Wall Street journalist William D. Cohan — author of the New York Times bestseller Money to Burn, on Leon Black and the rise of Apollo — joins the Chuck ToddCast to connect the dots between media consolidation, private equity, and the opaque corner of finance the ToddCast has been chasing since the Lakers special report. Cohan explains why Skydance needs CNN’s cash flow to service $80 billion in debt, why Trump may kill Nexstar’s bid for ABC out of spite toward Disney, and how a sports franchise purchase actually gets financed — including whether Mark Walter bought the Dodgers or insurance premiums did. On Black, Cohan had extensive access: Black maintains the hundreds of millions he paid Epstein were for tax and estate planning, and an investigation he commissioned found no nefarious activity, though Cohan is skeptical anyone pays that much for tax advice. His closing warning echoes Chuck’s: after 2008 regulators pushed risky assets outside the banks, and the new shadow banking system is barely regulated at all. 

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Timeline:

00:00 William D. Cohan joins the Chuck ToddCast

02:30 Will public companies offload their news networks?

04:15 Skydance’s $80 billion debt and why it needs CNN

08:15 Nexstar, ABC, and Trump’s grudge against Disney

12:15 Netflix, YouTube, Apple, and who’s actually winning

17:45 Redbird, overinflated valuations, and the Lakers money

24:30 Trophy purchases, the Dodgers, and insurance premiums

29:00 Private equity as a business — and as a political boogeyman

36:30 Bessent as sycophant, and the treasury buyback

38:30 Leon Black, Epstein, and an attempted rehabilitation

45:00 Shadow banking and the crisis we’ll regulate afterward