Jeffrey Epstein’s Angry Emails to Billionaire Leon Black

Jeffrey Epstein was furious. For years, he had relied on the billionaire Leon Black as his primary source of income, advising him on everything from taxes to his world-class art collection. But by 2016, Mr. Black seemed to be reluctant to keep paying him tens of millions of dollars a year.

So Mr. Epstein threw a tantrum.

One of Mr. Black’s other financial advisers had created “a really dangerous mess,” Mr. Epstein wrote in an email to Mr. Black. Another was “a waste of money and space.” He even attacked Mr. Black’s children as “retarded” for supposedly making a mess of his estate.

The typo-strewn tirade was one of dozens of previously unreported emails reviewed by The New York Times in which Mr. Epstein hectored Mr. Black, at times demanding tens of millions of dollars beyond the $150 million he had already been paid.

The pressure campaign appeared to work. Mr. Black, who for decades was one of the richest and highest-profile figures on Wall Street, continued to fork over tens of millions of dollars in fees and loans, albeit less than Mr. Epstein had been seeking.

Of all the relationships that Mr. Epstein built with the rich and powerful, his friendship with Mr. Black was arguably the most important. After Mr. Epstein served jail time for soliciting prostitution from a minor, many of his contacts backed away. Not Mr. Black, who kept Mr. Epstein afloat for years.

The new emails, along with court documents and interviews, provide the most complete picture yet of that relationship. They come at a time of renewed interest in Mr. Epstein, stoked by the Trump administration’s refusal to release government records related to investigations into him. The president, who was once friends with Mr. Epstein, has sought to deflect attention onto “hedge fund guys” and other prominent men who he says were much closer to the predator than he once was.

Mr. Black, 74, was pushed out of the private equity firm he co-founded, Apollo Global Management, in 2021 over his ties to Mr. Epstein. He has said that his payments to the sex offender were simply for tax- and estate-planning services. Those claims have puzzled many on Wall Street, who have asked why one of the country’s richest men would pay Mr. Epstein, a college dropout, so much more than what prestigious law firms would charge for similar services.

The two men had been personally entwined for more than two decades. When a former girlfriend accused Mr. Black of sexual assault, he turned to Mr. Epstein for advice about paying her millions of dollars to keep it quiet, according to an email reviewed by The Times and court records. Another woman said in a lawsuit that Mr. Black had raped her at Mr. Epstein’s Manhattan townhouse. She eventually dropped the lawsuit.

And, for reasons that are unknown, Mr. Black wired hundreds of thousands of dollars to at least three women who were associated with Mr. Epstein, according to court documents and notes taken by congressional investigators that were shared with The Times.

Representatives of Mr. Black did not respond to questions about those payments to women.

Susan Estrich, a lawyer for Mr. Black, said his payments to Mr. Epstein were for tax- and estate-planning services that an outside law firm found were legitimate.

“To imply that Epstein somehow had influence over Mr. Black is false and patently absurd,” she said. She added that the law firm, hired by Apollo to review the men’s relationship, 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.” Mr. Black has said he regretted working with Mr. Epstein.

The emails reviewed by The Times — sent in 2015 and 2016 to Mr. Black through his personal assistant, as well as to a handful of his advisers — show another dimension of Mr. Epstein’s cruelty. While he was known for ingratiating himself with the rich and powerful, he could also veer into nastiness and was willing to turn the screws on his biggest client. (None of the emails reviewed by The Times were written by Mr. Black.)

“I will no longer, not even for one day, work on your affairs. without the compensation that is long overdue,” Mr. Epstein wrote in November 2015. Mr. Epstein demanded “the usual 40 million per year,” with most of it paid upfront.

Months later, as their fight over payments roared on, Mr. Epstein offered a concession: “Of course re any non financial issues, I am always there for you and will continue to be the best friend I can be.”

‘Love and Kisses’

Mr. Black and Mr. Epstein met thanks to Mr. Epstein’s knack for inserting himself into other people’s business.

One morning in 1994, Mr. Epstein called his friend Elliot Stein and invited him to lunch. Mr. Stein replied that he already had plans: He was meeting Mr. Black at the China Grill in Midtown Manhattan.

