Restructuring 101: How Private Equity Pits Debt Investors Against Each Other | Caesars Part 2/3 Artwork

The Wall Street Skinny

Where Bloomberg meets Page Six.

Join us -- Kristen and Jen -- two former Morgan Stanley and Lehman Brothers investment bankers who take the most complex deals, market moves, and stories in finance and distill them into what actually matters.

From conversations with the biggest names in investing to deep dives people can’t stop sharing (not to mention the occasional HBO Industry red carpet), this is the show Wall Street is obsessed with.

All Episodes

The Wall Street Skinny

Restructuring 101: How Private Equity Pits Debt Investors Against Each Other | Caesars Part 2/3

April 20, 2026 • Kristen and Jen

0:00 | 45:30

Send us Fan Mail

This is Part II of our Caesars Palace deep dive, and honestly, this is where things get truly unhinged. If Part I was the setup — the $30 billion LBO, the financial crisis, and the private equity firms scrambling to keep the lights on — this episode is the masterclass in what happens when the knives come out. We're breaking down the mechanics of distressed debt investing, restructuring, and bankruptcy. Above all, we'll explain how Apollo essentially invented a new playbook for stripping creditor rights that the entire industry now uses as standard operating procedure.

How do you move billions in assets out of a dying company and into a clean entity without the creditors being able to stop you? Who determines the value of what's being transferred when nobody is representing the other side? And how does Britney Spears end up at the literal center of a multibillion-dollar restructuring that kept this whole thing alive way longer than it should have survived?

And the biggest question of all (why we think this episode is mandatory listening right now): what happens when this playbook gets deployed AGAIN, today? We're already seeing the early signs: record levels of corporate debt coming due, earnings getting squeezed by higher rates, and redemption requests piling up. So what does creditor-on-creditor violence actually look like in practice? How do the alliances form and break? Why did the investors who got screwed the hardest in the Caesars saga end up being the biggest winners by the time the dust settled? And if you're sitting in any kind of debt instrument right now, how do you know whether you're the one holding the cards or the one about to get shut out in the cold?

Stay tuned for Part III, the conclusion of this 3-part series, where we'll be interviewing author and Financial Times reporter Sujeet Indap!

Shop our Self Paced Courses:

Investment Banking & Private Equity Fundamentals HERE
Fixed Income Sales & Trading HERE

Subscribe to our Substack: https://substack.com/@thewallstreetskinny