Simon was drafted 25th overall by the Philadelphia Flyers in the 1990 NHL Draft, and went on to play a 782 game career with eight different teams: the Nordiques, Avalanche, Capitals, Blackhawks, Rangers, Flames, Rangers, and Wild. Simon was one of the most feared enforcers through the 1990s, amassing 1824 penalty minutes in his career. He also won the cup with the Avalanche in 1996.