William Cohan says Leon Black paid Jeffrey Epstein $158 million for tax and estate advice, and even after years of reporting he still does not fully believe that is what the money was for.
Every other rich Wall Street client with the same problem went to Sullivan & Cromwell, Paul Weiss or Wachtell. Black went to a board member of his own family foundation with no tax credentials, and Cohan says it worked.
"But we've created this class, a hubristic class of people. They're able to have anything they want in the world and will forever."
Cohan spent years at Lazard and JPMorgan covering private equity firms as an M&A banker before becoming a journalist, and has written a New York Times-bestselling shelf of Wall Street books, including "House of Cards" and "Power Failure," before turning to Leon Black, Apollo and the Jeffrey Epstein files for his latest.
I listened to the full interview so you can skip it. 40 minutes of audio, 13 minutes of reading.
Here are the 8 takeaways that matter.
👤 Guest: William D. Cohan, a former Lazard and JPMorgan M&A banker turned journalist, author of "Money to Burn: The Unvarnished Truth About Leon Black, Apollo, and the Rise of a New Wall Street"
🎙️ Host: Anthony Scaramucci, founder and managing partner of SkyBridge Capital and founder and chairman of the SALT investment conference
📰 Published: 10 September 2026
🔴 YouTube | 🟢 Spotify | 🟣 Apple Podcasts | ⏱️ 40 min | ✅ Time saved: 27 min
Key Takeaways
Leon Black paid Jeffrey Epstein $158 million for tax and estate advice, and Cohan still doesn't buy that's all it was for
Epstein's fix saved Black an estimated $2 billion in taxes by getting him to give up $400 million in disputed Apollo dividends
Apollo split its founders' shares specifically so the firm wouldn't look like Leon's alone
Black held about 93 million shares against 58 million each for Harris and Rowan, and used the larger stake to get his way
Cohan's honey-trap theory: men with no social ease in high school became easy targets once they had money
Wall Street's systemic risk has moved out of the regulated banks and into firms like Apollo, and nobody has stress-tested it
Apollo now manages about $1 trillion, $850 billion of it private credit against $150 billion of private equity
Leon Black's father jumped from the 44th floor of the Pan Am Building amid a tariff scandal, while Leon was at Harvard Business School
Michael Milken was paid $550 million in a single year at Drexel before pleading guilty to securities violations
Drexel collapsed into bankruptcy in 1990 after borrowing short and lending long, like every bank that fails
JPMorgan Chase is on pace for about $66 billion of net income this year, evidence risk migrated rather than vanished
Cohan calls Mark Rowan the most articulate person on Wall Street and Leon Black one of its most misunderstood
1. The Insulation Thesis
Scaramucci opened by asking Cohan what the title of his new book, "Money to Burn," was getting at.
The title came from Cohan's wife, who runs two publishing companies as part of Macmillan. Cohan said the two of them had been circling a Greek-mythology angle on Apollo's name before she landed on the phrase, which he thinks captures a generation of private-equity founders who got rich off a tax-code benefit for debt financing, plus timing and their own skill
Scaramucci framed it as a paradox of wealth, citing Leona Helmsley on "the little people" and F. Scott Fitzgerald on the rich thinking differently, and asked whether that was the book's real thread
Cohan agreed and broadened it into a claim about a whole class of people who face no consequences. "It seems that, you know, he who has the gold, the golden rule, he who has the gold rules."
The very rich have, in his description, "every rich person amenity you could possibly imagine" — jets, boats, homes — and, in his view, no accountability to go with it
His comparison point was Tom Wolfe's Bonfire of the Vanities. He said today's ultra-wealthy have perfected the insulation the novel described — "surrounded by people who are beholdened to them" and unlikely to hear when they're behaving badly
He was careful to separate the observation from an accusation. Cohan said he isn't suggesting anyone in the book broke the law, only that the country has created a class of people who answer to no one, "from the Oval Office down"
2. The Rosebud Chapter
Scaramucci asked about Eli Black, Leon's father, and how his downfall shaped Leon's ambition.
Leon Black comes from ten generations of Orthodox rabbis, Cohan said — including his own father, who practiced in the Five Towns on Long Island before deciding to become a businessman and earning his MBA at Columbia
Eli Black built a conglomerate out of a company that made paper caps for glass milk bottles. He ran Seal-Kap, then converted it into United Brands, whose biggest holding was United Fruit — the country's main banana importer — along with Baskin-Robbins, A&W Root Beer and Foster Grant Sunglasses. The family lived on Park Avenue with a weekend home in Westchester, and Eli worked in the Pan Am Building, now the MetLife Building
The scandal that ended his career involved tariffs, and it broke while Leon was a second-year student at Harvard Business School — a school he attended only because his father insisted, after Leon majored in philosophy at Dartmouth
Eli Black jumped from the 44th floor of the Pan Am Building onto Park Avenue, breaking the glass with his briefcase. "Somehow broke the panes of glass with his briefcase. I'm not exactly sure how that happened. Committed suicide amid a scandal, which I talk about in the book. And that's the so-called rose bud chapter."
