I wanted to dig deeper into Kennedy's reputation as a playoff legend. Here's how he performed in each of the playoff series where his team won the Stanley Cup (this is just from box scores, so I can't speak to his defensive play, leadership, etc):
1945
In the first round, Kennedy helps lead the Leafs to a huge upset against Montreal (the Habs finished 28 points ahead in the standings - absolutely massive during a 50 game season). In the first game, Kennedy scored the sole goal, unassisted, with less than a minute to go in the third period. He scores the opening goal in the next game (the Leafs win 3-2). Kennedy goes scoreless in a 4-1 loss in game three. He records one assist (not on the game-winner) in the 4-3 OT victory. He scores one goal in a blowout loss in game five. The only disappointment? He's scoreless in the decisive game six. Still, he led the Leafs in goals, and tied for the team lead in points.
The Leafs are also underdogs against Detroit. They must have shocked the hockey world with three straight shutouts (Kennedy scores the first of the Leafs' two goals in the second game). Detroit storms back with three straight wins. Hard to fault him in game 4, as he scores two goals in the first period only a few minutes apart. In game 7, the Leafs win the Stanley Cup, but Kennedy's scoreless. Overall, Kennedy decisively leads the team in goal-scoring this series (he's the only Leaf with more than one goal!) He also leads the SCF in overall scoring.
1947
This time, Kennedy's Leafs are heavy favourites against Detroit. It was a weird series. The Leafs needed overtime to win game 1 (Kennedy gets two assists, including the game-winner). Detroit demolishes Toronto 9-1 in the next game (Kennedy scoreless). Then the Leafs pummel the Wings by a combined score of 14-3 to finish the round (Kennedy has a goal and an assist). Kennedy is tied for second on the team in scoring behind, surprisingly, defensive specialist Nick Metz.
In the finals, the Leafs face Montreal (the slight favourites on paper). The team trade blowouts in the first two games - Kennedy got a goal and an assist in the first two minutes of game 2, which the Leafs ended up winning 4-0. In game 3, Kennedy scores an insurance goal late in the third period to make it 4-2. Kennedy's scoreless in the next two games, close ones where the teams trade victories. The Leafs win the Cup in game 6. Kennedy assists on the tying goal in the second period, then scores the Cup-winning goal with just over five minutes to go in the third. Kennedy ties for the team lead in goals and points this series.
1948
The Leafs are significant favourites against the Bruins on paper. The Leafs win the first game 5-4 in overtime; Kennedy assists on the tying goal with less than five minutes to go. In the next game, Kennedy single-handledy demolishes the Bruins, scoring four goals. I want to be clear that none of these are blowout goals - one opened the scoring, two of them re-established a lead after Boston tied the game, and the last of them (scored barely halfway through the contest) gave the Leafs a two-goal lead. Kennedy has another excellent performance in game 3, with a goal and two assists (only the last helper, which made it 4-1 with exactly 13 minutes to go, can be considered gratuitous). Kennedy's held scoreless in the Leafs' game 4 loss. In the decisive game 5, Kennedy assists on the tying goal in the first period, and scores the series-winning goal in the third period. This may have been Kennedy's best series - 10 points in five games (in a low-scoring era), with nearly every point being important to the outcome of the game.
Next, Toronto played Detroit in the finals. They finished five points behind the Leafs in the standings, but were swept. Kennedy has an assist in game 1 (on a goal that made it 5-1 late in the second). He was held scoreless in game 2, a comfortable Toronto win. He assists on the insurance marker late in the 3rd period in game 3. Kennedy scores two goals in the decisive fourth game (the opening marker, and one that turned this into a route). A quieter series for Kennedy.
1949
The Leafs regressed in the standings and faced off against a much stronger Boston club. Kennedy is scoreless in the Leafs' first two victories. They lose game 3 in overtime, but it's hard to blame Kennedy - he scored the opening goal, assisted on a goal that cut Boston's lead to one late in the second, and assisted on the tying goal with eight minutes to go in the third. In game 4, Kennedy records two assists - on the go-ahead goal midway through the second, and an insurance marker late in the third. He's scoreless in the decisive fifth game. Kennedy ties for the team lead in scoring.
