#38: Jose Canseco
In 1988, Jose Canseco became the first player in baseball history to hit 40 home runs and steal 40 bases in one season. He was named MVP and earned tens of millions during his career. Off the field, though, his life was spinning out of control.
Divorces, legal fees, and years of lavish living drained his bank account. In 2008, he lost his house to foreclosure and admitted he was broke. Canseco turned to celebrity boxing matches, reality TV, and minor-league baseball to earn money, while writing tell-all books about steroids.
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