Jeffrey Epstein had advice for the Eastern European model who was establishing herself in New York.
“its time you start an education,” he wrote to her in 2010, according to a trove of files released by the US Department of Justice. “you are 22, –only ask questions of men. they are not really intersted in your opinions until you are 30. and then only marginally.”
Their frequent messages soon petered out, according to the government files, and it isn’t clear how their contact began or what it brought her, if anything. But within a couple of years, she appeared in the orbit of one of Wall Street’s wealthiest and most influential men: Leon Black, the co-founder of Apollo Global Management. He would hire her as a broker for art deals and shower her with more than $US1.7 million ($2.4 million) in cash, later labelled as gifts. When the IRS audited her, she relied on Epstein for help to prepare responses, including to an IRS request to interview her about the nature of her relationship with the billionaire.
Epstein later bragged about coming to Black’s rescue. “He has been kept safe to date ONLY as a result of my maniacal devotion to friends,” he wrote to Black’s longtime lawyer, Brad Karp. Her “interview was cancelled AFTER it was on the official request”.
The Justice Department’s largest release yet of the Epstein files shows he was Black’s stealthy do-it-all fixer. Beyond mere estate planning, the convicted sex offender arranged family portraits, helped the billionaire leverage a vast art collection, dug into Black’s investment in the storied publishing house Phaidon and obscured some of his most sensitive secrets.
When another woman, Black’s former mistress Guzel Ganieva, demanded $US100 million from the private equity titan in 2015, Epstein helped arrange sit-down meetings between the two and recommended having her surveilled. Black secretly recorded her at Le Bernardin, a power restaurant in New York’s Midtown, where he nudged her to reach a deal and warned that making any “frivolous” accusations in public would probably land her in jail.
Such scenes are part of the thousands of documents about Black in the Justice Department’s files. They show how Epstein – once invited by a publicist to an early screening of Michael Clayton, a movie about a stealthy fixer catering to high-level executives – ended up living that life with the famed investor.
Black, 74, has acknowledged paying Epstein $US158 million over the years, saying it was for advice on estate and tax planning. But the newly released documents show, often in Epstein’s own words, how enmeshed he was in Black’s financial and personal lives.
Representatives for Black had no comment. A lawyer for the former model said in a letter that she “is a bystander to these events”. The lawyer said the woman had only limited contact with Epstein and that any “reference to Epstein tarnishes my client even though she was not one of his ‘girls’.” Ganieva and Karp didn’t respond to messages.
A few days after Bloomberg contacted representatives for Black and the woman, the Justice Department removed almost every document identifying her from its website. What’s left are versions of records that black out her name and key details. Bloomberg, which has copies of the original postings, is omitting her name while seeking to understand the reasons for the potential new redactions. The Justice Department declined to comment on why references to her have disappeared.
While much of the Epstein files are grim, suggestive or obscene, many others capture routine conversations and business dealings. The women they include span victims, colleagues, associates and even bystanders.
In Epstein’s world, few billionaires loomed as large as Black. After working at the side of junk-bond king Michael Milken through the 1980s, Black set up Apollo and helped reshape Wall Street investing by seeking out opportunities in the financial catastrophes of others, building his firm’s image as a ruthless negotiator. His standing landed him on the boards of Dartmouth College and the Museum of Modern Art, where he was chairman.
The Justice Department’s documents show Epstein positioned himself as a friend, arranging to meet with Black’s young-adult children and to have their portraits painted. Epstein enjoyed unfiltered insight into his client’s wealth, such as an analysis of his finances. Their contact, sometimes daily, ranged from mundane to intense – wrangling colleagues, minimising taxes, criticising strategy and firing off notes to Black’s assistant at Apollo.
‘He has been kept safe to date ONLY as a result of my maniacal devotion to friends.’
Jeffrey Epstein’s email boast to Leon Black’s lawyer
When it came to art, emails show Epstein weighing in on how to manage Black’s holdings, discussing appraisals, auctions and money he borrowed from Wall Street backed by parts of his collection. In the case of Phaidon, a glossy publishing imprint catering to the interests of Europe’s affluent, Epstein sketched ambitious plans for using its brand across industries.
And at times, Epstein corresponded with Apollo colleagues including Marc Rowan, the billionaire who’s now CEO, sometimes fielding Rowan’s calls and arranging in-person meetings. It went both ways: On one day, Epstein would demand through Black’s assistant that Apollo’s chief accounting officer be more responsive, on another Epstein would hear from an Apollo partner about catching up.
“Neither Marc Rowan nor anyone else at Apollo (excluding Mr Black) had either a business or personal relationship with Jeffrey Epstein,” said Steve Lipin, a spokesperson for Rowan. “While Epstein sought such a relationship, it was declined at every turn.”