In the finals, the Leafs play the Red Wings for the second year in a row. Detroit is a much superior team on paper (18 points higher in the standings), but Toronto sweeps. Kennedy is scoreless in game 1, which went to overtime. He assists on two important insurance goals in game 2. He scores what proves to be the game-winner partway through the second period in game 3. He's scoreless in game 4. A less impressive performance for Kennedy.
1951
This time the Leafs are enormous favourites (33 point advantage in the standings). The Leafs are shut out in game 1. Game 2 is called a tie (anybody know why?) - Kennedy is scoreless. He's shut down entirely in games 3 and 4 (both wins) - so that's now four straight pointless games. He scores one goal in game 5 (which made it 4-0 halfway throug the 3rd - probably not the most important goal). In the blowout game 6, Kennedy scores the opening goal, then assists to make it 5-0 halfway through the third. This is by far the least impressive series for Kennedy - arguably just one "significant" goal in six games against a heavy underdog.
The Leafs play a much weaker Habs team in the finals. This series is significant because all five games went to overtime. The Leafs win the first game; Kennedy assisted on the opening goal just fifteen seconds into the game. The Leafs lose game 2, but Kennedy assisted on the Leafs' first goal late in the second to cut the lead to one, and then scores the tying goal halfway through the third. In game 3, Kennedy scores the overtime goal. Kennedy assists on the opening goal in game 4 (also less than a minute into the match). In the decisive game 5 (this was the one where Bill Barilko scored the overtime winner - as popularized by The Tragically Hip), Kennedy assists on the tying goal midway through the second. He finished tied for second on the team in scoring.
Overall assessment
During these five years, Kennedy played in all 53 of the Leafs' games. He scored 25 goals and 24 assists for 49 points. If we look at the span of seven seasons from 1945 to 1951 (so this includes 1946, when the Leafs missed the playoffs, and 1950, a first round loss which I didn't cover above), Kennedy leads all players in playoff assists and points, and is runner-up to Maurice Richard in goals. He's third in points per game, behind only the Rocket and Max Bentley (minimum 40 games).
Kennedy's playoff resume is like the anti-Dionne. One thing that jumps out is he frequently scores or assists the opening goal. That might not have meant much in the high-scoring eighties, but scoring the opening goal in his low-scoring era was more important (it's late but if I've added this correctly, he scored or assisted on the opening goal 10 times in 53 games). He also came up big - he scored or assisted on 8 goals in overtime, or winning or tying goals in the third (that excludes insurance goals altogether). Kennedy was consistent (he just had that one bad stretch in the first round in 1951). Furthermore, as I've shown, he rarely recorded points in blowouts - there are a few, but I'd be willing to bet it's a lower percentage than most other playoff performers we'd rank around his level ie Sakic, Messier, Lafleur.
(Despite what I said on the first page - that his 1955 Hart trophy was probably just a retirement gift - Kennedy will get a serious look at my top three for this round).
"First goals" scored or assisted (first goal of the game - not just for the Leafs)
- 1945 (round 1, game 1) - scores first & only goal of game
- 1945 (round 1, game 2) - scores first goal
- 1945 (round 2, game 2) - scores first goal
- 1947 (round 2, game 2) - scores and assists on first two goals in first two minutes of game
- 1948 (round 1, game 2) - scores opening goal in his four-goal game
- 1948 (round 2, game 4) - scores first goal
- 1949 (round 1, game 3) - scores first goal
- 1951 (round 1, game 6) - scores first goal
- 1951 (round 2, game 1) - assists on first goal less than a minute into the game
- 1951 (round 2, game 4) - assists on first goal less than a minute into the game
Winning or tying goals in 3rd period or OT (insurance goals excluded entirely, even if important)
- 1945 (round 1, game 1) - scores game's only (and therefore) winning goal, a minute left in 3rd
- 1947 (round 1, game 1) - assists on OT winner
- 1947 (round 2, game 6) - scores Cup winning goal with five minutes to go in third
- 1948 (round 1, game 1) - assists on tying goal with five minutes to go in third
- 1948 (round 1, game 5) - scores series-winning goal in third
- 1949 (round 1, game 3) - assists on tying goals with eight minutes left in third (Leafs lose in OT)
- 1951 (round 1, game 2) - scores tying goal halfway through third (Leafs lose in OT)
- 1951 (round 1, game 3) - scores OT winner