19. Johnny Unitas
Unitas went from playing semi-professional football for six dollars a game to being the biggest star in the NFL. Furthermore, he enjoyed rare longevity as his career lasted for 18 seasons and he passed for over 40,000 passing yards. One of the greatest quarterbacks of all-time, the Super Bowl winner also made 10 Pro Bowl appearances. Furthermore, he went from making almost nothing to counting millions.
The Steelers’ legendary quarterback went down the classic route of pouring an insane amount of money into poorly-conceived business ideas. Also, he guaranteed all of his loans, which made him responsible for the bills if his companies went bust. Needless to say, most of them did and he lost over six million dollars. Just don’t buy real estate in Florida. It’s simply a terrible idea.