Larmer deserves his number retired long before JR or Chelios, and I'm not even sure he deserves his retired, necessarily. You can make an argument both ways, but generally speaking I think people are too quick and eager to retire numbers.
Loved Roenick as a Blackhawk and still do, but I really don't think he deserves his number retired here, and that's not really a criticism on him and not his fault. He had a great career here but just wasn't here long enough, in my opinion. Same goes for Chelios.
And Lincoln, I'd go easy on jumping all over someone for "being too young" to have watched certain players. You're the same person who said something along the lines of Keenan having nothing to work with on his rosters while coaching here if I do recall correctly...
IMO, if Magnuson is still alive, neither he nor Pilote get their number retired.
First off, Pilote and Maggie should not be mentioned in the same breath. PP, imo, is a borderline hall of famer, while no one had more heart than Keith but he just didn't have the skill of a Pilote.
As for the OP question. At the time, as a Hawk fan, I was proud that the Hawks gave him that chance to finish his career here. Excited in fact, but I think Bobby Orr himself, would be the first to laugh off the suggestion that his number be retired in Chicago after what went down. No, actually I think he'd be embarassed. Though his intentions to come to the Hawks where admirable, his knee was too far gone and he just coudn't go. It still saddens me.
And I have no doubt whatsoever, that he was better than Gretzky. It wasn't even close, in fact.