Mr. Epstein invited himself along, Mr. Stein recalled, and spent the meal chatting with Mr. Black about markets and trading.

Soon Mr. Epstein cultivated Mr. Black as his own friend. Later that year, after Mr. Epstein canceled a dinner with Mr. Black and his wife, he asked an employee to send them chocolates with an apology, according to notes taken by the employee.

The two men had a lot in common, sharing interests in science, art and finance.

Mr. Black had co-founded Apollo in 1990. The firm, which was a trendsetter in using debt to buy distressed companies, became a powerful force on Wall Street.

Mr. Epstein had no formal training in tax and estate planning. But after a few years working at an investment bank, he convinced a few business elites to hire him for financial advice. They included Elizabeth Johnson, an heiress to the Johnson & Johnson fortune, and Leslie Wexner, the billionaire behind Victoria’s Secret and the Limited.

Mr. Black found Mr. Epstein to be impressive and a little mysterious. It wasn’t just his ties to the ultrawealthy; he also seemed to always be surrounded by beautiful women. “He was almost like a James Bond villain,” Mr. Black told the publication Puck last year.

In 1997, long before Mr. Epstein became a formal adviser to Mr. Black, he and his wife, Debra, put Mr. Epstein on the board of directors of their newly created family foundation. A couple of years later, Mr. Black and two other Apollo executives together donated $500,000 to one of Mr. Epstein’s nonprofits, which gave money to charities.

Mr. Epstein introduced Mr. Black to several young women, according to people familiar with their relationships, as well as court documents. Some of the women later accused Mr. Black of abusing them.

In 2002, for example, Mr. Epstein arranged for Mr. Black to meet Cheri Pierson, whom Mr. Epstein had paid for massages, according to a lawsuit Ms. Pierson filed years later and eventually withdrew. She met Mr. Black at Mr. Epstein’s townhouse, where Mr. Black raped her in the massage room, the lawsuit said. Mr. Black denied the claim and said he had never met Ms. Pierson.

In early 2003, Mr. Black was among the friends who contributed to a book celebrating Mr. Epstein’s 50th birthday. Mr. Black’s entry, a handwritten poem, referred to Mr. Epstein’s “unique tax strategy” and his interest in women: “Blonde, Red or Brunette, spread out geographically / With this net of fish, Jeff’s now ‘The Old Man and the Sea.’”

A few years later, a Florida grand jury indicted Mr. Epstein for soliciting prostitution from a teenager. Mr. Black later said the felony charge against Mr. Epstein — which resulted in him serving 13 months in jail — didn’t seem like a big deal at the time.

“I mean, he was with a 17-year-old prostitute, got prosecuted for it and got put away for a year,” Mr. Black told Puck. “I didn’t think this was the end of the world, frankly.”

Dodging Taxes

In 2011, Mr. Epstein was at a crossroads. He was a registered sex offender, and his main benefactor — Mr. Wexner, the retail billionaire — had long since cut ties. His personal investments, while sizable, had plummeted since the 2008 financial crisis, according to records filed by one of Mr. Epstein’s companies.

And his opulent lifestyle and sex-trafficking operation continued to rack up expenses. He needed a new source of revenue.

Mr. Black, too, was at a crossroads of sorts. Apollo had gone public in 2011, and Mr. Black’s personal wealth had soared. He was looking for help managing his fortune and shielding it from taxes.

Mr. Epstein seemed to fit the bill. He began advising Mr. Black on a wide variety of matters, including taxes, estate planning, investments, charitable giving and the operation of his family yacht. When Mr. Black traveled to Russia for a meeting of a state investment board, Mr. Epstein planned to go, too, according to a calendar entry kept by one of his assistants and a travel visa reviewed by The Times.

Mr. Epstein had found a new cash cow. In 2012, he received a $5.5 million payment from Mr. Black, which appears to have been the first transaction between the two men, according to the notes taken by congressional investigators. Months later, they signed a contract in which Mr. Black agreed to pay Mr. Epstein $23.5 million for “estate planning matters.”

Mr. Epstein sought to professionalize Mr. Black’s family investment office, which managed the billionaire’s assets. He constructed — and sometimes participated in — art transactions that were designed to skirt capital gains taxes and keep Mr. Black’s purchases from drawing public attention, according to emails reviewed by The Times.

