This might be the most provocative choice on our list, but here goes. Doug Flutie was the quarterback at Boston College when he won the Heisman Trophy in 1984. After a short stint in the upstart United States Football League (USFL), Flutie moved on to the NFL, joining the Chicago Bears in 1986. Following a stint with the New England Patriots, Flutie went to the Canadian Football League in 1990 for eight seasons, playing for three different teams. Three times, he led his team to the Grey Cup championship. In 2006, Flutie was voted the CFL's greatest player in the modern era.