Estimated Career Earnings: $120,000,000
How He Lost It All: Scottie Pippen once spent over $4 million on a corporate jet that never took flight. Translation: No. 33 has spent a lot of money on some stupid shit. The Bulls legend lost millions through the cliched athlete formula of bad investments, lavish spending, and surrounding himself with attorneys who looted his fortune like it was Constantinople under siege. Jordan's sidekick isn't hurting as much after signing a deal with the Bulls to serve as a team "ambassador"—which, from what we can tell, means he sits courtside in a suit and smiles.