<P> The first winner of the award was center Jean Béliveau of the Montreal Canadiens in 1965 . The first player and only defenseman to win it twice was Bobby Orr , who scored the Cup - clinching goals for the Boston Bruins in 1970 and 1972 . Goaltender Bernie Parent ( for the Philadelphia Flyers ) and centers Wayne Gretzky ( for the Edmonton Oilers ) , Mario Lemieux , and Sidney Crosby ( for the Pittsburgh Penguins ) have also won it twice each , with Parent , Lemieux , and Crosby each winning theirs back to back ( 1974 / 1975 , 1991 / 1992 , and 2016 / 2017 respectively ) . Goaltender Patrick Roy is the only player to win the trophy three times , and also the only player to win it as a member of two different teams ( with the Canadiens in 1986 and 1993 , and with the Colorado Avalanche in 2001 ) ; his wins also fall into three different decades . Ken Dryden , the 1971 Smythe winner , is the only NHL player to win this trophy before winning the Calder Trophy as rookie of the year ( in 1972 ) : Montreal called him up to play only six regular season games , which is not enough to qualify as a rookie season . Dave Keon 's eight playoff points in 1967 is the fewest ever by a non-goalie Conn Smythe winner , as he was a defensive forward and is the only Maple Leafs player to win the trophy donated by his club 's parent company . </P>
<P> The first winner of the award was center Jean Béliveau of the Montreal Canadiens in 1965 . The first player and only defenseman to win it twice was Bobby Orr , who scored the Cup - clinching goals for the Boston Bruins in 1970 and 1972 . Goaltender Bernie Parent ( for the Philadelphia Flyers ) and centers Wayne Gretzky ( for the Edmonton Oilers ) , Mario Lemieux , and Sidney Crosby ( for the Pittsburgh Penguins ) have also won it twice each , with Parent , Lemieux , and Crosby each winning theirs back to back ( 1974 / 1975 , 1991 / 1992 , and 2016 / 2017 respectively ) . Goaltender Patrick Roy is the only player to win the trophy three times , and also the only player to win it as a member of two different teams ( with the Canadiens in 1986 and 1993 , and with the Colorado Avalanche in 2001 ) ; his wins also fall into three different decades . Ken Dryden , the 1971 Smythe winner , is the only NHL player to win this trophy before winning the Calder Trophy as rookie of the year ( in 1972 ) : Montreal called him up to play only six regular season games , which is not enough to qualify as a rookie season . Dave Keon 's eight playoff points in 1967 is the fewest ever by a non-goalie Conn Smythe winner , as he was a defensive forward and is the only Maple Leafs player to win the trophy donated by his club 's parent company . </P>
who has won the most conn smythe trophies
who has won the most conn smythe trophies
Patrick Roy
Patrick Roy