[CorsiHockeyLeague]

Off the top of my head and with nothing but my faulty memory to support it...

1995-lockout: Western Conference absolutely dominated by Red Wings and Avalanche. If you didn't get massacred by one, you'd get killed by the other... and that's only if you made it past the Stars. The Flames / Oilers finals runs were underdog runs and both had some bad luck (Flames with the game 6 phantom goal; Oilers losing Roloson). Accordingly, you had to come out of the East, and the Brodeur Devils made that difficult. None of the EC Canadian teams were ever any better than mediocre during this period.

2007-2011: The Sens and Canucks runs were different from the prior two in that they were actually contenders. But it's still a coin flip in the finals, particularly against the two large, talented teams from the opposing conference, so no big surprise that they lost.

2011-Present: The current Blackhawks and Kings are basically the old-school version of the Red Wings and Avalanche. If the Blues or Ducks don't get you, one of them typically will (notwithstanding the conspicuous absence of the champs this year). In the East, it's the Pens and Bruins.

Honestly, upon reflection I think the real reason is that in any given year, you had 6 Canadian teams, and at least 3 were probably going to be outright bad teams. That leaves you with a 10% chance every year at the cup. Realistically, though, for the first 10 years, the deck was stacked in the Western Conference with powerhouse Detroit, Avalanche and occasionally Dallas teams, so that cuts your chances further. At that point it's a roll of the dice, and it's not surprisng when your sub-10%-shot doesn't pan out.