He used his connections at JPMorgan Chase — where Mr. Epstein was a prized client — to seek a loan for Mr. Black. In one email, he told a banker that he was advising on Mr. Black’s $120 million purchase of Edvard Munch’s painting “The Scream.”

Mr. Black’s representatives said Mr. Epstein was not involved in Mr. Black’s 2012 purchase of the painting.

Most important, he found ways to minimize the taxes that Mr. Black’s estate would owe after his death. Years earlier, at the suggestion of Mr. Epstein, Mr. Black had set up a so-called grantor-retained annuity trust. Such trusts allow the ultrawealthy to pass along potentially unlimited sums to their heirs, free of any estate tax. In 2013, Mr. Epstein came up with a way to rework the trust to potentially avoid hundreds of millions of dollars in taxes for Mr. Black’s four children.

And when the I.R.S. audited some of Mr. Black’s tax strategies, Mr. Epstein helped resolve the inquiries, according to the emails reviewed by The Times.

While Mr. Epstein repeatedly rattled off the projects he said he was undertaking for Mr. Black, the actual role that he played — as well as the true value derived from that work — is unclear.

Yet Mr. Epstein told Mr. Black that the work was highly valuable. Mr. Black generally coughed up the fees Mr. Epstein requested. The total would ultimately reach $170 million. By a wide margin, Mr. Black was Mr. Epstein’s greatest source of income after 2012. (The apparent runner-up: the French banker Ariane de Rothschild, who paid Mr. Epstein at least $15 million in 2015.)

Mr. Epstein also gave Mr. Black access to his Rolodex. Over the years, he connected him with Bill Gates and Stephen K. Bannon. He introduced one of Mr. Black’s sons to Woody Allen to learn about film editing, according to court records. Mr. Black, meanwhile, donated millions to one of Mr. Epstein’s charities.

Some work that Mr. Epstein performed for Mr. Black required the utmost discretion. For instance, he helped him keep a long-running extramarital affair under wraps.

Mr. Black paid nearly $10 million to Guzel Ganieva, with whom he had a sexual relationship and who had accused him of assault. The agreement required Ms. Ganieva not to publicly disclose the relationship. (Mr. Black has acknowledged the affair but denied the assault allegation.) One of Mr. Epstein’s tasks was to look into whether the payments, some of which were structured as loans, would incur federal gift taxes, according to court filings and the emails The Times reviewed.

Pleading for Pay

By 2015, fissures were beginning to surface in the relationship between the two men. Mr. Epstein wanted more money. Mr. Black was balking.

The spat was captured in Mr. Epstein’s emails, written in a stream-of-consciousness manner with little regard for the conventions of grammar, punctuation or spelling. Mr. Epstein later compiled the emails with notes to himself about the role he had played in managing Mr. Black’s finances, apparently to help make the case that he deserved to be paid.

Mr. Epstein alternated between sounding angry, boastful and defensive.

He detailed the extensive work he had performed and how much money it had saved his client. He derided the employees in Mr. Black’s family office and one of the billionaire’s outside advisers at the elite law firm Paul Weiss.

The underlying message: Mr. Black could trust only Mr. Epstein, and he deserved to be paid accordingly.

Shortly after a meeting with Mr. Black and some of his advisers in November 2015, Mr. Epstein typed a long email that alluded to what he said were his long-running warnings about Mr. Black’s staff.

One adviser’s comments were “totally incomprehensible,” Mr. Epstein wrote, and “the charts he prepared unreadable.” Another adviser spent the meeting in a “defensive posture,” leading Mr. Epstein to wonder if he had felt “sandbagged” by Mr. Epstein’s presence.

Mr. Epstein went on to propose one final year of work. “I think you should pay the 25m that you did not for this year,” he wrote. “For next year its the same 40 m as always, paid 20 in jan and 20 in july, and then we are done.”

Over the course of 2016, Mr. Epstein ratcheted up the pressure to get paid.

“As you often like to remind me- you’ve paid a great deal of money to date,” he wrote that March. “That being said - If you want my involvement moving foward, I suggest you pay my regular I fee of 40 m.”

