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Nylander's eleventh-hour extension with Maple Leafs a win for both sides

The Maple Leafs get one of their core pieces back as they begin a clear pursuit of the Stanley Cup, while William Nylander gets his money on a six-year, $45-million extension in Toronto.

If the Toronto Maple Leafs do indeed win the Stanley Cup in 2018-19, they may very well be able to point to Dec. 1 as the day they put themselves over the top. With William Nylander now in the fold, there is no team in the NHL that has the depth of talent and number of weapons up front the Maple Leafs have. With a Stanley Cup window that is wide open right now, Leafs GM Kyle Dubas likely realized that and knew he needed to have Nylander in the lineup.

So he went out and made a brilliant deal. And looking at the structure of the deal, so did William Nylander. There would have been no winners if Nylander had not signed today. Both Dubas and Nylander would have looked like take-no-prisoners negotiators, but in the end the Leafs would have been without a valuable asset and Nylander would have lost money he would have never made back. By signing the deal the way it is structured, both Dubas and Nylander are winners.

Because by getting an annual average salary of 6.97 million in the final five years of the deal, Dubas gets a manageable number that is not far off what he was offering in the first place. But by structuring it this way, Nylander gets his money.

And here’s why. In Years 2 through six of the deal, Nylander will receive $33 million. In Year 1 of the deal, he receives a $2 million signing bonus and a $10 million base salary. But because he sat out the first 59 days of the 186-day season, he’ll receive $6,827,957 of that total. So if you total the actual money he receives over the six-year period, it comes to $43,827,957, which equates to an average of $7.3 million per year. Considering the Leafs were coming in a $6.5 million and Nylander wanted $8 million, that’s basically right in the middle. Nylander wins in that the Leafs bought only one year of unrestricted free agency on the deal, plus he got lockout protection in the form of $3.5 million signing bonuses in each of the final five years of the deal.

So Nylander will make just over $8.8 million this season and of the $9 million he receives next season, $8.3 million of it is in signing bonus. So that means in the space of the next seven months, Nylander will receive more than $17.1 million dollars, meaning the William Nylander Tag Day has been cancelled.

And it was incredibly important for both sides to come out of this in a positive light. Dubas is a rookie GM who had decided to dig his heels in on the Nylander contract and he couldn’t afford to cave, particularly with the Auston Matthews and Mitch Marner deals on the horizon. Nylander, on the other hand, took an enormous risk in using the only leverage he had, which was to withhold his services. There was no way he was going to come back after sitting out the first two months of the season to a contract that had the optics of being too team friendly.

Chances are, Nylander will not be in a Maple Leafs uniform when this deal expires after the 2023-24 season. The only season he could have received a no-trade or no-movement provision would have been in the last year of this deal. And once the Maple Leafs sort everything out and they allocate their cap space to all of their young stars, somebody is going to be left out. Whether it’s Jake Gardiner or Nylander or someone else, the Maple Leafs won’t be able to fit everybody under the salary cap.

And that’s apparently the way all of this was supposed to work when the owners shut the game down for a year to get cost certainty. We’ll see how much some of those same owners like it this summer when the best group of players in NHL history comes out of its entry-level deals simultaneously, but this was the system they wanted. As for the Maple Leafs, they can go about the task of trying to win their first Stanley Cup in 52 years with another powerful asset in their lineup.

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