Still think it's funny that they could have had Marner signed for $9 mill per for 8 seasons if they had signed the extension during the summer. Leafs thought it was too steep. The Sportsnet panel stated that about a a month or two ago.
That's where you have to decide risk/reward with your young core players. One of the only good things Chiarelli did in Edmonton was bite the bullet and give Draisaitl 8.5 to ensure he got max 8 years on the contract. He could have bridged instead and then he'd be paying for a guy with a 50g 100P season under his belt with a rising precedent for contracts of young star players. In all honesty, the leafs were a bit unlucky that their young star players came in when they did because expansion teams and the McDavid+Eichel /Toews+Kane contracts changed the climate for NHL contracts.
I do think that they made a mistake with the Matthews contract. It's fine that they overpaid on the AAV as of today because sometimes those gambles are worth it with young players betting on their potential. The problem is they only got 5 years on it, and at the same time they had another young player in Marner outperform Matthews this season during his contract year. They should have been progressive thinking and signed him in the summer at an overpay for what he had shown, while betting on his potential given the direction that contracts are going for star players. It's impossible to know though what they thought of his potential. If they thought he'd become what he was this season then they definitely messed up. If they didn't then I can understand why they didn't want to give him that contract. If they waited because they thought he would eventually cave because he's a good ol' Toronto boy, well then Dubas is in over his head further than I thought.