The family's wealth was tied to United Brands stock, and it collapsed with the scandal. With his mother an artist, his aunt an art dealer and his sister a teacher, it fell to Leon — still at Harvard Business School — to rebuild the family's finances and reputation
Cohan said the episode became Black's driving force for the rest of his life, and that he has never fully processed it. Asked whether Black worked through the trauma, Cohan said people tend to bury this kind of pain rather than "get the help that we need"
3. The Succession Fight
Scaramucci compared Black, Josh Harris and Mark Rowan to a rock band that built something huge and couldn't hold it together, and asked why.
Apollo rose directly out of Drexel's collapse. Cohan said Black assembled the "merry band of people he wants from Drexel" to build a different kind of private-equity firm, calling Apollo itself a metaphor for rising from the ashes
It was Leon's firm from the start, and the ownership structure said so once Apollo went public. Black wanted to show a succession plan was in place, so he named Harris and Rowan co-founders even though, Cohan said, they technically weren't — and gave them roughly 58 million Apollo shares, enough to make them instant billionaires at the IPO. Black himself held about 93 million shares and used that stake to get his way whenever the other two disagreed
"Two out of the three of them had to agree on things for anything to happen." In practice, Cohan said, Black's larger stake as the firm's real founder settled most disputes
The firm's culture tolerated bad deals as the cost of doing business. Cohan said the three had an understanding that some deals would work and some wouldn't, and that it wasn't going to hurt anyone's career
The succession question surfaced around 2020, when Black turned 70 and wanted to retire. He wanted Rowan to succeed him, even though Rowan had stepped back after building Athene, the insurance business that became Apollo's engine for private credit. Harris wanted the job; Rowan played it cool; Black got his way
4. The $158 Million Fee
The conversation turned to Jeffrey Epstein, whom Cohan called central to the book's final act.
Black paid Epstein $158 million for what was billed as tax and estate work, and Cohan says even he doesn't buy that's what it was for. "158 million is an outrageous number for tax and estate advice"
Cohan said he tried to find a fact that would refute Black's account and could not: "I've not been able to find out anything that kind of refutes that." He believes the fee also covered help structuring the purchase of planes, boats and art in a tax-efficient way
The one concrete piece of work Cohan could confirm was real. Black faced a problem in his estate planning for his children that, left unfixed, would have cost him $2 billion in taxes. The white-shoe firms he tried first — Sullivan & Cromwell, Paul Weiss, Wachtell — couldn't solve it
Epstein, a board member of Black's family foundation with little substantive role there, offered to help and found a fix. The fix required what Cohan called "the miracle consideration" — Epstein got Black to give up roughly $400 million in disputed Apollo dividends, and in exchange the documents were redrafted in a way that avoided the $2 billion tax bill
Cohan, working through the mechanics live, said: "I'm not sure I'm explaining that right. I'm not sure I fully still understand it."
Cohan built the account from Epstein's unsealed files, Black himself and Black's estate lawyers, since the two other people who might know the full truth are unavailable — one dead, and Ghislaine Maxwell, in Cohan's words, "not speaking either." He estimated he drew on 3 million of the roughly 6 million pages of files
5. The Honey Trap
Scaramucci proposed a generational theory for why powerful men fell for Epstein, and Cohan tested it against his reporting.
Scaramucci's theory: men with no social charisma in high school were easy targets later. He asked whether someone with no swagger in high school would have been easy prey for Epstein once he had money. Cohan agreed
Cohan said he explores the idea directly in the book, around page 575, with someone who has specific views on it. "Leon was not a cool kid in high school and, you know, he was not one who I think, you know, you know, got the ladies, so to speak."
Once such a person becomes wealthy and powerful, Cohan believes, Epstein sensed which rich men might make use of his services. He was careful not to claim Black used those services himself, only that Black had affairs — including one with Guzel Ganieva that became public despite his hope it wouldn't — showing his willingness to step outside his marriage
His framing throughout was diagnostic rather than accusatory. "I am to observe it as the cautionary tale that it actually is"
6. Rowan's Private-Credit Bet
Scaramucci asked Cohan to talk about Wall Street more broadly, and Cohan pivoted to what he called the book's real subject: how Mark Rowan changed the industry.
Rowan built Athene, an annuity insurer, into the engine of Apollo's private-credit business. Apollo's roughly $1 trillion of assets under management now splits into $850 billion of private credit against $150 billion of private equity, the business the firm started with
Cohan connects that shift to bank regulation after 2008. Risk that used to sit on Wall Street banks' own balance sheets — the kind that produced the 2008 crisis he wrote about in "House of Cards" — has moved out of the regulated banks under Dodd-Frank and Federal Reserve rules, and into alternative managers: Blackstone, KKR, Apollo, Brookfield and Ares
The banks themselves are still extremely profitable. Cohan said JPMorgan Chase is on pace to earn about $66 billion in net income this year
He left the systemic-risk question open rather than answering it. Private credit has drawn growing concern over the last six months, Cohan said, and "it hasn't really blown up yet" — but he does not rule out that it eventually does
7. Drexel's Rise and Fall
Scaramucci asked for a few sentences on Drexel, the firm all three Apollo founders came from.
