Nylander impasse start of more Leaf headaches

Numbers in this deal are strongly linked to future contracts for other Toronto stars

William Nylander may be stubborn and unmoving in his contract snafu with the Toronto Maple Leafs but he’s not necessarily wrong.

Kyle Dubas, the first-year Leafs general manager, may be stubborn and unmoving in this dispute with Nylander, but he and the Maple Leafs may not necessarily be wrong in how they have proceeded to date in this growing stalemate with young Nylander.

And therein is the real difficulty of this contract conundrum for the Leafs.

There is not necessarily a bad guy here. There is not necessarily a side acting inappropriately. If you listen hard enough to either side, and both aren’t saying much, there is no one being terribly unreasonable.

But there are two opinions, absolutely wide apart, getting no closer to conclusion, and no one yet seems willing to blink first. Someone will have to blink for this to eventually end.

The Leafs have looked to sign Nylander for somewhere between $6 million and

$7 million a year, long-term, money ranging somewhere between $42 million and $56 million over the length of however long the deal will be. Life changing money for Nylander and his family and if the money is handled intelligently and properly over the next eight years, it will be life altering money for Nylander now and for his family long after he is gone.

So how do you say no to that? That’s what the Leafs are wondering, watching this team score at will in the early season, missing Nylander’s skill but not missing a beat it seems offensively.

There’s no real pressure point as a Dec. 1 deadline approaches: the pressure when November begins shifts sharply in the direction of Nylander.

Nylander is looking for at least $8 million a season. On the surface, that seems like a reach. But bigger picture, over a possible seven-year term, that’s about a $7-million difference from what he wants and what the Leafs will eventually sign him for.

Half of that goes to taxes in a tax-heavy country which is a difference, over the length of this fictitious seven-year deal.

Will Nylander’s life change if he makes $45.5 million, for example, instead of $49 million, with another contract to sign after this one? This may be difficult to explain to a 22-year-old with confidence and a belief in his skill set. This may be difficult to comprehend for an agent working hard for his three per cent. But in a more global view, it’s something Nylander should probably consider.

Here’s the personal part for Nylander or anyone else in his kind of situation. You have to live with the deal you sign. You may love it on the day you put pen to paper — Nikita Kucherov did that with his bridge deal in Tampa Bay and then wound up resenting it — but if Nylander signs somewhere below $7 million a year, the dynamic in the Maple Leafs dressing room may be challenged in the future.

This is part of the personal difficulty for Nylander and the Leafs.

The Leafs have a template of some kind sitting on assistant GM Brandon Pridham’s desk, projecting future salaries and future salary cap levels not just for next season and the year after but for years to come. After the Nylander negotiation there are deals to be made with Mitch Marner and Auston Matthews. Each deal, in a way, affects the others.

And if you’re Nylander and you sign long-term at $6.8 million, for example, which is above market value for him under today’s salary structure in the NHL, how do you feel when Marner signs for $9 million a year next season — these numbers are assumed and estimated — or Matthews comes in above John Tavares at around $12 million in the future?

The question becomes: can Nylander live in an NHL climate surrounded by players he considers to be somewhat equals making significantly more money than him? That would gnaw at some. Others would be secure enough to not let it bother him.

We don’t know how this will end or when. This isn’t a holdout. You can’t holdout from a contract that isn’t signed.

This is a stalemate. Two separate islands and as of Thursday afternoon, no one was moving in any direction at all.