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 had purchased in 2001.
Maybe he should gamble with Jordan? No, that’s a bad idea, too!