5. Bernie Kosar
Kosar was an excellent quarterback for the Cleveland Browns. Furthermore, he won a Super Bowl with the Dallas Cowboys back in the day. The two-time Pro Bowl selection enjoyed a lengthy career and held many records until Tom Brady came along. Furthermore, because of the longevity of his time in the NFL, Kosar made a lot of money. In fact, his millions of dollars in income should have set him up for life.
Unfortunately, Kosar lost almost everything in 2009 when he declared bankruptcy. To sum up, this was like a box-ticking exercise in bad decisions. Firstly, there was a messy divorce that cost him about three million dollars. Then there were some terrible real estate investments and finally, his steakhouse went out of business. In the end, he lost about $15 million and had only about $44 left to his name.