Theodore played 16 seasons in the NHL in a career highlighted by his performance in 2001-02, when he became the third goalie in League history to win the Vezina Trophy as top goalie and the Hart Trophy as most valuable player in the same season.
The Montreal Canadiens selected Theodore in the second round (No. 44) of the 1994 NHL Draft. He made his NHL debut in a relief appearance against the Hartford Whalers on Feb. 21, 1996, split the next three seasons between the Canadiens and Fredericton, their American Hockey League affiliate, and became their starter in 2000-01, finishing 20-29 with five ties, a 2.57 goals-against average and a .909 save percentage. He also became the sixth goalie to score a goal when he shot the puck into an empty net in a 3-0 win against the New York Islanders on Jan. 2, 2001.