 Smythe was able to talk Kennedy into playing the 1954 – 55 season . At the conclusion of the season , he would win the Hart Memorial Trophy , for most valuable player , and is the last Toronto Maple Leaf to have won the trophy . To this point Kennedy had had an impressive career . He had played on five Stanley Cup teams , something no other NHL player had achieved at the time . Toronto had only missed the playoffs twice during his eleven years , one of which Kennedy was injured . By age 22 he had won three Stanley Cups and was the youngest player to have scored 100 goals . Yet , Kennedy had never won an award , nor been elected to a first All @-@ Star team . Although he did finish third in the league in assists , awarding Kennedy the Hart was considered as much as an acknowledgement of his career as his performance in the season . Kennedy along with first ever Hart recipient Frank Nighbor , are the only forwards to have won the award without finishing in the top ten in league scoring . After the Leafs were swept in four straight games in the playoffs by the Detroit Red Wings , Kennedy announced his retirement . For the second time , Kennedy was awarded with the J. P. Bickell Memorial Trophy as most valuable Toronto Maple Leaf . 
