I think his trade demands come if/when Matthews beats him in a scoring race and starts pulling major endorsements away from McDavid.
His team won't like that.
They will also know there is a 0.01% chance of a regime change in Edmonton. Even if there was, the cap management is so poor it won't happen, leaving the trade request as next item.
I suspect it will come early next summer. It will start with leaked demands that the team surround him with better players and then when that doesn't happen there will be a trade request.
What is McDavid worth if traded?
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