Michael Jackson
The King of Pop was in quite a bit of debt-- about $400 million of it-- before he died suddenly in 2009. Neverland Ranch was taken by the bank before he passed, and his CFO was able to sell the mansion to cover the rest of his payment in his wake. Oddly enough, Jackson would later become the top-earning dead celebrity in 2012, making Sony a massive paycheck of profit in his absence.
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