William Nylander is on pace for career-best numbers and the timing couldn’t be better for him.William Nylander is on pace for career-best numbers and the timing couldn’t be better for him.

Nylander is on pace for career-best numbers and the timing couldn’t be better for him — he’s eligible for a contract negotiation as early as July 1.

By Nick KypreosContributing Columnist

Thu., Dec. 15, 20225 min. read

It’s been a frustrating battle at times for Maple Leafs fans watching William Nylander over the last seven seasons. But it all seems to be coming together this year.

It’s as if the stars aligned.

“He can and should be in that top elite tier of players in the league, and he’s working his way there,” Leafs coach Sheldon Keefe said after Nylander’s five-point night on Saturday.

We now watch a confident, stronger and more resilient player who has consistently brought the Leafs’ threat of winning against top-ranked teams to a whole new level.

Nylander is on pace for career-best numbers and the timing couldn’t be better for him. Leafs Nation, sorry to be the one to bring it up but Nylander is eligible for a contract negotiation as early as July 1 — no different than your record-breaking stud Auston Matthews.

So the question needs to be asked: Why has there been little to no mention of a Nylander contract extension that, timing-wise at least, mirrors Matthews?

Clearly the major difference between both players is the attention their future has warranted up to this point. The chatter regarding one player has hit a feverish pace, especially this past off-season, while the other is as quiet as a church mouse. Well, at least until now.

I can hear many readers wondering aloud: “How come we can’t get through a season without Kypreos mentioning money?” It’s simple, really. When the level of play jumps like Nylander’s has, so do the terms of a new contract and pressure on the team to try to keep the player long-term.

In the case of the Leafs, it may also stress the importance of winning the Stanley Cup this season.

As the board of governors meetings concluded this week, it’s no secret that both NHL commissioner Gary Bettman and major market owners like Toronto would love to see the salary cap raised as quickly as possible. They are tired of seeing good quality players being forced out.

But here’s the issue: Bettman needs a healthy NHLPA to negotiate with and they currently have no active executive director. Yes, Donald Fehr is still there but in name only. He has been relieved of his active duties, so to negotiate an artificial salary increase in the near future seems highly unlikely.

Whatever the salary cap looks like for the next two seasons, it doesn’t seem to support being able to keep the Leafs’ big five (Nylander, Matthews, Mitch Marner, John Tavares and Morgan Rielly) intact beyond that.

Even though the Leafs will only have $31.5 million by 2024-25 committed to Marner, Rielly, Tavares and Calle Järnkrok, it’s conceivable that by the time you factor in Matthews and Nylander extensions it leaves Toronto with just over $30 million for the remaining 16 players, including one starting goalie on a projected $88 million salary cap. That’s what pro hockey players refer to as the crumbs.

So while many have projected Matthews to take 16 to 18 per cent of the Leafs’ cap space on his next deal, meaning a $14.5-million to $15-million average, I have yet to hear projections on what Nylander might get.

Comparables around the league are always a good place to start for general managers. If Nylander maintains a mid-30 goal season, he’s in the ballpark of Nashville’s Filip Forsberg, who recently signed an eight-year deal with an annual average value (AAV) of $8.5 million.

But Nylander’s skillset and newly minted elite status, in my opinion, lands him closer to Rangers star Artemi Panarin, who makes $11.6 million a season, and pending Bruins unrestricted free agent David Pastrňák.

So here is the burning question: Can the Leafs afford to take Nylander’s deal north of $10 million this summer? If they feel they can’t, it’s possible they would rather trade him in the off-season than risk him playing out the final year of his contract. Of course, there’s always a chance the Leafs can convince Nylander to stay for less than market value simply because “he likes it here.”

That is the hope for Bruins management and their fans as they are in the midst of heavy negotiation with Pastrňák. They, too, are praying for a team-friendly discount. But I can report with confidence that as of today, it ain’t working.

The good news for Leafs fans this season is every high-priced player the team signed out of their entry-level deals has proven their worth. Two seasons in a row we’ve seen major franchise records broken and fans enjoying the ride off the backs of Matthews and Marner. And while the disappointment of six straight first-round playoff exits is part of the package, Leafs Nation can still say they’re worth every damn penny.

It took some time to see the real value in Kyle Dubas’ now-infamous “we can and we will” signings of all his young talent. But the new sticker prices we see on July 1 will be even higher — with or without a first-round playoff win.

Kyper’s Korner

Speaking of Pastrňák, the Bruins would dearly love to get him as close to Charlie McAvoy’s $9.5-million AAV as possible, but the feeling is he has his eye on raising the bar from Panarin’s $11.6-million cap hit in New York. … “He really wants to win and that’s his No. 1 priority. The fact that he wanted to stay with us shows he believes in the organization. He loves the city.” That was Steve Yzerman — then Tampa Bay’s GM — talking about free agent Steven Stamkos back in 2016. Well, it’s starting to feel like a similar negotiation is expected between Yzerman, now the Red Wings GM, and hometown hero and pending UFA captain Dylan Larkin in the hopes of once again convincing a star to settle for less than market value. … Another sign of the salary cap crunch: the Seattle Kraken were the only team to put a waiver claim on Nashville’s 2017 first-round pick Eeli Tolvanen. Some teams tell me they didn’t want to commit to his $1.45-million contract next season. … Eyebrows are being raised around hockey-related-revenue beancounters with regards to the Winnipeg Jets’ inability to sell out games. Tuesday night’s marquee matchup against the Vegas Golden Knights drew their lowest attendance of the year at 13,102.

Change my mind

Anaheim head coach Dallas Eakins won’t finish out the season. I hate to say it, but his players showed the type of effort that gets coaches fired during Tuesday night’s game versus Toronto.

Nick Kypreos is a former NHL player, Stanley Cup champion and current host of Sportsnet’s Real Kyper and Bourne radio show. He is a freelance contributing columnist for the Star and is based in Toronto. Follow him on Twitter: @RealKyper

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