The William Nylander situation has taught us that contract negotiations are anything but easy, and are unlikely to leave any of us feeling happy about the outcome. Such is the issue with having star players, something the Leafs haven’t really had to deal with in the salary cap era. Sure they had Mats Sundin as he steered into retirement (and Vancouver) and they had Kessel, who had the luxury of really being the only worthwhile star on the team, and getting the contract he wanted, but now the Leafs are in a very different situation than they’ve been in for over the past decade. They have players they want to re-sign, and those players can name their price.

Whatever you think of the Nylander contract situation, it’s his right to do what he’s doing. He’s not a holdout, he doesn’t owe it to anyone to sign, and in fact he’s very clearly the one who is currently suffering the most by not getting a deal done. He’s the one not being paid, he’s the one who is not playing, the Leafs are winning and for the time being they are doing just fine without him. That said, Nylander doesn’t feel he’s received an offer that he’s comfortable accepting. A poor example of that is all of us. If you feel you are worth $80k a year, are you readily willing to take a $70k/yr job?

If you’re out of work, yes, probably, but you’re probably still looking at your other options. Since hockey players don’t really have a lot of options beyond negotiating a new contract within the NHL, it reasonable to assume that players will fight for every last penny they can. And I hate to be this guy, but there’s a pretty big difference between making $7.5M a year and making $7M a year. Plenty of people would sell their souls for a salary that would pay them that gap.

Yes. Sorry. The point is that right now there is a lot of frustration with the way things are going with Nylander, and I’d argue that this is the new normal and we can expect challenging negotiations with Matthews and Marner as well.

We lie to ourselves into believing that playing in Toronto is something special (it isn’t to everyone).
We lie to ourselves that players should take a discount to stay with their club, and this is particularly ridiculous when you consider these players had no choice over where they would be drafted to, and honestly, why should Matthews have to take a discount to cover off the Leafs mistake in signing Nikita Zaitsev?
We lie to ourselves that we understand the motives of individuals because of a few flippant remarks that find their way into the paper. We really know how much Matthews loves living in Toronto or how much he enjoys when he gets to play in Arizona, but because he’s going to answer those questions positively like all good hockey boys, it sure looks like those are the only two teams in his heart.

Yeah. Auston Matthews wants five years. That five year ask sets Auston up to be an unrestricted free agent when the deal is done. Most importantly, a five year deal is different than a seven or eight long term deal or a two/three year bridge deal, so no one seems to know how to react.

Personally, I don’t know why we haven’t seen more of this. For the star players who expect they will be playing up until they approach forty years old, it seems like good business to maximize salary and minimize term up until they turn 30 and then will be forced to crave the job security the rest of the league seeks on regular basis. Unless you are frightened about career ending injuries, which are a very reasonable thing to be frightened about, gambling on the shorter term seems to be worthwhile.

Matthews hasn’t been secretive about knowing that he has value. He decided against playing in junior or college and instead chose to play his draft year in the Swiss league, where he could draw a salary. He’s had no problem taking advantage of the endorsement opportunities available to him by being the star player on the Maple Leafs, and where a short time ago many would have scoffed at the idea of Matthews making near McDavid’s salary, it seems almost a given that he’ll get paid very similarly come next season. All of this is fair. He’s very good, it’s just unfortunate that it doesn’t benefit the Leafs.

While a discount to play in Toronto sounds nice, it’s harder to make that sound reasonable when the team is owned by Bell and Rogers, and digging into their deep pockets won’t keep me up at night. As much as we all want rosy salary cap picture, Matthews in no way owes it to the Leafs.

Well…we’ll reach a little on this, but if there’s one it’s this, anytime someone makes a demand for something they want in a negotiation, you’ve provided the other party something they can leverage. Perhaps this shaves a bit of money off the contract ask. Perhaps the Leafs can drop his salary in the lockout seasons, and get a bit of space back that way. The Leafs also get Auston Matthews, and that’s not really something that can be understated. The Leafs preserving Tavares and Matthews for 5 more years together isn’t nothing. Even if that means making a tough choice on Marner or Nylander, having Matthews around has to be the priority.

At the end of the day, any new rumour or speculation about Matthews, Marner, or Nylander just reaffirms what we’ve known all along, it’s not going to be easy to keep them all and none of them will be cheap. Up until the Nylander situation we had the luxury of lying to ourselves about how the Leafs could figure out a way to do this with little pain involved, but perhaps we forgot that these players know how good they are. When we consider a few short years ago the Leafs were giving similar % of the salary cap paydays to Dion Phaneuf and David Clarkson, this doesn’t seem like a bad situation.