I have a Loob jersey that my parents bought me during the 86 run. Definitely no regrets there, and my wife wears it to retro nights and also to any 80s theme parties we get invited to.
I bought a Val Bure jersey after one of his first games after the trade. He scored a hat trick against the oilers at home at a game I attended and I drunkenly bought his jersey. Not huge regrets.
A bunch of Iggy jerseys. I regret none of them, except maybe the Iggy Bruins jersey a little bit... I doubt I'll find a reason to wear that again any time soon. And I won't wear the Iggy Heritage one very often either, but I'll continue to pull it out for a game once a year or so.
I also have a bunch of blank jerseys. It's hard for me to get the name and number of players that are 20 years younger than me... just feels kind of weird. If I was getting one though I would lean toward one of the defensemen instead of a flashy forward. Russell, Wideman, Gio or Brodie, probably in that order.
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