Warren Sapp
Warren Sapp amassed a fortune of $82 million during his time as an NFL player, and after retiring, he earned $45,000 a month as an analyst. However, he eventually filed for bankruptcy with just $826 to his name. He spent frivolously and eventually had to auction off all of his expensive luxury possessions as well as a Florida home to pay off his debts.
Dennis Rodman
Dennis Rodman is one of the best known players to have played in the NBA. During his basketball career, he managed to make about $25 million, but extensive spending got him in a bit of hot water. He owned $800,000 in child support as well as $50,000 is spousal support, leading him to declare bankruptcy.