 Kennedy had the reputation for excelling in the playoffs . He was the first player in NHL history to win five Stanley Cups and by just age 22 he had already won three Stanley Cups . Kennedy holds the Toronto Maple Leafs ' all @-@ time record for career points in Stanley Cup finals with 23 . He is the youngest player in the history of the NHL to have scored a Stanley Cup winning goal when he scored the winning goal of game 6 in 1947 at 21 @.@ 4 years of age . Until the Pittsburgh Penguins won the Stanley Cup in 2009 , with 22 @-@ year @-@ old Sidney Crosby as captain , Kennedy shared the honours with Wayne Gretzky as the youngest captains to have won the Cup . In 2001 The Hockey News assembled a panel of five hockey experts to choose the winners of a " would @-@ be " Conn Smythe Trophy , for best playoff performance , had the trophy been awarded prior to the 1964 – 65 season . Using microfilms of newspapers of the day and studying statistics and quotes from writers and coaches they chose winners from 1917 – 18 to 1963 – 64 . Of the players chosen more than once , only Kennedy was chosen as many as three times for his playoff performances in 1945 , 1947 and 1948 . He is fourth all @-@ time in playoff goals and sixth all @-@ time in points for the Maple Leafs 
