Edmonton has been as close as you can get the past 2 years but it remains a challenge to see them do it again as this team continues to age out. The pressure on Howard and Savioe to show they can be something is pretty big as I can see McDavid looking at a roster of him and Draisaitl at 30+ and a bunch of other older vets.
I still think it is a 2 year extension he will end up signing. If he wanted to chase rings though signing in a place like San Jose next summer where the team has young stars, cap space and assets to make moves to win immediately makes sense as well or a team like Carolina who have everything but the superstar
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