Episode Details

Bill Cohan, author of Money to Burn, on how Leon Black built Apollo out of the wreckage of Drexel Burnham and whether the annuity company at the heart of Apollo today could be at the center of the next financial crisis. 

Bill Cohan is one of my favorite business writers, and this is his second time on the show. His new book, Money to Burn, is the story of Leon Black and Apollo, and it covers a lot of ground: the big deals, the $158 million paid to Jeffrey Epstein, the fall from the top of the firm. What grabbed me was the origin story, so that is where we spend most of our time. 

Leon Black did not want to go to Wall Street. When he tried, Lehman Brothers turned him down after four rounds of interviews and told him, in Bill's telling, "we don't think you're smart enough." To say they were wrong is a dramatic understatement. He went to Drexel Burnham instead, became the fastest partner in the firm's history, and invented the highly confident letter, a piece of paper with no legal force that let corporate raiders bid for companies they could not afford. When Drexel collapsed in February 1990, Black took the best people he could corral, got a French state-owned bank to put up $800 million, and started buying, at a steep discount, the very bonds Drexel had sold at par. Bill explains why that was the edge: "They knew the credits because they had basically sold all that debt at par to investors." The Executive Life deal, a $6 billion junk-bond portfolio bought for about $3 billion, made Apollo, and it also produced a scandal that led to indictments, a huge fine, and sealed records that Bill still couldn’t get his hands on. We talk about what Leon knew.

The second half is about Athene, the annuity company Marc Rowan backed with a $16 million check and that now sits at the center of Apollo. Bill walks through how it works in plain English: take retirees' savings, promise them 5 or 6 percent, lock the money up for seven to ten years, and invest it in loans that yield more. I asked whether that is different from what the banks were doing with mortgage-backed securities before 2008. His answer: "That's right, Jonathan. That's why, you know, to some extent, some people, including me to a certain extent, think that this is deja vu all over again." We get into what happens if Marc is wrong, why Bill does not think it is a Bear or Lehman moment, and the Medallia deal, which he calls a canary in the coal mine for private credit .

We close with Epstein, the lawsuits (the women who sued him are "O for 3," in Bill's phrase, and Leon has prevailed), and the question I always ask about a career like this: what will the first two paragraphs of the obituary say? 
Buy the book: Money to Burn: The Unvarnished Truth About Leon Black, Apollo, and the Rise of a New Wall Street (Portfolio, 2026). Amazon I Bookshop I Barnes & Noble 

What we cover:

 
• Why the book opens with Eli Black (Leon's father), an Orthodox rabbi turned corporate raider, jumping through a window of the Pan Am Building
• The Lehman rejection: "we don't think you're smart enough," and how wrong that was
• What Drexel Burnham was, for listeners too young to remember, and why Milken
"put the fear of God into corporations"
• The highly confident letter: "smoke and mirrors, but it was highly effective," and raiders paid real money for it
• Why Mike Milken would not talk to Bill, and why his indictment cannot be found on the internet
• Milken's $550 million year, and what Wall Street would look like if Drexel had survived to 2008
• The inside advantage: buying bonds Drexel had sold at par, now trading at 30 or 50 cents
• Gillett Holdings and Vail: taking over a company Leon had advised to be built
• Executive Life: a $6 billion junk-bond portfolio for 50 cents on the dollar
• The Credit Lyonnais shell companies, the indictments, and the question of what Leon k