Matthews is not going to be as open and shut to re-sign as some of the optimists in here think. After next season he has ALL the leverage to get paid whatever he wants and Dubas, or whoever the GM is at this time next year, will have no choice but to give him a massive deal that sets the new bar in the league, or trade him if he's not going to take that money.
If the Leafs flame out in the 1st round next year Dubas, Keefe, maybe even Shanny will be gone: job not well done, utter failure, disgrace. Will Matthews have any loyalty to the new management team? Even if he does, will he want to leave for a fresh start elsewhere, somewhere he'll be given the captaincy as the undisputed leader of the team?
If there's even a hint of him not accepting a multi year extension next off season, you absolutely HAVE to deal him. You can't go into the season hoping a long term, or even shorter term deal, can be worked out once the season starts. You can't even trade him once the season starts due to the unprecedented NTC he got on top of his high salary and short term deal.
You can't wait until the following season only to hear him say he wants to live elsewhere due to "family", wanting to live in the states due to Covid restrictions, personal privacy, mental health or blah blah blah like that.
His only loyalties in Toronto are to his teammates and maybe justin Beiber. They're all rich mofos like him and they'll all support him not matter what he does and if he wants to live closer to family, he's gone.