I would be pretty annoyed as a Leafs fan. In a cap league, you can't win when your star players squeeze every penny they can out of management. He deserves the AAV on paper, but it just doesn't leave you with enough room to improve the rest of the roster.
I'd assume the 3 years stuff is bullshit. The AAV also seems suspect...
Unfortunately the salary structure for the team has been messed up since Matthews and Marner got their contracts (and they signed JT.) Not only did Dubas mess up dollar and term, but he signed them at the worst times possible (Matthews before Marner, neither guy the summer before their breakout seasons, etc.) He even ruined Nylander for a year, which is funny because Nylander's ask was the closest to being fair. Shanahan shares the blame for letting it all happen.
At this point they're handcuffed by Matthews, Marner, and now even Nylander. Nylander wants to be overpaid like Mathews and Marner were, and considering he made significantly less he has good reason. Marner is going to ask for the moon after a cap increase, and Matthews knows the team won't just walk away.
Nylander is the guy who deserves the least to get moved but probably will to accommodate Matthews and Marner. Whatever, it is what it is at this point. The Leafs need to draw a line going forward with every player not named Matthews and Marner. Maybe they get lucky with a couple young cheap guys and salvage things with a rising cap.