Raghib Ismail
“The Rocket” caught the public eye when he played for Norte Dame, he then went on to record two 1,000-yard receiving seasons while in the NFL and was a CFL All-Star in 1991, and was also the Most Valuable Player of the 79th Grey Cup. However he invested a ton of money on numerous unsuccessful business ventures, including attempting to open a restaurant franchise similar to the Hard Rock Cafe.
Lawrence Taylor
No doubt about it, Taylor was one of the greatest defensive players to ever take the field, especially during his time with the New York Giants. In his career, Taylor earned around $50 million while making Pro Bowl after Pro Bowl. Just five years after retirement, he filed for bankruptcy and some time later, was found guilty for tax evasion.