Let’s start this off with the obvious warning: with the top half of the hourglass as empty as it is, a lot can change in a hurry. This post might become antiquated from the time it takes to hit publish to the time I post a link on my personal Twitter account.

Yes, we’re that close to the deadline on William Nylander’s season. If Nylander has not agreed to terms on a contract at 5:00 PM Eastern Time on Saturday night, he won’t be playing in the National Hockey League this season. He’ll become the first RFA of note to do so in the Salary Cap era if it comes to that. The first arrival of the “Big Three” kids, sitting at home in Sweden as the Leafs make their most realistic bid for the Stanley Cup in generations; for much of their fanbase and all of the roster, in their lifetimes.

How did we get here?

No One Is Guilty, No One Is Guiltless

Trying to make sense of what’s gone on over the past few months is very difficult. Really, even the insiders are stitching together each other’s micro-reports, trying to figure out pieces of the story. The Leafs aren’t talking, nor are Nylander’s camp (himself, his family, his agency, etc).

What we think we have so far, based on everything we know, sounds something like this: The Maple Leafs are trying to get Nylander to sign a team-friendly deal, and entered the negotiations at around $6 million, with Nikolaj Ehlers as a comparable. Nylander’s side went with a different player from the same 2014 draft class, identifying Leon Draisaitl’s $8.5 million per year as a little more than they’re looking for, but that $8 million would be fine.

A big reason why Nylander supposedly (again, we’re working on stitched reports) made his big ask? Concerns about his future. Specifically, that he’d be the odd man out eventually, and that he wanted a deal that would make other teams second guess, and if they committed to pulling him away from Toronto, he’d at least be getting paid. Both sides want a long-term deal; neither wants to be back at this table again in a few years, and both hope that once it’s signed, that business can carry on as usual.

These are normal facets of negotiation, but what’s not normal is that, from what we’ve observed, nothing really changed on either side for months, even as the season began, even as Dubas and Nylander met in Switzerland, and even as November began.

It’s difficult to truly blame either side, because you can see where they’re both coming from.

For the Maple Leafs, they’ve got a ton of high-quality players coming up on their first truly negotiable contracts in the next year or so, and a few of their iffier deals stand as roadblocks as well. The salary cap truly accelerates the death by a thousand paper cuts, and there are already a few gashes on the books. They need to shave dollars on pretty much every renewal, so a good first impression is especially key.

For Nylander, you look at what other young to prime age, already established stars are getting on their recent deals, and you wonder if $6 million is enough. You hear people say “well, you aren’t David Pastrnak!” and “well, you’re not Johnny Gaudreau!” and you can’t help but point out that those two have proven to be high-value contracts; especially considering there is personal stake in it for Nylander (one of Pastrnak’s best friends) and agent Lewis Gross (who represents Gaudreau and would likely want to end up with a better result here).

But it took until this week for Nylander to come down, and for the Leafs to come up. Nearly half a year of not budging. As much as you respect both sides, that’s an awfully long time to play a game of chicken, especially while a quarter of the season burns out. From both perspectives, I can see why there would be a sense a frustration.

It should be a two-way frustration though, and it shouldn’t be one of outright anger. “It’s the way the business works” is a term we usually use for the tough decisions that come in this game, and it applies here – both sides are completely right and had they not been up against each other, would probably cheer on each other; the Leafs camp cheering on each other’s motives.

It’s a shame it got here, but it’s best to look at this as a good-intentioned battle of stubbornness, an unstoppable force versus an immovable object, rather than a negotiation with a hero and a villain. No matter what happens, it’s been made pretty evident that both sides have sat here with a goal of William Nylander being a Maple Leaf for a very long time; a trade, a trade request, or a bridge deal would have happened sooner if that wasn’t the case.

Should He Return…

There has been concern about what the reaction will be to Nylander’s return in the probable event of it happening. That comes from a few directions – how does the team react to him as a person? How do the fans embrace him? How does the front office react with its transactions?

