Welcome back my Salary Cap-friendlies! This being an article centered around all things salary cap, I've had it on my docket for some time that eventually I would write something about William Nylander. I'd avoided it for a while given that it seemed like every time, he was up at the podium during preseason he would get asked about it, but now is as good as time as ever as his play and looming free agency has dominated the NHL new cycle. That's either because most of the NHL shows I listen to are an hour long and talk about the Leafs for 57 minutes of that hour or I have Toronto in my points pool. Could be a mix of both, there's really no way of knowing for sure.

It seems like every time the Nylander contract subject comes up, it's like his next contract has gone up another million dollars. This only got louder during the NHL Global Games in Sweden where he really played well. I know that it's November but for now maybe we can piece together what a contract could look like, when it's potentially signed, and who it's signed with. Don't panic, I'm saying Leafs unless things go really wrong come playoffs…which…not touching that subject. I'm in a good place right now. Also, worth mentioning before we dive in here a trade is highly, highly unlikely. Nylander's contract has a M-NTC that kicked in this season, and I'd have a hard time believing that even with the haul the Leafs could get back in return if Nylander was not going to re-sign, that they would make any sort of trade.

With that in mind, I think first we need to revisit the contract that Nylander signed five seasons ago, which in going back and looking at how the NHL landscape was around that time is like going back and watching Foster Hewitt call games in grainy black and white picture. I remember the trade rumors that summer swirling that Toronto was going to look to trade Nylander, but I had forgotten just who the potential dance partners were. Remember when Corey Perry got hurt for Anaheim? Of course not, but it happened and recall reading speculation of a Nylander sign-and-trade to the Ducks. This was a real thing you guys, I'm not making this up! What we do all remember though is Nylander holding out…and holding out…missing training camp…and then ultimately missing games. I was worried with the way this was all playing out because out of the contracts that needed to be signed for Toronto, I had thought that they were handled in reverse order, but nevertheless a deal broke through and off the bat I thought it was a good deal and it was what had been reported all along going back to that summer. Four years, $41M. Oh I forgot something, the contract had a $2M signing bonus. Okay cool sure. That went along with the $10.2M cap hit. Alright, so a pay day here but what happened July 1^st? That would be that his signing bonus on the second year of his contract jumped all the way up to a cool $8.3M for that season and that season only. I can hardly get a cost-of-living increase at work, I need to talk to Nylander's representation at the time because in seven short months, he had made over $20M. 

I'm going back and referencing this because I think it's important on what could possibly happen here in the future. Let's start with at the bottom and work our way up, do I think there's a holdout like we saw last time? I'm going to say no I don't and I'm going to bring in another player for reference here and that's Gabriel Landeskog. Landeskog wasn't in the same realm of cap space for that Colorado club like Toronto is now, but he did sign right as he was playing really his best hockey in his career before winning the Stanley Cup in 2022. What happened next? Anyone rostering him in fantasy this season? Unfortunately, no. Injuries happen, and we haven't seen him on the ice yet this season but the point being he came up for free agency at the time of his career where he was playing his best hockey and didn't mess about here. I've seen more and more players since that time sign big (and I mean really big) when their best NHL career comes on the eve of their free agency summer, and I think part of it is two-fold. It's sometimes better to get one large check on July 1^st, and you just never know what way your career might go if you, "bet on yourself" so to speak. At 27, Nylander could opt for a shorter term high AAV, but I do think there's a world and situation in Toronto where this might just be the time to get that larger contract. Another reason I just cannot foresee a holdout is because by the time NHL training camps are through, most clubs have their final rosters set with the high-end cap space clubs being the ones that are likely at the bottom of the standings working to get to the cap floor, or clubs with around $3-$5M available. If he's looking to get what we all believe will be near or above the $10M mark, holding out wouldn't make much sense here.

So say he opts into free agency, what would that look like? Easy enough to guess, he'd want to go to a contender which is what is on everyone's free agency BINGO card but again a holdout does him no good given just how much he would demand. I know in free agency we often look at the Provincial tax rates and if anyone wants to know if he signs at $11M the total tax after income would look like $5.1M. Look, that's tough but it hasn't stopped players from signing in Toronto, or any province, before. Example, how about three of his teammates? This is the reason I don't think he'll reach July 1^st; Toronto is going to overload this contract with signing bonuses galore. Yes, Nashville, Florida, and Dallas all play in places with no state income tax but those teams do not have the same resources that Toronto does. We can talk all we want about revenue sharing in the NHL and how the cap makes things an equal playing field, but it does not, otherwise we would have seen John Tavares in a San Jose Sharks sweater. Plus, for the state income tax argument it is valid but all I can say is that for example I live in Illinois (sad), and here everyone knows someone who has moved to Tennessee for one reason or another and in part because TN has no state income tax. Great right? Well sure but each state (and I would guess Provence) gets you one way or another. No state income tax in Tennessee, but the highest sales tax in the country at an average of 9.5%.

I'm going to lean here that Nylander does not venture into the free agency waters so what would a contract look like and how does it impact the Leafs? $10M, makes it harder for the club, $10.5M even more than that, you get the idea. I really think if I'm looking at comparable contracts to what we could see him sign at, that I'm looking at another player who cashed in at/around the same age as Nylander at an AAV of probably close to $11M. Lucky for us we have the perfect comparable as David Pastrnak signed a similar contract this past offseason which includes (as every contract does now) full NMC, M-NTC, at a grand total of 8YRx$90M. Only I think what we could see here would be signing bonuses closer to what Nylander's teammate Auston Matthews got, and that could hit close to or over $10M while the highest signing bonus Pastrnak will receive is $4.5M. Again, Toronto is on a different plane than everyone else.

Let's say that it is $11M next season, what does the Toronto roster look like? Honestly not as bad as you might think it does. I'd venture to guess that next this summer, the Leafs will have around $30M in cap space. Let's say Nylander takes $11M of that, we're looking at $19M available and I think there's a very real roadmap to where the Leafs make similar signings that they did last offseason but much lower. Right now, and coming off the cap, would anyone be upset with losing Tyler Burtuzzi ($5.5M), Ty Domi ($3M), TJ Brodie ($5M), and John Klingberg ($5M)? I didn't think so, and as much as I'd say that all GM's spend to the cap ceiling, I just can't see 1-yr deals like these coming onto their books going off what we've seen so far unless things drastically change. I also think it's in Nylander's favor that it's really only him and him alone that the Leafs are working with unless Ilya Samsonov makes big strides the rest of this season. You're a season away from a Mitch Marner potential extension as well as John Tavares current contract expiring so I'd venture to guess that this group stays together while next season becomes the one where things may really shakeup from a roster standpoint.

*For continued fantasy news and notes, follow me on Twitter @ndySanz. Data from CapFriendly