Shaquille O'Neal
Five years and three teams ago, Boston Celtics center/rapper/actor/ Comcast ( CMCSA) pitchman Shaquille O'Neal won an NBA title with Dwyane Wade and the Miami Heat. At the time, he was also trying to sell a house on Star Island in Miami Beach that he bought for $18.8 million in 2004. Sitting on 2.5 acres along 300 feet of Biscayne Bay waterfront, the 19,400-square-foot home had eight bedrooms, a two-bedroom guest house, a tennis court, an indoor racquetball court, a six-car garage and a pool splashed with the Superman logo.

Shaq tried to flip the house for what he felt was a reasonable $32 million to $35 million and in 2007 almost had a New York Yankees third baseman on the hook for $25 million. But he watched the estate linger on the market for five years amid a housing crisis that flushed Miami housing prices by nearly 40%, according to the Florida Association of Realtors.

Eventually, Shaq unloaded the house on Russian real estate magnate and Naomi Campbell paramour Vladislav Doronin in 2009 for a reported $16 million -- $2.8 million less than he paid and less than half his asking price. Shaq has since recovered, heading toward the playoffs as starting center (once he comes back from injury) of the NBA's East-leading Celtics, but only in the world of celebrity investments and bankrupcy can a $2.8 million to $16 million loss be considered getting off light.

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