I never agreed with O'Reilly. Middleton should be in the HHOF, which is an award in itself. O'Ree is a special case, I don't know why you even listed him. Bucyk, you have a point, but he's also a HOFer. The last two preceded most of the awards.
These are players that never won major individual awards, which was part of your criteria. I'm just pointing out awards have never had anything to do with getting a number retired as you're looking at a high percentage of the Bruins retired numbers that have never won a Hart, Selke, Conn Smythe, Norris.
Getting into the HOF is a career accomplishment, not an award which does help their case for getting a number retired. IMO, I think Krejci falls short of being HOF worthy but still should get his number retired for his importance to the team during one of it's more successful runs and his numbers relative to his peers.