Estimated Career Earnings: $80,000,000
How They Lost It All: Terrell Owens taught us all valuable lessons about humility and burning bridges. The ancient, but totally serviceable receiver spent most of the last decade burying quarterbacks and burning teams to the ground; qualities GM's tend to overlook when you're scoring 15 TDs a season. But slower, older, and seemingly desperate for a contract, the league turned its collective back on the six-time pro bowler last fall, not good when you have bills to pay.

The fertile receiver has fathered four children by four different women and pays a prospectus-killing $50K a month in child support. He's made a series of bad investments including an entertainment complex that not only violated the NFL's policy on players investing in gambling, but was also illegal in the state of Alabama. Oops. And Owens got his ass-kicked (like many on this list) in real estate. He's turned property ownership into a cracked game of Monopoly, recently selling a New Jersey home that cost him nearly $4M for $1.7M.