Maple Leafs and Nylander: Contract deadline, trade talk, more

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Despite Saturday’s 5 p.m. ET contract deadline being achingly close, it’s still any outsider’s guess what will happen between the Toronto Maple Leafs and William Nylander. For all we know, both the player and team aren’t 100-percent sure, either.

It’s also unclear how the Maple Leafs’ pending salary cap crunch will impact Nylander’s future with the team beyond 2018-19.

Let’s try to wade through the many ins and outs of this situation, with the best information currently available. If your head starts spinning, at least realize that you’re not alone.

Various rumblings about what a contract might look like with Toronto

During an NBCSN appearance on Wednesday, Bob McKenzie provided one of many possible windows for a Nylander contract. As opposed to many other situations where it’s difficult to hash out a deal, McKenzie reports that Nylander would actually not prefer a shorter “bridge” contract. Instead, he’d lean toward six years. McKenzie placed Toronto’s preferred cost at $6.7 million per year, while Nylander might want something closer to $7M.

This jives with figures from Sportsnet’s Chris Johnston, who somewhat recently placed a possible compromise at $6.9M per year.

(Such reports bring to mind a somewhat amusing cacophony. On one hand, it feels absurd that a few hundred thousand would make such a difference when you’re talking about multiple millions. On the other hand … most of us would absorb multiple slashes to our softest parts for that difference alone.)

Do note that McKenzie at least floated the possibility of what would be closer to a “bridge” deal, even if it doesn’t sound like this would be Nylander’s first choice:

One factor to keep in mind is that, if the Maple Leafs reach a deal with Nylander before that Saturday dinner deadline, it would be “prorated” since we’re already more than a quarter through the 2018-19 season. Cap Friendly broke down how such variables might play out:

Basically, either a three-year or six-year deal (or other permutations) could be a great fit for the Maple Leafs. The 2018-19 year of a contract would feature a significantly increased cap hit (which works for Toronto, as they’re flush this season before the crunch hits) and then years two and on would be deflated.

What if there’s no deal at all?

Nylander wouldn’t be able to play in the NHL in 2018-19, thus possibly forcing him to play in an overseas league (or, if he doesn’t want to risk injury, not play at all). In that McKenzie video, you’ll note that Nylander wouldn’t gain any additional leverage if he sat out a season, as he’s not yet eligible for salary arbitration.

A couple weeks ago, Pierre LeBrun brought up a different – though difficult to imagine, even now – Feb. 25 deadline in an article for The Athletic (sub required).

In that scenario, the Leafs would trade Nylander’s rights. Such a maneuver would essentially only open up possibilities for teams not making the playoffs, as Nylander would still be unable to play in the NHL in 2018-19.

Seems unlikely, right? It’s worth mentioning, especially as we move to more plausible trade scenarios.

Talking trades

That Feb. 25 deadline is part of a potential trade deadline. Let’s start with the earliest link in that chain: moving Nylander’s rights before Saturday’s 5 p.m. deadline.

Multiple reporters (including LeBrun) indicate that the Maple Leafs would prefer to sign Nylander, not trade him. Even so, Toronto GM Kyle Dubas is at least touching bases. TSN’s Frank Seravalli points to a specific team that’s been in contact: the Philadelphia Flyers.

Landing a prime winger like Nylander would certainly make a boatload of sense for the Flyers, particularly if they wanted to make a statement after firing a shocked Ron Hextall from his GM position.

Theoretically, another team would be able to add Nylander with fewer worries about the future. On the other hand, few teams really have the cap space to easily add Nylander’s prorated deal in, as discussed earlier in this post. During the latest edition of TSN’s Insider Trading, McKenzie notes that the trade market has been “shrinking” because of those cap concerns.

So, that would make Nylander tougher to trade … for this season.

