I think the issue for me is that these guys are still too current. The old conference names and the award names are mostly guys from old time hockey and help ground the game in it’s past. At some point fans will see Gretzky, Lemieux, and Messier that Nailed it vintage shirt, but it’s too soon in my opinion. Edit: With the exception of Gordie Howe, he would fit, but screw that Red Wing s.o.b.! (not really).
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I think it depends. Retiring old trophies and using new ones would be the Nailed it vintage shirt, but even then the trophies would have to be named after some very big stars. It would also require much more time to pass. These players we’re talking about are great, they’re in the hall of fame, but they don’t really need anything more. Maybe in 20-30 years it’ll be a different story.