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 knew • Marc Rowan, the $16 million that bought Athene, and why he put it on Apollo's balance sheet instead of in a fund • How an annuity company turns into a private credit machine, and why it is "not that much different than a bank" • "What if Marc's wrong?" and whether this could be a Bear or Lehman moment • Epstein, the $158 million, three lawsuits, and the first two paragraphs of Leon Black's legacy About the guest: William D. Cohan is a founding partner of Puck, where he writes about Wall Street, and a former investment banker who spent 17 years at Lazard Frères, Merrill Lynch and JPMorgan Chase. He is the author of eight books, including The Last Tycoons (Lazard), House of Cards (Bear Stearns), Money and Power (Goldman Sachs) and Power Failure (GE), which he discussed on his first appearance on this show. His latest, Money to Burn: The Unvarnished Truth About Leon Black, Apollo, and the Rise of a New Wall Street, was published by Portfolio in September 2026. Links: Money to Burn: Amazon | Bookshop Bill Cohan at Puck: https://puck.news Bill Cohan on X: @WilliamCohan Bill’s first appearance on The World According to Boyar Boyar Research on Substack: https://boyarresearch.substack.com Memorable moments: “He said, well, basically, we don’t think you’re smart enough and we don’t think you have the personality and what it takes to be an investment banker. He was wrong.” (6:04, Cohan; the last two words are Jonathan’s) “They knew the credits because they had basically sold all that debt at par to investors and now was trading at 30 cents or 50 cents or whatever.” (21:51, Cohan) “So it’s all a confidence game, Jonathan. Nothing has really changed other than so far, it’s working and so far, he’s meeting his obligations and so far, the confidence remains and so far, we haven’t had a credit crunch since 2008.” (about 43:10, Cohan) Disclosure: This podcast is for informational and educational purposes only and should not be considered investment advice, a recommendation to buy or sell any security, or an offer to provide investment advisory services. The views expressed by guests are their own and do not necessarily reflect the views of Boyar Research or its affiliates. Boyar Research, its affiliates, employees, and accounts managed by its affiliates may own shares of companies mentioned in this episode. Our views are subject to change at any time, and we are under no obligation to update listeners if our opinions or positions change. Investing involves risk, including the possible loss of principal. Listeners should do their own research and consult with their own financial, tax, or legal advisors before making any investment decisions. The Boyar Value Group: Uncovering Investment Opportunities Since 1975 Founded in 1975, The Boyar Value Group has spent more than five decades seeking to uncover undervalued opportunities in the stock market. Through Boyar Research, we provide in-depth, independent research focused on businesses we believe are misunderstood, underfollowed, or trading at a meaningful discount to intrinsic value. Our investment management business applies that same research-driven discipline to manage portfolios for both institutions and individuals, utilizing our private equity approach to stock market investing. To learn more about The Boyar Value Group, please visit www.boyarvaluegroup.com. Never miss another Boyar podcast, market insight, or other valuable content — subscribe to our Substack at boyarresearch.substack.com. Disclosure This podcast is for informational and educational purposes only and should not be considered investment advice, a recommendation to buy or sell any security, or an offer to provide investment advisory services. The views expressed by guests are their own and do not necessarily reflect the views of Boyar Research or its affiliates. Boyar Research, its affiliates, employees, and accounts managed by its affiliates may own shares of companies mentioned in this episode. Our vi...
