Isles: Present - I'd retire Charles Wang's jersey, symbolic of the man who drove the franchise into the ground (lower than even the prior owners ever could - and that's quite an accomplishment).
I would have only retired 22, 19, 5, 31 - keep things really exclusive and special but those dynasty players were eff'n warriors - they could all make a case for retiring numbers. Nystrom 23, Gillies 9 and I'd probably also add Tonelli's #27.
Leafs: Sittler 27, Salming 21, Clark 17, Sundin 13, Gilmour 93 (haven't seen the others play enough)
Gilmour didn't play long or win anything in Toronto but left quite a legacy. Same for Clark.
Today, with all the player movement and free agency, I dislike the idea of retiring a number. A franchise honouring a player but saying they represented something so special for the organization that nobody else can ever be associated with your contribution - that will become more and more rare nowadays.
And I would've hard times about reasoning for John MacLean. Probably not. He wasn't retired when he was all-time leader in offense and now we have Elias there with much more success.
Zach Parise and Adam Larsson (lol) are good bets for future. It'can go either way, really soon to judge.
As owner of the franchise I'd dang well hang these banners in my building:
Stan Smyl #12 Thomas Gradin #23 Harold Snepsts #27 Trevor Linden #16 Markus Naslund #19
Richard Brodeur #35
Doug Lidster #3
Tony Tanti #9
Mattias Ohlund #2
Henrik Sedin #33 (some day)
shared banner for captains Orland Kurtenbach & Kevin McCarthy #25
shared banner for Dennis Ververgaert & Pavel Bure #10
shared banner for Kirk McLean & Roberto Luongo (some day) #1
shared banner for Tiger Williams & Daniel Sedin (some day) #22
And honorary banners for:
I'd name a bathroom after Marc Crawford and a toilet after Dan Cloutier!
I'd unretire Briere's and just have Mario. >_> Crosby looks like he might not have enough longevity for the strict rules the Pens have, and Jagr is a dick who has burned every bridge, catwalk and/or viaduct there is.
That is a tough one. A young player who died before his potential could be reached. Is it worthy of retirement? That is a different debate, then you get into should the Rangers retire Boogaard, the Preds Belak, etc. etc. etc.
I wouldn't mind retiring MacLean's #15. That's the only one I'm agnostic over.
If Langenbrunner hadn't burned his bridges, I might have been in favor of a dual retirement of #15 in honor of both players once Jamie retired. (This is assuming Jamie went on to captain the team for years to come).
Certainly in the pantheon of the greatest & possibly best ever, Roy ranks right up there, and I further understand that in the dressing room, he was a tremendous guy, well liked, respected, a leader... still, I cant get over his outburst behind the bench, the public display of disrespect & the ignominious manner in which he left Montreal. Im just not that forgiving. I wouldnt even honor him...
As for Frank?. Is it necessary to continue twisting the knife? In perpetuity no less?.