Teeder Kennedy was the first player in NHL history to win five Stanley Cups and is the last Maple Leaf to win the Hart Trophy for most valuable player.
Kennedy 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.
The Stanley Cup final between Montreal and Toronto went five games, but is remarkable as each game required overtime to be decided. In the third game, with the series tied at one game a piece, Kennedy was twice the hero in the overtime. First, he prevented a goal by clearing a puck that was heading into the Toronto net, then, just fifty seconds later at the other end of the rink, he intercepted a clear-out pass from Montreal's Calum MacKay and scored to win the game. The fourth game was won by Toronto to lead the series 3–1.
It was in the next game of the series which Leaf defenceman Bill Barilko scored one of the most famous goals in NHL history with a goal in overtime to win the Stanley Cup. However, without Kennedy's face-off skills Barilko's heroics would never have occurred. Montreal had been leading late in the game 2–1 and it appeared that the teams would be playing a sixth game in Montreal. With just 39 seconds remaining in the game, Toronto was able to get a faceoff in the Montreal end. Toronto coach Joe Primeau had pulled the goaltender so they could have six skaters. Primeau had the option of changing his players, but decided to leave Kennedy out to take the faceoff against Canadiens Billy Reay. Kennedy's plan on the faceoff was to get the puck to Max Bentley, who was stationed at the point. Then Montreal coach Dick Irvin decided to switch and have his best forwards, the Punch Line, out for this critical faceoff. Kennedy would be facing Elmer Lach instead. Kennedy later recalled he was relieved at the switch as he had trouble with Reay on faceoffs, but when Lach came out he felt "I had a chance," Kennedy won the faceoff from Lach, got the puck to Bentley and from the ensuing scramble around the net Tod Sloan tied the game. The goal dispirited the Montreal team and led to Barilko's famed overtime goal which won another Stanley Cup for the Leafs.
1950–51 season would be Kennedy's last Stanley Cup. In the years following until Kennedy's retirement in 1957 the Leafs would either finish out of the playoffs or lose in the first round. However, Kennedy continued to play productive Hockey.
The Leafs never missed the playoffs in the years Kennedy played a full season.
Kennedy was inducted into the Hockey Hall of Fame in 1966