Maybe it’s Dubas, not Nylander, that’s the nightmare negotiator

Yes, it’s another Nylander contract article. And before we get into it, let’s establish something: Darren Dreger doesn’t really know anything about the Leafs and is sad because this new management group doesn’t feed him information like Nonis did, so his “Nylander is looking for Draisatl money” claims are likely trash. It’s perhaps best to completely ignore them.

The more realistic scenario is that Nylander is looking for David Pastrnak money, around $6.67-million annually, with a slight uptick since the cap has grown a little since last year. That ask would be totally reasonable. And you know what? While that does seem like fair number for those of us viewing from the outside, I think the Leafs don’t want to give it to him. Like, at all.

That’s right, maybe the toughest negotiator here isn’t Lewis Gross or Michael Nylander or whoever else we’re told to blame for this stalemate. Maybe it’s been overlooked that Dubas could be an extremely difficult negotiator, mainly because he’s so young and still relatively inexperienced at the pro level. He seems so friendly, how could he be a shark?

But Dubas did just spend three years learning from perhaps the least player-friendly general manager there’s ever been in Lou Lamoriello. It shouldn’t be entirely unexpected that he’s the one putting the squeeze on in this scenario.

This process of negotiating Nylander’s contract doesn’t just exist in a vacuum. It’s a domino in a line with Marner and Matthews getting their own new deals within the next twelve months. Hard-balling Nylander now and eventually locking him in to $6.0-million (Nikolaj Ehlers territory) a couple weeks from now instead of rushing into $6.7-million over the past summer, for instance, obviously saves the Leafs $700K per year on that deal, but then that likely cascades into savings on Marner and Matthews. Let’s say that’s another $500-700K on each of those, for the sake of a number. Now you’ve grinded out around $2-million dollars in cap space.

I realize I’m probably oversimplifying here, but this is how these negotiations have to go, and likely how the Leafs see things playing out. And, I mean, it is a simple process at its core: Save money now by pushing hard on Nylander, letting him sit games, and you have extra money to spend elsewhere years from now.

Dubas is a smart guy, and without question he sees things a few moves down the line. But as this story continues to unfold and people get a little more panicky, the focus on Nylander gets more and more critical. His agent gets a rep for being a particularly difficult negotiator, but really, is he? His other big client, Johnny Gaudreau, went to the wire and nearly missed games to get a new deal with the Flames, but that contract did turn out to be quite team-friendly.

No, I think it’s just as possible the Leafs are the ones anchoring things down in this situation, especially given some of Shanahan’s comments on the core taking discounts to keep things together. Maybe I’m speaking for myself a bit too much, but it seems we’ve gotten spun into thinking Nylander is looking for a boatload of money and the Pastrnak comparable is what’s right. For the team, that might not be the case. For all we know, that Pastrnak number is a bridge much too far. Again, Dubas did just spend years learning from a guy who isn’t exactly known for buckling to player or agent demands, and has historically done anything and everything to get the slightest of edges in working out contracts.