Some of this is meant to be tongue-in-cheek, while others are brutally honest. If you have any suggestions for improvement, fire away!

Anaheim: (Used to be) Mickey Mouse ownership
Atlanta: William Tecumseh Sherman
Boston: "MAY DAY! MAY DAY! MAY DAY! MAY DAY! MAY DAY! MAAAAAAY DAAAAAAY!"
Buffalo: McKinley Assassination, Red Jacket's Firewater
Calgary: Employing firefighters since 1989
Carolina: Reverted back to Hartford Whalers mentality since Cup win.
Chicago: Always blown over in the Windy City. Also, there's firewater in the ice.
Colorado: Colorado Kool-Aid (aka Coors) Stupor since last Cup win.
Columbus: Dwarfed and overshadowed by Ohio State University.
Dallas: Skate in the crease is still haunting them (regardless of your feelings of the situation). (Sorry, No Longer A Libertine, but something had to get thrown in there.)
Detroit: The wheels have come off since Scotty Bowman retired
Edmonton: Not the same since Gretzky and Kurri left
Florida: Rats-B-Gone
Los Angeles: Forget the Triple Crown Line -- they've never won the Crown!
Minnesota: The Wild are Tame
Montreal: Leaving the Forum has haunted them
Nashville: Music matters more than hockey and Blackberries
New Jersey: Dagobah
NY Islanders: Al Arbour needs to come out of retirement
NY Rangers: 1940, 1994, 2048 (Guess when their next cup win will be???)
Ottawa: 1927!!!
Philadelphia: Bush league doesn't work in today's hockey like it did with the Broad Street Bullies
Phoenix: SWIFT!!! (Truckers would understand this)
Pittsburgh: Lack of supporting cast for the Sid the Kid show
San Jose: Since when do Fish hold sticks?
Saint Louis: Singing their namesake
Tampa Bay: Bolted down by the Fonz since Cup win
Toronto: Last team to win the Cup in Original Six era. Needs other 24 teams to fold to win again.
Vancouver: Where's Johnny Canuck when they need him?
Washington: Beltway Gridlock (DUH!)

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No one needs to really know who I am or where I go to church or what I believe in now. None of this is relevant because I am no longer affiliated with this messaging board.