Simon grew up playing hockey for Shaker Heights High School as well as Team Ohio Midget AAA and the Cleveland Junior Barons.[3]
He was drafted 110th overall by the Chicago Blackhawks in the 1997 NHL Entry Draft and has played 81 games in the NHL with the Atlanta Thrashers and Columbus Blue Jackets, scoring three goals and one assist. In the 2007–08 AHL season, he played for the Springfield Falcons. For the 2008–09 season, Simon played with the Iserlohn Roosters in Germany's Deutsche Eishockey Liga. In July 2010, he signed up for his first coaching role, as Player/Coach for the Sheffield Steelers in the British Elite Ice Hockey League for the 2010–11 season. After winning the regular season championship with the Steelers, Simon decided not to return to the Steelers for another season.