NFL Hall of Famer, Warren Sapp, earned exactly $82,185,056 during his NFL career. In 2012, Sapp filed for bankruptcy. Apparently $82 million isn’t enough for a man with over 240 pairs of Air Jordans. In addition to his insane shoe collection, Sapp made sure that his mega mansion was fitted with a custom built INDOOR waterslide. Talk about living lavish! After retiring, Sapp had a brief stint as a studio analyst, but off the field troubles made him too much of a liability for the network.