 I saw some photo of a Packers fan wearing a Aaron Rodgers jersey and it made me think about how nice (but risky) of a gesture that is. That made me think further: what jersey(s) should fans of each NHL team consider?
Here is my criteria:
1. A solid crossroads of obscurity and talent
It's not very exciting to wear a Crosby jersey if you're a Penguins fan or an Ovechkin jersey if you're a Caps fan ... so you want to get a sweater that's a little more unique. That being said, you don't want to wear the number of a guy who can barely play 10 minutes a night. Finding a good compromise between the two is ideal.
2. Longevity
This is a big one in a sports atmosphere where players change colors so often. Trying to find a guy who either has a longterm deal or is unlikely to leave is a key component to finding the right jersey.
3. General Goodwill
More in line with your fellow fans, general goodwill is measured by how your peers would react to that jersey.
Optional Categories:
4. Sentimentality
To contrast #2, some players build up enough goodwill that you can permit people to wear a rosterly outdated jersey. This does not apply to guys who leave on bad terms (so just go ahead and burn that Heatley Senators jersey or that Pronger Oilers jersey).
5. Hilarity
Special bonus points go for players who were horrible. You get instant respect from me if you rock a Tommy Salo Team Sweden jersey, a Roman Cechmanek LA Kings jersey or something of that ilk. 
***
Anaheim
Active Teemu Selanne Jonas Hiller
Departed Guy Hebert Steve Rucchin
Atlanta
Active Bryan Little Colby Armstrong
Boston
Active Milan Lucic (even though it's pretty obvious) Zdeno Chara (breaks the rules because he's super tall)
Departed Bobby Orr (obvious ... but it's Bobby effin Orr) P. J. Axelsson (judging from Cornelius's man crush)
Buffalo
Active Thomas Vanek Derek Roy
Departed Chris Drury Daniel Briere
Calgary
Active Jarmoe (he's just too bad ass) Robyn Regehr
Departed Theo Fleury Al MacInnis
Carolina
Active Chad LaRose Rod Brind'amour
Departed Ron Francis - Hartford Whalers edition Chicago
Active Brent Seabrook Kris Versteeg
Departed Jeremy Roenick Stan Mikita
Colorado
Active Craig Anderson Kyle Quincey
Departed Pretty obvious, right?
Columbus
Active Antoine Vermetteg Jan Hejda
Dallas
Active James Neal Brenden Morrow (he's just too bad ass)
Departed Neal Broten - North Stars Mike Modano - in his prime (just kidding) Sergei Zubov
Detroit
Active Darren Helm Johan Franzen
Departed There's about a million
Edmonton
Active Sam Gagner Ales Hemsky
Departed Again, lots. See: the 1980's
Florida
Active David Booth Tomas Vokoun
Departed Bieser
 Los Angeles
Active Dustin Brown Drew Doughty
Departed Kelly Hrudey Luc Robitaille
Minnesota
Active Miikko Koivu Brent Burns
Montreal
Active Andrei Markov Michael Cammalleri
Departed C'mon
New Jersey
Active Zach Parise
Departed Scott Stevens Scott Niedermayer
New York Islanders
Active John Tavares (before fans come back out of the woodwork?) Kyle Okposo
Departed See: Edmonton
New York Rangers
Active Ryan Callahan Michael Del Zotto
Ottawa
Active Anton Volchenkov Mike Fisher
Departed Alexandre Daigle :)
Philadelphia
Active Mike Richards (because he's so bad ass) Braydon Coburn
Departed Someone who hurt a lot of people
Pittsburgh
Active Max Talbot Tyler Kennedy
Departed Beyond the obvious ... (to me anyway) Straka, Kovalev, Wregget, Kasparitis, etc.
San Jose
Active M.E. Vlasic Joe Pavelski IF he re-signs
St. Louis
Active T.J. Oshie Erik Johnson
Departed Adam Oates Brett Hull Al MacInnis
Tampa Bay
Active Steve Stamkos Victor Hedman
Toronto
Active Luke Schenn Phil Kessel
Departed Mats Sundin Wendel Clark 
Vancouver
Active Ryan Kesler Alex Burrows
Departed Trevor Linden Pavel Bure
Washington
Active Nicklas Backstrom Howeverhespellshisfirstnamenow Varlamov
Departed Olaf Kolzig Petr Bondra
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