8. Scottie Pippen
6 NBA championships with Michael Jordan, forward for the Chicago Bulls
Estimated lifetime earnings: $120 Million
Pippen unsuccessfully sued his former law firm for losing $27 million of his money through poor investments. (He had earned about $110 million in salary alone over a 17-year career.) In February 2007—around the same time as Pippen’s failed NBA comeback attempt—the Missouri Court of Appeals upheld a ruling that the player owed U.S. Bank more than $5 million in principal, interest and attorneys’ fees from a dispute regarding a Grumman Gulfstream II corporate jet that he’d purchased in 2001. Speculation has been that Pippen cannot withstand the lawsuits financially and needs to play again to make his bills.
Maybe he should gamble with Jordan? No, that’s a bad idea, too!