If Nylander and his agent get too greedy, the Leafs may yet walk away
Photo credit: Toronto Star

Nylander at risk of losing his extension with the Maple Leafs

Published January 5, 2024 at 11:25

There's been a lot of chatter in recent days about a potential William Nylander contract extension in Toronto and not only is it a bit worrisome, given the $11.25M AAV rumours flying around, but it's also a bit exciting to know that Nylander may, in fact, be staying put in Toronto for the next 8 seasons.

The Leafs have put a bit of a timeline on this where they want it to be done, according to reports, and that timeline appears to be ahead of the All-Star break. Some Insiders have suggested that the deal may be done a lot sooner, perhaps as early as the end of this week.

Really, what this team-imposed deadline is about is getting Nylander's number locked in so they know what they can afford to do at the trade deadline in March. The team wants things written in ink a month in advance of the deadline so they know what they're working with as far as the cap is concerned next season. We know it's going up, but what we don't yet know is how much of that excess cap will need to be allocated to Nylander. Once the team knows that, they'll know what they can afford to spend on additional assets.

The reason why this is so important is that the Leafs aren't looking for rentals. They prefer to bring in players with term if they're spending their limited assets. It's not a bad way to go, especially after watching Ryan O'Reilly and Luke Schenn walk away as free agents in the summer when both were originally expected to stay in Toronto.

As far as the negotiations with the Nylander camp are going, Sportsnet's Elliotte Friedman revealed the following during his most recent 32 Thoughts podcast:

"The agent's not talking, but if there was nothing here, the agent would be letting people know, 'there's nothing here'. In my history, that's the way it goes.

The only danger here - because I think everyone wants this done, I think the player wants this done, I think the team wants it done, I think the agent wants it done - the only danger zone here is, does it ever get to a point where, as much as the Leafs have moved, it doesn't get to a space where they can agree and the Leafs just say, 'you know what, we can't go there'.

Again, I have not spoken to the Leafs, so I'm being super careful about this, but I think they feel that they've really budged a lot and now Nylander has to budge a little bit too - and if that happens, this is going to get done. From what I understand right now, there's no reason why this contract shouldn't happen."

The Leafs' original offer to the Nylander camp was believed to be in the $8M-$9M range, while the Nylander camp had countered with something north of $10M. Now, thanks to an outstanding showing through the first half of the season, Nylander's ask is believed to be a lot higher.

According to Friedman, the Leafs have come up significantly with their offer and Nylander is definitely interested in what they're pitching. "They're in the ball-park", as Friedman had put it. Now, it's about Nylander giving a little as well. If he's not willing to bargain, though, this whole thing could fall apart, as Friedman noted.

"Nylander, what he has to look here and say is, alright, how do I get the best possible deal for myself without this getting to a point where the Maple Leafs say 'you know what? we don't like where this is going. It's too much for us and we're not so sure we want to do this anymore.'

I don't think that's what's going to happen, but, to me, that's what Nylander has to stop. He has to know when to say when, before Toronto gets to a point when they're like 'ehh, we're not comfortable with this.' And, again, I think it will get done - we're just in the grind time now."

Obviously, it's nice to hear one of the league's top insiders affirm that this will get done. However, there is some cause for concern, as we have seen in the past that Nylander and his agent, Lewis Gross, are prepared to take things well beyond anyone's comfort zone and haven't necessarily shown a lot of "budge" in past negotiations.

We'll see how this all goes, but with how often Nylander has publicly stated that Toronto is where he wants to be, there's a good chance that the reports are accurate and that this does get done soon.

January 5   |   831 answers
Nylander at risk of losing his extension with the Maple Leafs

Will the Nylander deal happen before the All-Star break?

Yes50160.3 %
No19623.6 %
The team is going to trade him if he's not careful13416.1 %
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