Simon played in the CFL from 1999-2013 with the Blue Bombers (1999-2000), Lions (2001-12) and Saskatchewan Roughriders (2013). He compiled a league record of 16,352 receiving yards over his 15-year career. His mark of 1,029 career receptions ranks second all-time, and his 103 career touchdown receptions are third all-time.
The wide receiver won three Grey Cup championships, claiming titles in 2006, 2011 and 2013. In his first title season in 2006, he was named the CFL's Most Outstanding Player after leading the league and setting career bests with 105 receptions, 1,856 receiving yards and 15 touchdowns.
Simon was selected as a CFL Western All-Star seven times and a CFL All-Star six times in his career. He was also awarded the CFLPA All-Star status four times. In his final season as a player, Simon won a championship, catching two touchdowns in Saskatchewan's title game in 2013.
After his Hall of Fame career, Simon transitioned to a career in sports management.
“When I retired, after my last game, I said that I wanted to be a general manager,” Simon said. “I worked towards that. I knew that I had to start from the bottom.”