After Epstein’s arrest in 2019 for sex trafficking, and his death that year in jail, the public’s interest in his past dealings kept mounting.
For Black, who stepped down as Apollo CEO in 2021, that’s now exposing some of the very issues he and Epstein apparently tried to hide.
‘Only ask questions of men’
The woman from Eastern Europe entered the picture early.
In 2009, Epstein finished a jail sentence in Florida after pleading guilty to a pair of state charges, including procuring a minor to engage in prostitution. The next April, according to the Justice Department’s files, he was trying to guide the model’s new life in New York.
The email that laid out what Epstein called her “education” mocked her upbringing and hopes.
He offered her help with travel and briefly loaned her an apartment. Once, he asked where she was, and she eventually wrote back to say that she had been out of town. “No problem,” Epstein replied. “But in the future, at least while you are staying in an apartment of mine, I’d appreciate a call back, the phone works outside of New York.”
When she sought to take a film class, he scolded her: “This is not interesting … it is academic, you need skill building – not theory of film.” And he sent a warning: “I do not want any misunderstandings. I am giving you my advice on school and acting, you have not asked me to pay these schools for you, and I am hesitant to do so …”
Their communications appear to have broken off at the end of May 2010, after Epstein accused her of breaching his trust.
A few years later, according to Justice Department documents, Black was sending the woman what her financial records would later describe as gifts about once or twice a month. A list for 2013, released as part of the government’s cache, showed more than $US600,000 of payments, generally between $US20,000 and $US40,000 apiece. In 2015, another list showed they topped $US1.1 million. It’s not clear what the money was for.
By then, she had gone into business as an art broker, and Black worked with her. She would end up involved as Phaidon expanded further into art.
‘Strawman structure’
Black’s purchase of Phaidon, the glossy publisher, in 2012 and its takeover of an online marketplace known as Artspace two years later were publicly portrayed as a way to make art more accessible to a larger audience.
But behind the scenes, Epstein was dreaming much bigger.
Weeks before Phaidon unveiled the Artspace deal in 2014, Epstein wrote to Black’s team, urging them to consider using the brand across a swath of industries. He rattled off ideas: Phaidon Film. Phaidon Media. Phaidon Internet. Phaidon Insurance. Phaidon Air – which, Epstein added, would mean a jet.
But for Epstein, Phaidon would become a source of frustration. The way its corporate structure plugged into Black’s holdings was sprawling and complex, soon expanding to almost 40 entities, ownership vehicles and partners, according to a diagram included in the Justice Department’s files. Though Epstein was offered a briefing on what accountants called its “strawman structure”, he would later complain that he was left out of the loop. Over time, he expressed concern that Black’s team was mishandling it.
‘[Anyone] that would attempt to blackmail a US businessman would immediately become in the 21st century, what they term vrag naroda [enemy of the people]’
The email Epstein drafted as a potential warning to Black’s former mistress
Epstein was blunt, urging Black to replace executives in his family office to ensure it wouldn’t miss opportunities. Emails show other members of Black’s team responding to Epstein’s demands for information, and Epstein grousing that he wasn’t getting paid fairly for the money he was saving, which he reckoned should be a 50 per cent split. At times, he demanded tens of millions of dollars for work including his attention to Phaidon.
In 2016, Phaidon attempted another step in its expansion, agreeing to pursue a partnership with a little-known start-up called Artace.
As part of that arrangement, a senior Phaidon executive helped the billionaire buy a minority stake in the venture, arranging for the model-turned-art broker to invest, too. When the IRS later audited her in 2017, Epstein set out to examine her finances – including her involvement in that venture – as he helped guide accountants on how to respond to the government.
The Justice Department’s documents show a team of professionals trying to figure out how to describe more than $US600,000 of gifts she had received. Another message, relayed by an accountant, noted that an IRS auditor wanted to discuss her “personal/business relationship” with Black.
Later that month, Epstein expressed alarm about her situation in an email to Black, calling it “emblematic” of warnings that kept going unheeded. “I have repeatedly told you that these girls all want to show how clever they are,” Epstein wrote. “They come from countries where taxes are rarely paid and on top of that, they have no experience with real rules, money or biz.”
The next month, one of Black’s investment vehicles agreed to pay her art brokerage a $US1.8 million commission for helping to sell a Paul Klee oil work called Was fehlt ihm? from its collection to a Geneva-based gallery. The fee amounted to 23 per cent of the $US7.8 million sale price.
It took months to sort out her US income taxes. Eventually, the audit wrapped up. And Phaidon’s intended partnership with Artace appeared to fizzle.
‘He MUST be more careful’
Epstein wasn’t the only figure paid to solve Black’s problems. For years, the Apollo executive was counselled by Brad Karp, the longtime chairman of the elite law firm Paul Weiss. (Karp stepped down from that role this month, saying his appearance in the Epstein documents had become a distraction.)
