If Canadian teams were constantly struggling and finishing at the bottom of the league, there might be value in trying to figure out why Canadian teams are having trouble competing, but they're not.
Since 2004, 22 different teams have played in the Stanley Cup Final. 5 different Canadian teams have played in the Final in that time. The Flames, Oilers, and Canucks were all one win away from the Cup. The Flames and Canucks both had 3-2 series leads in the Finals.
Since the lockout season, the Canucks have won the President's Trophy twice, and the Senators, Canadiens, Jets, and Flames have all finished second overall in the regular season at least once each.
Canadian teams haven't been struggling, they just haven't won the Cup, but a lot of teams haven't won the Cup. This will be the 27th time the Cup is presented since the Habs last won. In that time, only 14 different franchises have won it, which means 17 franchises haven't.
Also, keep in mind that when the Habs won in 1993, it was the 8th time in 10 years the Cup had been won by a Canadian team. These sorts of things go in cycles. Remember that a lot of recent winners ended long droughts of their own when they won: St Louis had been around for more than 50 years when they finally won; Washington and LA were about 45 years; Chicago's Cup drought was nearly 50 years and Boston's was almost 40 years.
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