For me, I grew up in Weymouth and Sheehan is from Weymouth and I saw him skating all the time down at the old rink before the fire.... If you consider the times he was a player; seeing him in a stinking Habs sweater is the ultimate "Dude What are you doing in that Sweater". He is a Boston boy for christ sake!!!
But, I am wondering why you picked Sheehan since he bounced around to more teams and leagues than any player I can think of.
Kaberle as a Bruin was just off to me.
Sergei Fedorov as a Duck/Jacket was weird.
Eric Lindros in a Leaf Jersey
Brian Leetch is a Leaf Jersey
Bobby Orr as a Hawk
Pavel Bure as a Ranger
Sundin as a Canuck
Saku Koivu as a Duck (Used to it now)
Being a younger generation fan, seeing Selanne as a Jet felt...dirty.
Rob Blake as an Av
Ray Bourque as an Av
Gretzky as a Blues
Players looking wrong in a Stars uniform:
Jaromir Jagr was weird at first, but I've been enjoying it this season
Stars players looking wrong in other uniforms:
Mike Modano (Red Wings) *facepalm*
Ed Belfour (Sharks and Panthers)
Derian Hatcher (Red Wings)
Brett Hull (Coyotes)
Joe Nieuwendyk (Panthers)
Marty Turco (Blackhawks and Bruins)
Brendan Morrow now with the Penguins