Sheryl Swoopes
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She was, unquestionably, the WNBA’s biggest superstar. She won four consecutive championships with the Houston Comets, she won an Olympic gold medal, and she even had a shoe line named after her. But throughout her career, Swoopes made a series of poor financial investments, spending freely along the way. By the time her career ended, she had to part with many beloved mementoes, just because she couldn’t afford the storage unit rent.