Scottie Pippen $120,000,000
For someone who was always labeled as being notoriously tight-fisted with his money, the news of Pippen’s empty wallet came as a shock to most fans and former players. Between his NBA contracts, and endorsement deals, Scottie earned more than $120 million. Some say his losses are a result of “bad investments” and “poor planning,” but the details of how he lost this much money are still murky. The most well known of his bad “investments” was his purchase of a $4 million private jet in 2002. Pippen then spent another million to repair it … and then never used the plane. Don’t worry Scottie, MJ has a really nice jet, we’re pretty sure he’ll give you a ride.