Fantastic article - thanks to the OP.
One other consideration that I would like to throw out there is cyclicality.
In the late 80s / early 90s, Edmonton, Calgary and Montreal were all strong teams and were due for a period of rebuilding, which, due to the dollar, came at a very unfortunate time. As a result of financial constraints, those recovery cycles were severely challenged, deepened, and lengthened. As mentioned, then came the cap - also very unfortunate timing.
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Even though there has been a cap for the past 8 seasons, there have still been 4 Canadian teams in the finals in the last 9 years and, as the author said, 3 of them went to game 7. So a bit of bad luck there and it probably isn't as bleak as the headline of 20 years would suggest.
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