Four-time NBA All Star; last played for the Timberwolves
Estimated lifetime earnings: $50 million
This 13-year NBA veteran turned down the Timberwolves’ $21 million offer to extend his contract for three years because the sum was too low. A mere three years later, federal agents repossessed Sprewell’s yacht, on which he still owed $1.3 million. That was just the beginning. In early 2008, Sprewell defaulted on a $1.5 million mortgage, lost his home to foreclosure, stopped paying his motorsports’ company’s bills, and then defaulted on another home loan, this one worth $10 million.