Hodge pointed me to an intriguing article by Daniel Tolensky, from everyone's favorite website, about who are potential buyers, wannabe's and sellers at this year's trade deadline. Tolensky uses suprising statistics to support his theory that Cinderella teams and even teams that are below top 7 in the NHL don't win the Cup (except the Devils in the 1995 lockout-shortened season, who finished in 9th) At least not since 1986, anyway. The stats below tell the story:

30% of the time the 1st Overall Team won the Cup
50% of the time a Top Three Team won the Cup
75% of the time a Top Five Team won the Cup
95% of the time a Top Seven Team won the Cup

To go one step further, let me add to those stats by adding 16 more years of history, (1970-present.)

41.6% of the time the 1st Overall Team won the Cup (thanks to the Oilers, Islanders, and Canadiens dynasties.)
63.8% of the time a Top Three Team won the Cup
86.1% of the time a Top Five Team won the Cup.
97.2% of the time a Top 7 Team won the Cup.

Of course there were less teams in the 70's.
You would think that these stats will change under the new Cap System. With the playing field becoming more even, the days of the dynasty are gone, and the chances of a Cinderella team winning are increasing.
Anyway, just stats for thought. Tolensky's article is worth a look.