While emails show Epstein and Karp getting along, Epstein sometimes called the shots, sending him instructions and demands, or even scolding him. Epstein also vented.
In one note, in October 2017, he complained about the challenges of trying to handle Black’s dealings discreetly, blaming the billionaire’s office for being “sloppy and amateurish”.
Using Black’s executive assistant as a “go-between, is very silly and fraught with danger for a chairman of a public company”, Epstein wrote. And “having his mistress and family partnership appear on top of one another on the cap tables is asking for trouble”. (He didn’t name that person.)
Then, after complaining that Black owed him fees, Epstein noted: “He is well known and underestimates the risks of disclosure.” The email ends with a smiley face.
In December 2017, Epstein laid out what he called “suggestions for moving forward”.
Black’s assistant at Apollo, he said, “should not be involved with girls … no payments etc”, Black couldn’t take his wife to see Karp about “these issues again”, and Black had to settle with “the Calif girl … (can you imagine her leverage).” It’s unclear to whom Epstein was referring.
There was also a plea for more discretion: Black’s “office staff is supposed to track dollars in dollars out. He MUST be more careful … too many people … I have some ideas.” Karp wrote back to say he understood, and added his own smiley face.
‘Enemy of the people’
Epstein and Karp had also worked on another thorny issue, hiding Black’s relationship with Ganieva, his former mistress from Russia. After Epstein’s death in 2019, she and the billionaire would end up in court, where she accused Black of rape and abuse. He denied it, saying they had a consensual affair before she tried to extort and destroy him. Courts dismissed her claims, pointing to a confidentiality agreement she signed with Black, in which he agreed to pay her $US100,000 a month for years. Black sued her former lawyers in a case dismissed last year.
But before that, while Epstein was alive, a fragile peace held.
Weeks before Black and Ganieva met for lunch at Le Bernardin in 2015, Epstein sent himself an email. It reads as the script of a potential warning to her: “I’ve decided to help you. However I am very disappointed by the fact that you felt it necessary to threaten me.”
It goes on: “You should also know that I felt it necessary to contact some friends in FSB”, a reference to the Russian security agency that succeeded the KGB. “And I thought did not give them your name. They explained to me in no uncertain terms that especially now”, anyone “that would attempt to blackmail a US businessman would immediately become in the 21st century, what they term vrag naroda meant”.
The email offered a translation: “enemy of the people”. And enemies were “dealt with extremely harshly”.
The note offers $US50,000 per month for two years and visa help. “If you decide to stay in Moscow, it’s OK with me.”
Later, Epstein recommended having her surveilled by a private investigator from the firm Nardello. Karp, the lawyer, agreed: “Yes. Do we know where she stays while in town?” Epstein also suggested having someone from Nardello on hand when she met with Black, in case of a “malfunction”.
A spokesperson for that firm said the firm was retained by Black’s legal counsel “to provide investigative support”. During the engagement, “no one at Nardello had any contact or communication with Epstein whatsoever, nor did the firm know that Black’s counsel was sharing documents or other work product with Epstein”.
The lunch at Le Bernardin opened with small talk, according to a transcript prepared by Nardello and included in the Justice Department files. Another rich man once asked for Ganieva’s hand in marriage at the beloved French restaurant, she explained, but she turned him down. “I chose you,” she told Black. They ordered, discussed the opera and art market, then they got down to business.
“You’ve told me that you’ve suffered a lot. And as someone I care about, and as someone that I’ve always respected, I’m sorry you’ve suffered,” he told her, adding, “I don’t believe I’ve had much to do with your suffering.”
Ganieva told him she wouldn’t agree to less than $US100 million. “For me, it was like a marriage,” she said. “I gave you seven years of my life.”
They went back and forth, with Black sketching out ways they could deal with her demands quietly or destructively. Eventually, he suggested that going public would be worse for her than for him: “It’s a hurtful path for me that you would take,” he said. “It’s going to be a disastrous path for you.” She left.
Mutually assured destruction
Days later, the pair met at The Modern, according to another transcript. That time, after pleasantries, Black offered an analogy to the US and Soviet Union avoiding World War III through a nuclear doctrine known as Mutually Assured Destruction. “OK,” she said. Both chuckled.
Each knew they could hurt the other, he said, eventually suggesting he set up a trust for her. He promised to provide details soon.
Black and the former mistress met again in October 2015 at the King Cole bar to firm up a multimillion-dollar deal.
“We both know I’ve treated you very well,” Black told her. “I will do what’s right in terms of getting you some financial security for a long time.” Then she asked for even more.
“Because you love me. And you care,” she explained.
“I do care,” he said. “But not that much.”
Bloomberg
The Business Briefing newsletter delivers major stories, exclusive coverage and expert opinion. Sign up to get it every weekday morning.