If cash was a problem, he offered, then Mr. Black could pay him in other ways, like by giving him Miami real estate or artwork, or financing his new plane.

Several weeks later, still frustrated, Mr. Epstein dashed off an email that explained the value he had provided Mr. Black over the years.

“If you reflect on your financial life, you have been kept safe, had remarkable results and no disasters,” he wrote.

But Mr. Black was putting his fortune at risk, Mr. Epstein warned. “I have repeatedly urged you to get rid of the people in your office,” he wrote. “You have repeatedly chosen to ignore my advice.” Mr. Black had complained about his high fees, he went on, while “ignoring the benefit of between 1.5 and 2b to the better,” a reference to how much Mr. Epstein claimed he had saved Mr. Black.

Six months later, in November 2016, the dispute was still simmering. Mr. Epstein said Mr. Black urgently needed to clean up the “procrastination produced mess” that was his estate — and that Mr. Black’s children had contributed to.

“You have a bomb of colored string that your retarded children have formed,” he wrote. “It has to be very carefully unwound.”

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.

That being said , the tasks at hand are the following. You have a bomb of colored string that your retarded children have formed , It has to be very carefully unwound ,

Ms. Estrich, the lawyer for Mr. Black, said he ultimately “fired Epstein because he was disruptive and believed the fees for his services were excessive.”

Even after the payments stopped, Mr. Black kept soliciting his friend’s advice.

In October 2018, one of Mr. Black’s advisers emailed Mr. Epstein to say that Mr. Black had requested that he provide a “high level review” of Mr. Black’s 1,700-page federal tax return.

Weeks later, Mr. Epstein’s criminal enterprise began to unravel.

A Virgin Islands Inquiry

In November 2018, The Miami Herald published a series of articles about Mr. Epstein’s sweetheart plea deal a decade earlier. The public outcry that followed led federal prosecutors to reopen investigations into his sex-trafficking operation. He was arrested in 2019 and died by suicide in a Manhattan jail cell.

Mr. Black initially played down his ties to the notorious predator, denying knowledge of his crimes and saying that top law firms had vetted his financial services. Mr. Black’s exalted position at Apollo and on Wall Street appeared secure.

After The Times reported in 2020 that Mr. Black had paid Mr. Epstein as much as $75 million, Apollo hired Dechert to get to the bottom of the matter. The firm concluded that Mr. Black’s payments to Mr. Epstein had been for legitimate tax- and estate-planning services. But its public report, while sparse on details, made clear that the relationship between the two men had been extensive.

That shook investor confidence in Apollo, and in early 2021, Mr. Black was pushed out of the firm he had helped create. He also agreed not to seek another term as chairman of the Museum of Modern Art in New York, a post he had long prized.

The next year, Senator Ron Wyden, Democrat of Oregon, began looking into Mr. Black’s payments to Mr. Epstein. Investigators learned that Bank of America, where Mr. Black had accounts, had flagged $170 million of his payments to Mr. Epstein as suspicious. They also discovered that Mr. Black had paid millions of dollars to eight women, according to the congressional notes shared with The Times.

At least three of those women were listed among Mr. Epstein’s associates and victims in federal court filings. Mr. Black’s representatives did not answer questions from The Times about why he had paid the women.

Authorities in the U.S. Virgin Islands, where some of Mr. Epstein’s businesses had been based and many of his sex crimes had taken place, opened their own investigation into Mr. Epstein’s financial partners, including Mr. Black.

Lawyers working for the territory’s attorney general interviewed at least two women who claimed they had been sexually abused by Mr. Black after Mr. Epstein introduced them, according to several people briefed on the matter and interview notes.

It is unclear whether the attorney general’s office substantiated those allegations. In 2023, Mr. Black agreed to pay the territory $62.5 million to end the investigation.

Whit Clay, a spokesman for Mr. Black, said at the time that the settlement did not involve any allegations of misconduct. He said it was simply to resolve claims arising from the “unintended consequences” of the fees that Mr. Black had paid Mr. Epstein.

Nicholas Confessore contributed reporting. Kirsten Noyes, Susan C. Beachy and Julie Tate contributed research.