Leafs made Nylander contract extension a no-brainer

They could have had their star for less if they had signed him earlier. But after Nylander made it impossible for them not to, the Leafs gave him everything he wanted. Because that's what they do

Right about now, there’s a tendency for a lot of people to think William Nylander is overpaid. It’s wrong, of course, because Nylander is among the best in the world at what he does and is lucky enough to do it in a multi-billion dollar business where a lot of people are making money. He had every right to ask for, and receive, what he’s getting. As much as people can’t understand why hockey players get so much to play a game they’ve loved since they were kids, the reality is that elite NHL players are paid a pittance compared to their brethren in other professional sports.

And every bit as much as teammates Auston Matthews, Mitch Marner and John Tavares, Nylander had the right to demand that all his contract demands be met. When his eight-year, $92 million extension kicks in next season, his average annual salary will be slightly more than what Marner and Tavares are receiving on contracts they signed years ago, and he’ll be well below the $13.25 million Matthews will be making when his four-year extension begins in 2024-25. The salary cap is going up and Tavares’ contract will be on the books for only one more season.

When you look at it objectively, there’s absolutely nothing wrong with this contract. So why does it seem like there’s everything wrong with this contract?

Well, like a lot of other things, it’s complicated. One of the reasons is both sides framed this as a negotiation. Well, it really wasn’t, judging by the terms, because Nylander laid out exactly what he needed in order to stay in Toronto and the Leafs capitulated on every single demand. If there is supposed to be give and take in a negotiation, where exactly was the give on the Nylander side and the take for the Leafs’ camp? Nylander wanted a lot of money on a maximum-term contract. And he got both term and dollars. He got a ton of money, $69 million, in signing bonus. He got a full no-move clause. What, if anything, did Nylander give up to stay in a place that he made no secret was his first choice? In reality, the Leafs could have had Gino from Woodbridge doing the negotiations instead of a seasoned pro such as Brad Treliving and it would have yielded the same results.

“It was a really smooth process from start to finish,” Nylander told reporters after signing the deal. Of course it was, because it always is with the Leafs and their stars.

This for a player they were unwilling to go above $9 million on an eight-year deal just a few months ago. Had they offered $10 million a year over eight years during the off-season, there’s a good chance they get this deal done. But instead of sputtering and being distracted in a contract year, Nylander went out and had the half-season of his life. Sometimes these things work out. Sometimes they don’t.

But the bigger picture here is that the Maple Leafs fancy themselves as an iconic NHL franchise. Anyone born after 1970 might wonder what this organization has ever done to have such a high opinion of itself, but there’s no doubt it leans heavily on its long tradition and illustrious past, even though you need a high-powered telescope to see it. So it begs the question, if the Leafs are so powerful and attractive, why do they always have to back a Brink’s truck up to a player’s house in order to get him there or keep him there?

It's real swell that the Leafs can get Mark Giordano to sign a one-year deal worth $800,000. But when it comes to their stars, why can’t they ever seem to do what the Pittsburgh Penguins have done with Sidney Crosby and Evgeni Malkin, or the Chicago Blackhawks with Patrick Kane and Jonathan Toews or the Boston Bruins with Patrice Bergeron and Brad Marchand or the Tampa Bay Lightning with Nikita Kucherov and Steven Stamkos and Andrei Vasilevskiy and Brayden Point?

Why have the Maple Leafs never been able to create the culture that team president Brendan Shanahan talked about years ago? You know, the one where players are willing to take a little less to keep a good thing going, they way those unselfish guys did in Detroit in the days before the salary cap.

Well, you’ll notice that all those other teams I mentioned previously have won a Stanley Cup with those players. What can the Leafs offer when it comes to a winning environment? “Hey, guys, stick around and maybe someday we’ll win two playoff rounds.” It’s difficult to attract guys to a winning culture when, in reality, you haven’t created one. This team may win something someday rather than come close to almost winning something like it often does, but that hasn’t happened.

Toronto doesn’t have the winter weather that places such as California and Florida do, but for heaven’s sake, the Winnipeg Jets were able convince Mark Scheifele and Connor Hellebuyck to sign eight-year contract extensions with minimal drama, so it can’t be that factor that makes the Leafs so willingly open their wallet.

So, it must be the unbearable pressure of playing in “this market.” Yup, that’s got to be it. It’s just so damned difficult to play in a place where the fan base is so rabid and unpredictable and the media is so incessantly intrusive and opinionated. Because guys who play for the Dallas Cowboys, New York Yankees, Los Angeles Lakers, Manchester United or Bayern Munich never have to deal with that stuff. Players on the Leafs are actually the subjects of unconditional love about 90 percent of the time and, like athletes in every other market, are so well insulated from the white noise by their organizations that it’s manageable and possible to function at a high level.

After Tavares signed his seven-year, $77 million deal in the summer of 2018, he put out a picture on social media of him as a kid sleeping in Maple Leafs pajamas wrapped in Maple Leaf bedsheets. You can bet he didn’t show that to the Leafs during the negotiations. After signing his deal, Nylander said, “This is home. From my own choice, I wanted to be here.”

You can’t really blame him. Why would anyone ever want to leave a place where they always get everything they want?