Scottie Pippen $120,000,000
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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.
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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.
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