Estimated Career Earnings: $25,000,000
How They Lost It All: Either Dermontti Dawson is the worst investor ever, or creditors are way too quick to loan this guy cash. When the seven-time Pro Bowler filed for bankruptcy in 2010 he listed just over $1M in resources and close to $70M in debts. How the hell does that happen? In what had to be a bizarre, passive-aggressive joke to his creditors, Dawson listed his "fake Rolex" and his daughter's dog "valued at $10" as assets.