Best Chance For the Toronto Maple Leafs To Win The Stanley Cup, Post-1967?

It's been 45 years since the Toronto Maple Leafs have last hoisted the Stanley Cup. T their credit, their victory that year was a surprise, most people thinking the Chicago Balck hawks were going to win, but since then they've yet to beat the odds and win the Cup. They have never even been to the Stanley Cup Finals since then. However, they have made it to the semi-finals a few times...

1993: The Leafs defeated the Detroit Red Wings and the St. Louis Blues to reach the semi-finals to face Wayne Gretzky the Los Angeles Kings. They manged to get a 3-2 series lead when a controversial Game 6 took place. Gretzky high-sticked Doug Gilmour in the chin, with the game tied 4-4. He should have been given a penalty but wasn't, and he went on to score the game winning goal, tied the series 3-3, and then went on to score a hat trick in Game 7, beating the Leafs.

The Kings would then go on to face the Leafs great rivals, the Montreal Canadiens, who would win the Stanley Cup in 5 games.

1994: This time, the Leafs beat the Chicago Balck Hawks and the San Jose Sharks on their way to their back-to-back semi-final appearances. In it, they faced the Vancouver Canucks, and while the Leafs were able to win the first game, they lost all the rest, losing the series 4-1. They were however able to make the Canucks work for it, by pushing them into double overtime in Game 5.

The Canucks would go on to play a full 7 games against the New York Rangers, who were able to end a Stanley Cup drought of their own, winning the series 4-3.

1999: The Leafs beat two Penn State teams, the Philidelphia Flyers and the Pittsburgh Penguins to make it to the semi-finals for he first time in five years. Facing off against the Buffalo Sabres, they would lose the series 4-1. The Sabres would go on to face the Dallas Stars, who would win the Stanley Cup on a controversial goal from Brett Hull in triple-overtime.

2002: This is the last time the Leafs have made it to the semi-finals. Toronto would beat both the New York Islanders and the Ottawa Senators on their way to facing the Carolina Hurricanes. Games 2,3 and 6 of the series went into overtime, and all of the games except Game 4 were won on a won goal lead.The Hurricanes went on to face the Red Wings, who won that year in a 4-1 series.


Since then, the Leafs haven't even made the playoffs since 2004. Who knows if they'll be able to turn that around. My question is, of the four times listed above, which one is the best chance for the Leafs to advance to the Finals, and win the Cup? Don't just think about how they can win in the semi-finals, but also who they would beat their would be opponents in the Finals. Ignore Butterflies and assume that they would have faced the Canadiens in '93, the Rangers in '94, the Stars in '99 and the Red Wings in '02.

What do you think might have been?
 
Ah, something close to my heart.

Personally, I think 1993. 1999 followed by 1994. I don't think the 2002 Leafs could have beaten 2002 Detroit (as much as I hate to admit it, that team was good).

1993 - As you say, the LA series could have gone either way. Obviously, we don't know if Toronto could have won that game 6, but let's say Gilmour scores the winner and Toronto goes to the final.

I remember growing up, I would watch the VHS of the LA/Montreal series. Montreal dominated LA. Toronto, I think would have been a different story.

Goaltending: Potvin vs. Roy - had to say, both were incredible back then, but my money would be on Roy (despite my intense dislike of him). Although, I think the difference would be negligible.

Defense: Both teams are pretty solid.

Offense: I like Damphousse, but that Toronto team was stacked. Gilmour, Andreychuck, Clark...

Coaching: Demers was good, but Burns had the heart.

Overall, I think Toronto could have beaten the Canadians.

2002 - We had a good team, but I just don't think we could have beaten the Sabres

1994 - Again, could beaten the Canucks, but I think the Rangers would have been tough. They seemed a lot like the Leafs, would have been a great series.
 
Truthfully, 1993 is by far the best chance, and it could have been different had Ballard had a little more foresight in 1988, when Peter Pocklington came to him about trading a certain Oilers star because Pocklington needed money and the player in question wanted to move....
 
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