Should have been here sooner? The Leafs have had 34 and 16 for 8 years and won one round one time. The Oilers have at least won a few rounds on their way to this season.
And with all due respect to Sid, Edmonton is still Edmonton so it's still a valid "excuse" to a degree. Had McDavid and Draisaitl not been drafted by the Oilers the chances of the Oilers ever acquiring either or both of them would be less than 0%. The difference between a Canadian team (especially a small, shithole market like Edmonton, Calgary, Ottawa, or Winnipeg) and a US team is precisely that: the ability to reach out and grab a superstar free agent or be a team that isn't on every players NTC list. The Rangers and Panthers never have to ask themselves "I wonder if he would waive his no trade for us?" whereas for franchises in Canada it's literally the first question they have to ask.
The Oilers are in the finals today because of McDavid, the rest of the team stepping up, and a bit of puck luck. Without that first element the other two would be irrelevant and the Oilers would have been golfing weeks ago. So this isn't about "building a great franchise, yada, yada, yada." It's about being lucky enough to have a generational player in his prime, playing at a high level at the right time of the season. In this way the Oilers run is just as much a function of luck as the Habs' 2021 run was. Any time a Canadian team goes to the final it is, by definition, an outlier. A fluke. It isn't something that is ever "supposed" to happen. The entire NHL system is designed to ensure that the chances of it happening are always remote. Not impossible, but pretty close.
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