To the first question, I figure that the Leafs would welcome Nylander back with open arms. Now, this could have been different had they been struggling; to hold out for a bigger paystub while your teammates are slipping down the standings could be seen as a disloyal move. But, Toronto is second overall without much sign of slowing down; his return is closer to a stimulus than a bailout, and as such, they’ll likely see it as more of a part of the process, and a guy sticking up for their own rights as players as well.

The fanbase will be a different story. Not everyone will feel the same as I rationalized in the above segment; many see this process as a sign of disloyalty on Nylander’s end, and many are willing to brush off the concept of scale and feeling valued by pointing out that the annual salary being offered is enough for most people’s lifetimes (which, while it misses the point of who makes the money and how much richer the owners are, is a somewhat understandable rationale). It might take some time for people to come to terms with how long it’s taken Willie to, well, come to terms.

All the same, a lot gets forgiven once the player is on the ice, especially if they come back with open arms. Everything we know about the process suggests that if Nylander dons the blue and white in a game situation again, it’ll be with excitement and relief – not frustration. It’ll also be with the talent and upside he’s shown for years since Toronto drafted him. As this process has gone on, people have begun to doubt how much he contributes, but the reality is that 60-point young wingers who can also play centre are rare, that he’s put up points at obscene, historical rates in every league he’s played in, and that he’s proven himself to pick up Auston Matthews at 5-on-5 as much as Matthews picks him up; 34’s shot and two-way play will always make him a franchise forward, and he’ll find success with most skilled wingers, but it’s the addition of 29 to his flank that really creates a top-end cycle game.

Once we see a few of those keep-away sequences, saucer passes, and swooping wrist shots, the crowd will be back.

As for the lineup, I’m pretty curious to see where that goes. Most are expecting one of Martin Marincin or Justin Holl to be placed on waivers. I’m not so sure of that; both of those are players that Kyle Dubas has valued over the years and would likely want to find space for, Mike Babcock agrees with him on at least Marincin, and has vouched for the usefulness of carrying eight defencemen. Tyler Ennis or Josh Leivo could be moved, but both have been producing of late. Frederik Gauthier being placed on waivers would have been a gimmie had this happened in October, but his strong play in a traditional fourth line role might make that risky. My guess is that Gauthier is shopped around the league to see if anyone would move a low pick or waiver exempt/cleared forward for him, and if not, they’ll take the chance. Losing Gauthier as he finally shows NHL ability would be a shame, but with his production still not keeping up to the other facets of his game, he’s probably not long for an organization that’s got a surrounding pipeline of skilled forwards knocking on the door either way.

The Could And They Should

Another elephant in the room, more so in both broadcast and social media, is whether or not keeping Nylander is even the correct decision. That, as good as he might be, maybe he’s not needed, and that he should be used to address a need. Specifically, most bring up getting a defenceman in return, because Toronto needs one of those and if they have him signed, they won’t have cap space to get one.

To me, that doesn’t make a ton of sense. The first reason focuses strictly on what you get back; how much does moving him for the best defenceman put up for sale really help your team?

While you might not end up making a trade with the gravity of Taylor Hall for Adam Larsson, the player that comes back the other way has to be given up by the other team. There hasn’t been a lot of talk about defencemen being shopped this year, and the ones that do come up range from the bottom barrel of the league (Erik Gudbranson), to the cap misfortunes (Kevin Shattenkirk) to “guy that analytics people thought were undervalued years ago, so that must mean Dubas would trade a star forward for him now” (Jake Muzzin, Chris Tanev, any Carolina Hurricanes defenceman not named Dougie Hamilton, etc).

Secondly, there isn’t anything that inherently suggests that Toronto needs to get better defensively to win – the name of the game is goal differential and games that are forced to be high-pace are usually more likely to be won by the team with more talent (more coin flips, greater chance of regression to expectation). Not to mention, Toronto’s goaltenders both appear to be en route to capable enough seasons, Toronto’s current dressed defensive corps likely isn’t even optimally deployed yet, and Nylander should add some defensive value on both sides of the ice by upgrading the forward depth.