What if the Maple Leafs sign Nylander, only to trade him in the future, even if he gets a longer-term deal? Sportsnet’s Elliotte Friedman grimly stated on “Tim & Sid” that he believes that Nylander won’t be a Maple Leaf after this season, and pegged the 2019 NHL Draft as possibly the latest he’d be traded:

One can debate the likelihood of any trade happening, but there are a few potential windows to consider. A quick “tl;dr” recap, then:

Potential path 1: Before Saturday’s signing deadline.
Potential path 2:Feb. 25 – no signing happens, but a team could trade for his rights for 2019-20 and beyond.
Potential path 3: Nylander signs a contract with Toronto, only to be traded by the 2019 NHL Draft?
Potential path 4: No trade at all?

The elephants in the room

Most likely know this full well, but 2019-20 and beyond looms as a conundrum for the Maple Leafs with good reasons: Auston Matthews and Mitch Marner need new contracts.

That Insider Trading segment noted that many big-ticket RFAs are preferring to wait until 2018-19 ends to really negotiate, rather than signing extensions now.

In the case of Marner, a proactive extension might not be especially cheap. Even at a shorter four-ish year commitment, a $10M number is being thrown around. Considering how many points Marner could put up during a full season as John Tavares‘ wingman, it’s no surprise that he could be pricey.

Matthews stands as almost certainly an even more expensive proposition. Could Toronto convince him to match Tavares’ $11M, or somewhere close? Would Connor McDavid‘s slight discount $12.5M serve as a ceiling? How will potential deals for other stars like Patrik Laine affect Matthews’ bargaining?

All of those questions – not to mention what to do with Jake Gardiner, and which steps to take to make the team better – don’t just plague the Maple Leafs for the future. They must consider them now.

Such a cap crunch might force Toronto’s hand with Nylander, even if they truly believe he’s worth paying in the $7M range. That’s especially true if, say, they can’t unload Nikita Zaitsev‘s deal off ($4.5M through 2023-24[!]) to a lower-end team at a price, or do something similar with the last year of Patrick Marleau‘s $6.25M cap hit.

Happy place

Of course, there’s also a possibility that the Maple Leafs have no intention to trade Nylander at all.

Let’s not forget that other teams have handled cap crunches to the point that they’ve at least retained their key guys. The Lightning defied odds in signing Steven Stamkos, Nikita Kucherov, and Victor Hedman; in many cases, Tampa Bay landed them below-market-value, sometimes by leveraging RFA years. While it’s true that the Blackhawks couldn’t walk the tightrope forever, they won three Stanley Cups in part because they were able to walk that thin line for a long time. Some of us thought they’d collapse much sooner.

Is it that outrageous to imagine the Maple Leafs making this work?

Granted, the recent history of tough contract holdouts and strained situations have often resulted in eventual trades. P.K. Subban feels like the most prescient example, yet there are others.

The Maple Leafs are run by what seems to be smart people, and Mike Babcock recently stated that he expects Nylander to be a “career Leaf.”

It’s not that difficult to imagine the Maple Leafs bribing someone to take a nonessential contract in exchange for assets or other considerations. They did it with David Clarkson‘s ghastly deal, and it’s perfectly plausible that they can make it happen again.

Let’s not forget that the salary cap has been rising, too. Last season, the ceiling was $75M, while it’s up to $79.5M for 2018-19. A comparable jump for 2019-10 might just give the Maple Leafs enough breathing room to afford Nylander, Matthews, Marner, Tavares, Frederik Andersen, and maybe even a few other players above a replacement level.

***

Complicated stuff, right?

The bottom line is that it’s very difficult to predict how this will play out, especially when you zoom out beyond the already-tricky deadline Nylander and the Maple Leafs face on Saturday at 5 p.m. ET.

For fans of the sport and/or those interested in team-building, it should be almost as fascinating to watch as it is to watch this blazingly talented Maple Leafs team actually play games.

What would you do if you were running the Maple Leafs? What do you expect to find out? We won’t have to wait long for actual answers.

At least, for some answers.

MORE: Your 2018-19 NHL on NBC TV schedule

James O’Brien is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @cyclelikesedins.