Former heavyweight boxing champ Mike Tyson is perhaps the least surprising entry in our list of rags-to-riches-to-rags athletes. An elementary-school dropout raised on the mean streets of Brownsville, Brooklyn, Tyson was savagely bullied until he began street fighting for money when he was 11 [source: Tyson].
After stints in a string of juvenile detention facilities, 13-year-old Tyson was taken under the wing of boxing trainer Cus D'Amato, who predicted the lisping, emotionally scarred brawler would become the youngest heavyweight champion in history. D'Amato was right.
At his peak, Tyson was earning $30 million for a single fight and is said to have earned more than $400 million during his roller coaster of a boxing career. A world champion at the tender age of 20, Tyson's bank account greatly outpaced his maturity. According to legal records from one of his two divorces, Tyson spent:
- $230,000 a month on cell phones and pagers from 1995 to 1997
- more than $400,000 on a single birthday party
- thousands more to care for the tigers roaming his Las Vegas mansion
Uneducated, emotionally stunted and desperate for a father figure, Tyson put his trust in characters like boxing promoter Don King, whom Tyson eventually sued for stealing tens of millions of his earnings [source: CNN]. The former champ filed for Chapter 11 bankruptcy in 2003 with debts of $23 million to the IRS, divorce lawyers, and an ex-wife.