Mike Tyson
When an expert fighter, Mike Tyson is known for the vast majority of insane things. Indeed, he nibbled a piece of somebody’s ear off in a battle and was captured many times. And the fact that he was worth around $400 million at a certain point, his life was not all daylight and rainbows. His spending was silly, purchasing outlandish creatures and many houses he disregarded yet purportedly all while being underwater somewhere in the range of $30-60 million.