So what your saying is it’s ok for willy and Matthews to sign bigger contracts in five years but we shouldn’t do that with marner.
The problem is it becomes a worse mistake every time you do it, in terms of asset management. You can't prepare for how bad you are going to get dinged on a deal, and because of the uncertainty, of the market and of player expectations, a team can get in some trouble having to create that much new space in a single season. They need to spread the expiry of the deals out. Willie signed for 6 he just didn't show up for the first one
, Matthews was just a bad deal because he got generational front loading with a short term and still stuck them for top dollar. A much worse deal than Willie, but a much more valuable player and more likely to generate an OS. With Mitch, they were expecting to sign the hometown boy for 8 years but in demanding equity with Matthews, that would include the same stupid short term and of course the same front loading. If Marner signs for 4 or 6-7-8 that gives the club more time to absorb the costs and make the necessary changes. Willies deal was an overpay and he should have sat out, but KD would have been a pariah if the Leafs didn't win a Cup. Matthews deal, I don't know, but they obviously smelled blood after the Nylander debacle,
The clubs goal is to maximize the talent on the team, not to maximize the players earning opportunities. The players don't have to give money back after a bad year, and teams are heavily penalized for trying to get out from under bad deals, plus the cap system allows more stable franchises and more player jobs, so the players have a stake in making things work as well. My opinion is, that Marner needing that 5 year deal means he intends to take the club to the cleaners again ASAP to maximize his paycheck(like Matthews), and they already have two of those pricks locked up. Its the downside to waiting to be the third deal in hopes of benefiting from the earlier negotiations. There may not be enough left to give you what you want.