1965 - Jean Beliveau
It's fitting that a Montreal Canadien was the first winner of the Conn Smythe Trophy. It's even more fitting that the winner was Jean Beliveau. "Le Gros Bill" was one of the greatest NHL players ever and deserved the Conn Smythe to add to his trophy collection. It's interesting to wonder how many of these trophies Beliveau could have had if the award had been around during his first five Stanley Cups. Beliveau had 16 points in 13 games to lead the Habs to his sixth of ten titles.
1969 - Serge Savard
Savard was the first defenseman to win the award and one of just 10 men to do it. Savard eventually won eight Stanley Cups as a player and two as a General Manager, factoring into the last ten Cups in Montreal Canadiens history. Savard was integral in each, but his best performance came in 1969 when he shut down the other team's biggest stars and recorded 10 points in 14 games.