Mike Tyson
At one point, Mike Tyson was worth over $400 million, but in 2003, it was recorded that he was $23 million in debt. Tyson declared bankruptcy, went to jail, and entered a rehab program before he was able to return to financial stability. Right now, Tyson is relatively financially stable. He just started his own cannabis company, and he plans on expanding that company to a cannabis-themed resort when the pandemic ends.