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. After missing the entire 1955–56 season, he came out of retirement to play half of the 1956–57 season to help the Leafs who were short on players due to injuries and were struggling to make the playoffs. Kennedy returned November 27 to train himself back into shape after the Leafs had won only one game in their last 11. He scored 22 points in 30 games, but the Leafs finished out of the playoffs. He shared the captaincy with Jim Thomson. A highlight of the season was March 16, 1957, when the Maple Leafs scored 14 goals against the New York Rangers and Kennedy got four assists in what is still the Leafs' all-time record for goals in a single game. When it became clear the team was not going to make the playoffs, he sat out the last two games so the management could have a look at a young Frank Mahovlich. Kennedy said, "It was time for a new generation to lead the team." Mahovlich had practiced with Kennedy the previous day and, in expressing regret at never having played in a game with Kennedy said, "Teeder Kennedy's last practice was my first." During Detroit Red Wing Ted Lindsay's attempts to form a players' union in the 1950s, he was approaching selected leaders among the other five NHL teams. Although Kennedy was the lone holdout, which greatly disappointed Lindsay, he still respected Kennedy for not informing Conn Smythe about being approached. "I won't squeal", Kennedy told him. According to