he had done for Mr. Black, he had “failed to even buy me lunch.”
Mr. Black did not appear to respond to the email.
Two months later, allegations about the movie producer Harvey Weinstein’s sexual misconduct were dominating headlines, and Mr. Epstein was viewing Mr. Black’s situations with women through that lens.
“We live in a world where men in power cannot be seen to be taking advantage of young (20s) women,” Mr. Epstein wrote in an email to Mr. Karp. He said that some of the ways Mr. Black was handling his affairs with women were “frought with danger” and “asking for trouble.”
Mr. Black and Mr. Epstein kept working together for at least another year. In the fall of 2018, Mr. Black asked Mr. Epstein to review his latest tax return. He invited Mr. Epstein to participate in a planned investment.
Mr. Black also pushed Mr. Epstein to repay $30 million he had borrowed from Mr. Black in connection with the art transaction. Mr. Epstein wired $10 million to one of Mr. Black’s companies but did not repay the rest.
On Nov. 5, 2018, assistants to Mr. Epstein and Mr. Black emailed about rescheduling a lunch the two men had planned.
After that, there do not appear to be records of the men communicating with each other, though Mr. Epstein on occasion received emails in which acquaintances shared gossip about Mr. Black.
Later that November, The Miami Herald began publishing a series of articles about Mr. Epstein. In July 2019, Mr. Epstein was arrested and charged with sex trafficking.
Mr. Black played down their ties. Speaking to investors that month, he described the extent of the work that Mr. Epstein had performed for him: “From time to time, Mr. Epstein has provided professional services to my family partnership and related family entities involving tax, estate-planning and philanthropic advice.”
Will Houp, Urvashi Uberoy and Jenny Vrentas contributed reporting. Susan C. Beachy contributed research.
Matthew Goldstein is a Times reporter who covers Wall Street and white-collar crime and housing issues.
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