10. Raghib Ismail
If you know about Ismail’s early professional career, then it will be a surprise to see him on this list. He rejected the NFL draft simply because the Canadian Football League offered him almost $20 million to come and play north of the border. Ismail duly obliged and spent two years with the Toronto Argonauts on the biggest contract in football before moving to the NFL, where he enjoyed 10 seasons.
He left the sport with an obscene amount of wealth but lost it all because of a series of brutal investments. Firstly, there was a religious movie, then there was a music label. He even invested in a custom calligraphy shop chain. We’re not sure why any of these seemed like good ideas but it cost him about five million dollars. When you add in all the taxes and outside expenses, it was even more.