Drexel was the place everyone on Wall Street wanted to work, in Cohan's telling. Black and Rowan both turned down Goldman Sachs, and Harris left Blackstone for Apollo rather than the reverse. Cohan called the firm "complete and utter disruptors," comparable to what Apollo itself later became, though more quietly
Michael Milken was, in Cohan's words, a genius who also pleaded guilty to securities violations and went to prison. "So he was also a criminal since pardoned of course because everybody is a criminal is being pardoned by Trump these days." Milken created the junk-bond market and was paid $550 million in a single year, a figure Cohan called unheard of for an investment banker at the time
The firm failed for an ordinary reason. Despite Milken's insight, Drexel "borrowed short and lent long" like every bank that gets into trouble, and it filed for bankruptcy in 1990, sending Black, Rowan, Harris and others to found Apollo
8. Rowan and Black in Brief
Scaramucci closed with rapid-fire word-association questions about Apollo's two most prominent figures.
On Mark Rowan: "Probably the most articulate. I mean, I've known Mark for 30 years because when I started at Lazard, one of my thankless tasks was to cover the private equity firms as an M&A banker." Cohan said private-equity dealmakers resented that role, since it meant potentially owing him fees for ideas they'd rather keep in-house. He has watched Rowan "evolve and emerge as a powerhouse on Wall Street" since
On Leon Black: "One of the most misunderstood people on Wall Street."
Cohan pointed to a Business Week cover that used one word to describe Black — ruthless — and said Black cultivated that image himself, even though he is also, in Cohan's account, a tough negotiator, a serious art collector with one of the finest private collections, and the author of what Cohan called an astounding philosophy thesis at Dartmouth
Cohan's own assessment turns darker by the end: brilliant and deeply flawed, undone by his ties to Epstein and to Ganieva, and ultimately forced to leave the firm he founded
Bonus Insights
A personal story opened the interview. Scaramucci revealed that Cohan's wife is the daughter of his middle-school librarian, who used to save the Sports Illustrated swimsuit issues for him in the school archive: "Mrs. Futter, do you have my stash?"
Scaramucci tied the book's theme to Citizens United, as his own aside rather than Cohan's argument. He said campaign-finance rulings let wealthy donors buy the same freedom from accountability the book describes, calling recent legislation something that "hurts the little guy" while protecting people like Apollo's founders
A slang test drew a two-word answer. Scaramucci asked whether Cohan knew what the RZ was, to check for a generational gap between them; Cohan answered simply, "The charisma."
Cohan's bottom line is that Leon Black's wealth bought him nearly unlimited insulation from consequence, and that the same forces — inherited trauma, financial engineering and an absence of accountability — explain both how Apollo was built and how it nearly came apart.
Products, Companies & Tools Mentioned
Apollo Global Management (The private-equity and private-credit firm Black, Harris and Rowan founded out of Drexel's collapse; now roughly $1 trillion in assets, $850 billion of it private credit)
Athene (The annuity insurer Rowan built, which Cohan says became Apollo's engine for private credit)
Drexel Burnham Lambert (Where Black, Rowan and Harris worked before founding Apollo; collapsed into bankruptcy in 1990 after Michael Milken's securities convictions)
Blackstone, KKR, Brookfield and Ares Management (The other alternative-asset managers Cohan says have absorbed risk that used to sit on regulated bank balance sheets)
JPMorgan Chase (Cited for its roughly $66 billion in expected net income this year, evidence banks stayed highly profitable even as risk moved to private funds)
United Brands and United Fruit Company (The conglomerate Eli Black, Leon's father, built around the country's main banana importer, along with Baskin-Robbins, A&W Root Beer and Foster Grant Sunglasses)
Lazard (Where Cohan worked as an M&A banker covering private-equity firms, including a young Mark Rowan)
SkyBridge Capital (Scaramucci's investment firm)
Books & Resources Mentioned
Money to Burn: The Unvarnished Truth About Leon Black, Apollo, and the Rise of a New Wall Street – William D. Cohan (The book this interview promotes, on Leon Black, Apollo and the private-equity boom)
House of Cards – William D. Cohan (Cohan's book on Bear Stearns' collapse in the 2008 financial crisis, referenced for its account of risk inside Wall Street banks)
Power Failure – William D. Cohan (Cohan's history of General Electric, named as his most recent book before this one)
The Bonfire of the Vanities – Tom Wolfe (Cited by Cohan as a novel about insulation that anticipated today's ultra-wealthy)
All the Wrong Moves – Anthony Scaramucci (Scaramucci's own forthcoming book, mentioned in the episode's close)
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