#2: Mike Tyson
At only 20 years old, Mike Tyson became the youngest heavyweight champion in boxing history. His ferocious fights earned him an estimated $300 million or more. He spent like a king, buying mansions, fleets of luxury cars, and even pet white tigers. Nobody could slow him down.
The money vanished almost as fast as it came. Prison time, divorces, lawsuits, and wild spending caught up with him, and in 2003 he filed for bankruptcy owing about $23 million. Tyson slowly rebuilt his life, earning money from a one-man stage show, movie cameos, a podcast, and a cannabis business.
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