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Money, Hubris and Jeffrey Epstein: The Fall of Leon Black, w/ William Cohan

On with Kara Swisher

Hosted by Kara Swisher

56m
Transcript

Original podcast

Summary

Written by a model from the transcript; not yet reviewed.

Journalist and author William Cohan joins the podcast to discuss his new book, Money to Burn, which chronicles the rise and fall of billionaire Leon Black and his private equity firm, Apollo. Cohan explains how Black innovated by buying distressed debt rather than just equity, but details how his career unraveled due to his extensive financial ties to convicted sex offender Jeffrey Epstein and an expensive extramarital scandal. The conversation also explores the broader landscape of modern Wall Street, including the explosive growth of private credit, massive speculative bets on artificial intelligence, and mounting warning signs in the bond and trade markets.

The discussion further examines the risks embedded in private credit firms like Apollo, which fund their lending through insurance annuities rather than traditional bank deposits. Cohan and the host analyze recent major corporate news, including Meta's 17-billion-dollar settlement over teen social media addiction and escalating tariff threats involving Canada. Featuring an expert question from Bethany McLean on alternative finance models, the episode offers a clear-eyed look at the unchecked risk-taking that defines modern high finance and its potential consequences for everyday Americans.

  • Understand that Drexel pioneered the use of highly confident letters to give raiders like Carl Icahn unbacked leverage for massive corporate takeovers. 11:30
  • Recognize that modern private credit giants generate long-term investment capital by selling fixed-rate annuities through captive insurance companies like Athene. 14:12
  • Remember that market corrections are ultimately triggered not by predictable catalysts, but by a sudden, systemic loss of investor confidence. 41:32

Chapters

  1. 0:31
    Podcast Intro and Host Overview

    Kara Swisher introduces the episode, hosts, and the focus on Leon Black’s story.

  2. 2:13
    Black’s Early Life and Family Turmoil

    Explores Black’s upbringing, his father’s death, and the financial pressures that led him to finance.

  3. 7:05
    The Epstein Connection and Black’s Justifications

    Examines Black’s relationship with Jeffrey Epstein, the $158 million payments, and his rationalizations for continuing the ties.

  4. 10:00
    Apollo’s Transformation into Private Credit

    Describes Apollo’s shift under Mark Rowan, the creation of Athene, and the rise of private credit as a new Wall Street model.

  5. 19:40
    Impact on Black’s Reputation and Corporate Roles

    Discusses Black’s resignation, ongoing board positions, and the lingering Epstein scandal’s effect on his public image.

  6. 39:09
    Broader Wall Street Trends: AI and Valuation Bubbles

    Kara and William analyze the AI boom, valuation concerns, and potential market corrections.

  7. 49:40
    Introduction and Guest Arrival

    Kara Swisher welcomes journalist Bethany McLean and introduces the episode’s focus on Leon Black’s Apollo and the Athene insurance saga.

  8. 50:16
    Mark Walter and the Guggenheim Empire

    Explanation of Mark Walter’s role, his ownership of the Dodgers, insurance ventures, and the broader Guggenheim conglomerate.

  9. 52:21
    Private Credit’s Appetite for Risk

    Exploration of how Apollo and similar private credit firms have reshaped Wall Street’s risk tolerance and its societal impact.

  10. 53:49
    Closing Reflections and Takeaways

    Kara summarizes key insights, praises the book, and encourages listeners to engage further with the content.

  11. 54:57
    Production Credits and Final Notes

    Acknowledgment of the production team, sponsors, and a brief wrap‑up of the episode’s conclusion.

Highlights

  • 4:05

    Apollo's Distressed Debt Strategystrategy

    William Cohan explains how Apollo stood out from traditional private equity by buying distressed bonds and converting them into controlling equity during corporate bankruptcies.

  • 14:47

    The Private Credit Insurance Modelinsight

    The guest breaks down how Apollo bypasses traditional bank deposits by using retail annuity money from its insurance arm to finance long-term private loans.

  • 22:49

    The Deckard Report Findingsdata

    Cohan discusses the internal report commissioned by Apollo which revealed that Leon Black paid Jeffrey Epstein 158 million dollars for tax and estate advice.

  • 39:48

    AI Valuation Bubble Concernsinsight

    The speaker characterizes current market enthusiasm for artificial intelligence and upcoming tech public offerings as a valuation bubble of epic proportions.

  • 44:03

    Meta Teen Addiction Settlementstory

    The host and guest analyze Meta's decision to settle teen social media addiction litigation for 17 billion dollars, concluding the company simply faced certain defeat.

  • 49:10

    Exploding National Debt Costsdata

    William Cohan points out that the United States now spends over a trillion dollars annually on interest payments, surpassing total military spending.

  • 50:07

    Comparing Private Credit Modelsdebate

    Journalist Bethany McLean asks whether competitor Mark Walter's empire is a cruder version of Apollo's annuity-backed lending model, raising systemic risks.

Quotes

  • “Apollo was always set up to be in a position to buy other parts of the capital structure and not just the equity.”
    Unnamed speaker · 4:05
  • “The Deckard Report did not find any wrongdoing, but it found that he paid him $158 million.”
    Unnamed speaker · 22:49
  • “Ken Griffin. He's the wealthiest guy on Wall Street. He's even wealthier than Schwartzman. He's buying up all of Florida, half of Manhattan.”
    Unnamed speaker · 53:57
  • “Mark Rowan would say, we are investing our private capital dollars in senior secured debt.”
    Unnamed speaker · 52:53
  • “Silicon Valley Bank invested in treasury securities. They still went out of business and were liquidated because there was a run on the bank.”
    Unnamed speaker · 53:30
  • “you can't liquidate them to meet the redemption demand, so what?”
    Unnamed speaker · 53:44
  • Lululemon 2:13–2:38
  • Lululemon 19:14–19:31
  • Lululemon 38:52–39:09
  • Lululemon 55:39–56:06

About this episode

In his new book, “Money To Burn,” author and Puck journalist William Cohan traces the rise and fall of one of Wall Street’s most towering modern figures: billionaire Leon Black. His private equity and investment firm, Apollo, changed Wall Street, making Black enormously rich. He reached the highest rungs of New York society, but his ties to convicted sex criminal Jeffrey Epstein ultimately took him down. Kara and Bill talk about how Black and Apollo ushered in a "new Wall Street" and the nature of Black's relationship with Epstein, which continued for almost a decade after Epstein's 2008 conviction for soliciting prostitution from a minor. They also break down some of the latest headlines in business and finance, including Meta’s $17 billion settlement and President Trump’s escalating trade war with Canada. Questions? Comments? Email us at [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

0:00
56:54

10,131 words · 5 speakers

Speaker names marked are inferred from speaking time and the show’s known hosts — they are not voice-verified.

Topics

  • Apollo
  • Drexel
  • Athene
  • SpaceX
  • Nvidia
  • Meta
  • Anthropic
  • KKR
  • Brookfield
  • TPG

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