 Although young , Kennedy was successful with Toronto from the start . In his first season , the 18 @-@ year @-@ old finished second on the team in scoring and then in his sophomore year was considered the star of Toronto 's upset of the record @-@ breaking Montreal Canadiens of 1944 – 45 . He would establish himself as the leader of the team and became captain in 1948 . Although not the best skater in the league , Kennedy was a fierce fore @-@ checker and skilled playmaker . Kennedy would be a perfect fit into coach Hap Day 's emphasis on defense and positional play . He gained a reputation for scoring the important goal and excelling in the playoffs . Kennedy holds the Toronto Maple Leafs ' all @-@ time record for career points in Stanley Cup finals and is the youngest player in the history of the NHL to have scored a Stanley Cup winning goal . A Sports Illustrated poll of hockey experts in 1998 rated Kennedy as having the best face @-@ off skills in the history of the NHL . 
