Tough question. As a fan, who isn't being paid millions of dollars to make the best of hard decisions, I'd love to say, "just trade him" but it's not that easy. If I were Treliving, I'd be asking myself these questions:
1. What is the max number (and least term) I feel we could pay Auston without being forced to move a key contributor like Willie or Mitch?
2. How would conceding to Matthews impact requests from Nylander and Marner? Knowing if they don't both cave, one or both would likely be cap casualties.
3. How would the team fare if Matthews ended up the only superstar and I had to surround him with depth instead of multiple high-end pieces?
4. Is Auston Matthews the type of person, leader, or personality who will sacrifice, scratch, claw, and bleed for a Cup? If he won't even sacrifice a few bucks, is he willing to sacrifice his health, quality of life, or mental discomfort to battle for Cups?
My quick answers to those questions are:
1. 13.25 x 6. Max.
2. Nylander may need to be traded immediately. If not, Marner will be this time next year.
3. Recipe for disaster. We saw this with Sundin for years.
4. If Matthews isn't willing to budge and give us a hometown discount, then I am convinced he's selfish, spoiled, and not the kind of leader who will sacrifice when the playoffs become nasty.
Then I would go to the MLSE board and tell them my thoughts and ask which they prioritize more: star power and gate receipts or a shot at winning a Cup?
Based on the answers from my bosses, I'd maneuver accordingly.