3. Latrell Sprewell

Ride: “Milwaukee's Best” yacht, 2001
Complex Says: Although a major part of a late-'90s New York Knicks team that made it to the NBA finals, Latrell Sprewell will always be best known for losing control and choking his coach, P.J. Carlesimo, while playing for the Golden State Warriors. Fast forward to post-basketball, and Sprewell again lost control, but this time of his finances, due in part to an Italian-made, 70-foot-long private yacht that he purchased for $1.5 million. Sprewell named the yacht “Milwaukee's Best,” after his hometown. But in 2007, a bank foreclosed when Sprewell failed to pay the boat's mortgage. Sprewell, who was also dealing with a foreclosure of his Milwaukee County home at the time, managed to sell the yacht at auction for $856,000. He still owed the bank nearly $500,000. The irony of the four-time all-star's financial woes is that he had turned down a three-year, $21 million contract extension from the Minnesota Timberwolves at the start of the 2004-2005 season, claiming, “I've got my family to feed,” as though the amount wasn't enough to keep food on the table.