Papazoola, I'm afraid I just don't see it the way you do at all.
If Glenn doesn't restructure his contract, who on earth might Kelly think he is going to trade him to at his current starter's salary? And if he does somehow manage to trade him at his starter's salary, I'm sure Glenn would be happy to take the money from whatever team will pay it and continue to operate the business remotely as he does now. Of course, maybe you're right and he'd rather get backup pay in the hope that he might then get traded to a team in the east.... somehow I have my doubts.
If he's cut, he gets to decide which offer from which team he takes. He can evaluate the money, the location, the overall situation. If he takes a reduction with Kelly now, then Glenn loses "flexibility" (something Kelly wants to acquire), and Kelly might well do exactly what you suggest... trade him someplace he doesn't prefer. Seems to me this is far more likely to happen to him at a backup salary than at a starter's salary.
If he wants to come east, well I guess Kelly has to make a deal with either Montreal or Toronto for him. Obie doesn't want him and has made other plans. Neither Montreal nor Toronto will pay him starter money. If they do need a backup, then Glenn can get that from them after he's cut, and the team won't have to trade to get him. Unlikely they'll both want him, so they don't need to give up anything in a trade to avoid competition when it's a market of one.
How do you figure the ball is in Glenn's court? He stands pat, does nothing, gets his bonus tomorrow, goes to camp, or gets traded, or gets cut.
It's not a question of the tail wagging the dog, it's just that it's not in Glenn's interest to renegotiate downward ahead of time to make life easier for Kelly. Every time Kelly opens his mouth, Glenn has another new reason not to accommodate him.
I'm sure Glenn doesn't care at all whether he's characterized as the tail, the dog, or anything else. It does seem like it means something to Kelly though....