Lastly, the push for a defenceman is a band-aid solution. Toronto has two of the best young defensive prospects in the American Hockey League right now in Timothy Liljegren and Rasmus Sandin, who both seem to be on trajectories to become NHLers within a year or so. Several others sit on the bubble, and the Leafs invested heavily into other transition-type defencemen at the 2018 draft. Even the main roster should have answered some doubts; Morgan Rielly and Travis Dermott’s step forward essentially filled the archetypes that people were searching for in a trade when all these suggestions started over a year ago.

That Toronto will have to move Nylander or any other top forward (Marner, Matthews, Tavares) solely because of the salary cap crunch is also a sign of poor understanding of roster composition.

Yes, there will be tightness towards the top for the first few seasons, as carrying four star-to-superstar forwards on proper contracts is pricy and the cap can only go up so much until the Leafs print enough Stanley Cup Champions hats to boost Hockey-Related Revenue singlehandedly. But when looking long-term, the priority should be to keep your core players together and swap out the parts they drive, not sell off the core to make room for the parts.

After all, the Chicago Blackhawks won all of their cups with Jonathan Toews, Patrick Kane, Marian Hossa, Duncan Keith, and Brent Seabrook. The Pittsburgh Penguins won all of theirs with Sidney Crosby, Evgeni Malkin, Kris Letang, and Marc-Andre Fleury (not to mention, won two of them after a six-year drought by adding Phil Kessel). The Los Angeles Kings both of theirs with Anze Kopitar, Drew Doughty, Jonathan Quick, Jeff Carter, and Mike Richards.

What made those teams competitive, even with a few of those big names eventually getting less-than-good contracts handed to them, was that they swapped out the fringes continuously, selling the accessories at a premium after big years and deep runs. Toronto should know this all too well, messing up the Chicago tax twice with Kris Versteeg and Dave Bolland. The Leafs’ success will come in how they parlay the Kapanen’s, Hyman’s and Johnsson’s of the world for assets to find the next ones, how they find ways to move and not re-enact the Marleau’s and the Zaitsev’s, so on and so forth. Nylander returns to this Leafs lineup as somewhere between the third and fifth best Toronto forward, but that doesn’t change the fact that he’d be future piece A or B on a very large quantity of NHL teams.

The same goes for Marner if the price doesn’t get into the amounts that major media seems to like to speculate (he’s great, but not 10-12M great), and Matthews at just about any price (though one hopes for, well, that 10-12M range), and the same goes for Tavares for at least a little while (eventually, he might end up getting Brian Campbelled). Hockey becomes a strong link sport come playoff time, so giving up one before you have to seems unnecessary – especially when you’ve got an elite scouting and development program to run your secondary talent conveyor belt.

But Will They?

The clock is ticking. As I type this sentence, I see 22 hours remaining, and I don’t see a Swedish Phenom in his proper uniform (though, to his credit – lots of training t-shirts and practice gear has remained on him since the summer – again, this is a kid with the Leafs on his mind).

It’s going to be tense, but I think it gets done. The Leafs won’t make a panic trade, and while I’m sure they’d like it if Nylander came all the way down on his ask tonight, they’ve proven enough of a point over the past few months about not caving that they can make another slight concession to get this over the hump. It helps that Nylander is a player that means a fair bit to those at the helm; his selection was the effective start of the Shanaplan, and he was Patient Zero for the high end of Kyle Dubas’ Marlies development program. He was the first piece of the big three that Mike Babcock got to coach. They can talk about doing what’s best for the bottom line all they want, but as long as it’s reasonable, it’s going to be hard for them to detach from him.

Nylander knows he won’t be making more money by sitting out the year, he knows a good shot at a ring is at stake, he’s a player who enjoys the game, and he’s got Toronto into more reasonable territory for him over the past week.

Whether it’s tonight or early tomorrow, I see a deal happening. Long term, and fair. My guess along this process has been six years at $6.75 million per, and while those numbers may shift a bit, I’m going to hold firm on it.

Then again..

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