I don't get the thinking that Matthews is practically out the door in two years. If they make the playoffs both years and get out of the first round, I can see him wanting to stay a Leaf.
Honestly, the wildcard here is goaltending. AA is showing some real progress in the Marlies playoff run ... they look to have a better-than-average tandem going forward. You never know, if the goalies go on a heater they might actually find their way to the SCF.
Every season, every team has some sort of a shot at a Cup. Maybe it is as low as a million to 1 but ...
He has all star selections, Calder, Hart, Richard, Lindsay trophies
Olympic gold, junior gold, Swiss Championship
Leafs scoring records. American scoring records
He'd probably like to add a World Championship
But the big thing missing from his resume is a Stanley Cup
He might be watching his buddy Mitch skating around with a Cup over his head and maybe a Conn Smythe under his arm in the next couple of weeks ....
If Matthews can win a Cup, he's a shoe-in for the HHoF (if he isn't already)
Ideally, he'd like to win one while he is a key contributor. Leafs can't likely offer him that - they're well past their best-before-date and the rebuild will take too long. Like Mitch, he's very likely going to have to go elsewhere if he wants a Cup ring. That is what his agent and advisors are going to be telling him. And the lure of US tax breaks ..
He won't make any noise about that until it is time to do so. That will hold the media at bay. I'm sure he doesn't want to go through the circus Marner did but we'll probably know within a year or so - after next season is over so he doesn't have to get hassled by the media incessantly. Hopefully, they'll get more than a 4th line center. I'd love to be wrong but I do not see him finishing his career here.