LeBrun: Rival NHL execs on a fair price for a Maple Leafs, William Nylander contract extension

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What better time to catch up on the William Nylander contract situation than after No. 88 capped a trip to his native Sweden in spectacular fashion Sunday?

Some players carry the weight of their unrestricted-free-agent contract year and let it affect their performance. Nylander is clearly not one of those players. He’s on absolute fire, playing as if he’s completely unaffected by what’s on the line this season.

As I talked about on TSN’s Insider Trading on Thursday, it has been mighty quiet on the Nylander contract front, and that’s by design. Both sides in that negotiation have a desire to keep a tight lid on things and have mutually agreed to do so, and that’s what they’ve done so far.

But Leafs fans should not confuse that silence as a red flag. When it comes to the talks themselves, nothing has gone off the rails. My understanding is that the dialogue is ongoing and both sides remain committed to figuring it out between now and July 1.

If either side was getting frustrated, you might be seeing more leaks and message-sending, but that’s not happening so far.

It’s obviously a difficult contract to get done, though, for all the obvious reasons, as the 27-year-old Nylander continues to play spectacularly — one point off the league scoring lead, at 27 points through Sunday — boosting his salary leverage, and the Leafs continue to have a salary cap to navigate.

A lot of rival front offices are curious to see where this extension lands, if indeed the Leafs can get it done, in part because of Toronto already having Auston Matthews at $13.25 million per year starting next season, plus one more season each in 2024-25 for John Tavares at $11 million and Mitch Marner at $10.9 million. And obviously, Toronto needs to be planning for a Marner extension, too, ahead of the 2025-26 season.

So I reached out to team executives in rival front offices across the NHL and asked them a simple question: What do you feel a fair contract extension for Nylander would be?

Here are their answers, via text message, anonymously of course since they cannot publicly comment on player contract negotiations from other organizations:

Note: Some answers are edited lightly for clarity and length.

Team exec No. 1

“This is a very similar situation to Boston with (David) Pastrnak. Pastrnak signed in March (eight years, $11.25 million) of a season he finished with 61 goals and 113 points. So to me, the fair number would be eight years north of $11 million. I know Matthews is at $13.25 million, but only four-year term. If Nylander goes eight years at $11.5 million, that’s $92 million guaranteed dollars where he would have to get over $13 million externally on a 7-year deal to match that money, which is hard to do.”

Team exec No. 2

“I don’t see how it’s less than $11 million, given the rising cap and the season he’s having … unless he wants to take a discount to go to a destination of choice. On a seven- to eight-year deal, that is.”

Team exec No. 3

“My guess is that it comes in around $10.5 to $11 million, depending on the term.”

Team exec No. 4

“Difficult question, Pierre. What is fair and what will happen are two different things (smiley face emoji). He will be 28, has never hit 90 points (although certainly seems he will this season) and has never been past the second round of the playoffs, and only there once. But our system pays on points — rightly or wrongly — and he will have a strong case. Does he help Toronto win more than Matthew Tkachuk at $9.5 million? Probably not. But the cap is going up and Toronto pays a tax premium. $10 million (average annual value), full term. Probably gets more but fair is arbitrary.”

Team exec No. 5

“I start by asking what he would get as an open-market UFA. I doubt anyone goes to $11 million for him, but think he’d get $10 million. So if he wants to stay in Toronto, a bit of a hometown discount might take him to $9 or $9.5 million.”

Team exec No. 6

“Depends on his mindset. Aho (eight years, $9.75 million AAV) is an easy comparable and can be considered fair. But with Toronto’s food chain, he shouldn’t be too far away from what Marner gets next. So that bumps it into $10.5 to $11.5 million territory. He’ll have leverage if he wants it, but if he wanted to keep the core together with 34 and 16, then it shouldn’t be too much more than Aho, who is actually at the top of their food chain. But Aho bought in on a bigger organizational picture and didn’t have a 34, 16 and 91 all making more than him. (Nylander’s) having the right season and a half at the right time. He could cash in, in free agency. Depends if he wants to. If he re-signs, I could see 10.5 to 11.5 million.”

Team exec No. 7

“Nylander is a unique player that you can have a lot of differing opinions on. … As talented as he is, some teams wouldn’t make him ‘the guy’ on their team. A lot of teams see him as the shiny sports car you splurge on when your portfolio is all in order. That being said, players that produce like he does get paid. It only takes one team so I can see a team stepping up in the $10 million dollar range, but it’s likely not going to be a competitive team. I’m not sure how many teams will be looking to make that commitment right now until the cap jumps up more significantly. I’m not sure how Toronto could ever fit him in going forward and still address their holes, but I’ve always had the feeling that he’d remain a Leaf.”

Team exec No. 8

“Somewhere between Gaudreau (seven years, $9.75 million) and Huberdeau (eight years, $10.5 million), I suspect. Has to be south of Pastrnak, doesn’t it?”

Team exec No. 9

“I think fair is in the $10.5 to $10.75 million range.”

Team exec No. 10

“I think because of his age … eight years, $8.5 to $9 million, if I’m the Leafs. They can’t waste Matthews’ prime, so they need him. … How many more prime years are you getting from Nylander? Three? Then are you getting fair value last three or so years? If he wants term, they have to keep the number manageable.”

Team exec No. 11

“Game breaker. Probably count on one hand how many players are as dynamic as him. Can change the game in an instant. At a good age. Not every team has the room but there are 32 teams. Someone will pay it. Below Pastrnak but just. If he wants, it will start with a 10.”

Team exec No. 12

“Eight years, $11.5 million is fair. Touch more than Pastrnak. If you look at internal structure, he should make more than Marner and Tavares. But it will be eight years, $12 or $12.25 million, I would guess.”

My take

What’s fascinating about this exercise is that you’ve got a lot of smart front-office people here with differing views, going from a low of $9 million AAV in one instance to $12.25 million AAV at the other end. What’s also interesting is that everyone who answered has assumed it will be a max-term deal if he re-signs in Toronto, and I’m not sure anyone should 100 percent assume that. Neither side has tipped their hand. Matthews, after all, didn’t sign a max-term deal.

Having said that, the carrot the Leafs have is total dollars over eight years versus going to market and getting seven years max, as team exec No. 1 noted. Mind you, Tkachuk got around that by doing a sign-and-trade on his way out of Calgary to the Florida Panthers to get his eight-year max deal. So there’s always that possibility.

But let’s go back to what we do know: Nylander has expressed a desire to stay in Toronto. Because of that, I do see this getting done with Toronto eventually. I can’t see a max-term deal that doesn’t carry a double-digit AAV, though. Nylander has gone to another level in his game at absolutely the perfect time in his career.

If he wants to also win a championship in Toronto, though, finding a number that works for the Leafs at some level will also be important.

(Photo: Nick Turchiaro / USA Today)

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