http://fivethirtyeig...he-stanley-cup/
Lots (and lots, and even more lots) of good information and numbers and everything you would expect from Nate Silver, but this is what he believes is the issue:
First, bad luck is a major component. Even after accounting for the fact that Canadian teams have rarely been among the league’s best in recent years, you would still have expected Canada to pick up at least a couple of Stanley Cups at some point.
Second, the N.H.L.’s economic structure changed at an unfavorable time for Canada. During the first half of the 20-year drought, the league allowed teams to spend freely, but Canadian teams were hampered by the weak Canadian dollar. Since 2005, the Canadian dollar has recovered substantially, and Canadian teams are now turning large profits. But they are limited in their capacity to invest those profits in superior players because the league has instituted a hard salary cap.
Third, there is almost certainly a shortage of N.H.L. teams in Canada relative to the demand for hockey there and the revenues that Canada contributes to the league. Teams in nontraditional hockey markets like Raleigh, N.C., Tampa, Fla., and Anaheim, Calif., have won Stanley Cups since 1993, but without doing especially well financially. So have the Colorado Avalanche, who relocated from Quebec City in 1995-96. Had the distribution of N.H.L. teams more closely matched fan interest in the sport across the United States and Canada, Canada would have more teams in the league and – very probably – at least one Stanley Cup championship.
Finally, and related to the excess demand for hockey in Canada, Canadian teams routinely sell out their arenas at high ticket prices — whether or not they are any good. This may reduce their incentive to compete.