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The Thesis
Apollo Global Management acquired Caesars Entertainment and navigated one of the most complex restructurings in history, ultimately preserving and growing value through operational improvements and real estate monetization.
The Story
Apollo Global Management, co-founded by Leon Black, acquired Caesars Entertainment (then Harrah's) in a $30 billion leveraged buyout in 2008 — right before the financial crisis. Like Blackstone's Hilton deal, the timing appeared terrible. Caesars was loaded with debt, and the casino industry was hit hard by the recession. The company eventually filed for bankruptcy in 2015.
However, Apollo's team executed one of the most sophisticated restructurings in corporate history, separating the real estate assets from the operating business, negotiating with creditors, and preserving significant equity value through the process. The gaming industry recovered, and Apollo ultimately generated strong returns on its invested capital. The deal demonstrated Apollo's expertise in complex situations — the willingness to navigate through bankruptcy and restructuring rather than abandoning ship.
Key Insight
In private equity, the ability to navigate complexity and restructuring is as valuable as picking the right assets — deals aren't over when things go wrong, they're just entering a new phase.
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See how Glen Bradford applies these principles to his own investing. Long Fannie Mae & Freddie Mac junior preferred — conviction meets patience.