Nylander has only one year left on his contract. Let's explore the three directions the Leafs can turn.
theathletic.com
1. Extend him
Nylander’s last contract famously took forever to get done.
His agent, Lewis Gross, won’t be pushed around. Treliving knows this as well as anyone. Gross represented Johnny Gaudreau when Treliving, then the Flames’ GM, tried and failed to sign the star winger last summer.
Two questions to start us off here:
1. Do the Leafs and their new GM still want to be in the Nylander business?
2. If they do, how much are they prepared to pay?
We won’t really know how Treliving feels about Nylander until we see some action — i.e. a new contract or trade. But let’s say, for argument’s sake, that the Leafs want to keep Nylander around. What might his next contract look like?
Maybe the most pertinent comparable is the eight-year deal that Filip Forsberg signed with Nashville last July. Forsberg’s $8.5 million cap hit represented 10.3 percent of the cap at the time. Why Forsberg? He’s a similar-ish offensive player who had produced 0.83 points per game when he signed that contract.
Nylander’s career points per game to this point: 0.83.
Forsberg signed his deal as a pending UFA entering his age-27 season. Nylander, as we noted, still has a year left on the six-year deal he signed on Dec. 1, 2018. He’ll be 28 when his next deal begins at a time, crucially, when the cap is expected to rise a fair bit, perhaps in the range of $87 million or $88 million.
For our purposes, let’s split the difference at $87.5 million. A Forsberg-like deal, for eight years, would amount to just over $9 million on the cap annually. Now maybe Gross pushes for a slightly bigger chunk of the pie. Jeff Skinner nabbed 11.3 percent of the cap in 2019 ($9 million cap hit) over an eight-year deal. Jakub Voracek got 11.6 percent on his eight-year deal in 2015 ($8.25 million cap hit).
Twelve percent of that rising cap would equal $10.5 million annually, which would be one of the biggest cap hits in the entire league. That’s a bit rich. Hart Trophy finalist Matthew Tkachuk, younger and better than Nylander, got a $9.5 million ticket on the eight-year deal he signed with Florida last summer. That was 11.5 percent of the cap.
A seven or eight-year deal, with a $9-million-ish annual ticket, feels about right and would place Nylander — for now, anyway — just inside the top 25 NHL forwards.
Right where he belongs.
Last season, Nylander ranked 19th among his peers with 87 points and tied for 14th with 40 goals.
.................
A related and very significant part of this conversation is whether the Leafs believe that Nylander will perform better than he has to this point in the postseason. He’s absolutely made strides and performed better, for the most part, than his co-stars, Auston Matthews, Mitch Marner and John Tavares.
Part of me wonders whether he’s been dragged down a bit by Tavares. Their connection has been a problem for the Leafs in both the regular season and playoffs.
..................
Nylander would remain a trade asset even if the Leafs were to extend his contract, assuming, of course, that they can limit the no-trade protections. And that has to be factored in, too. Extending Nylander would more than likely cement the same core for at least another season, after which Marner will be due an extension. That is, unless they opted to deal Marner before then. Do they want to run it all back?
One curiosity: If they can’t come to an agreement before the season, will Nylander insist on halting negotiations? And if so, will the Leafs be tempted to choose Path No. 2?
2. Trade him
Part of the trouble with waiting that long is the no-trade clause that will kick into Nylander’s contract on July 1.
It’s only 10 teams, but 10 teams is still 10 teams.
Part of the challenge with any Nylander trade is that a) That team will have to be one that’s presumably motivated to sign Nylander (otherwise why pay good assets for him in a trade?) and b) Nylander will have to be motivated to sign with that team.
So if the Leafs decide they don’t want to pay Nylander, or don’t think they can come to an agreement, the best time to trade for Nylander is now.
Is trading Nylander a good idea? It would obviously depend on the return. And that’s in part what scared them off from dealing Nylander in the past: The Leafs just didn’t believe that trading Nylander would make them better.
What might they want back in some kind of sign-and-trade or, less likely, a swap that doesn’t include a new contract for Nylander right away?
Ideally, a No. 2 centre, as detailed here.
If not, the Leafs might look to acquire a different type of winger for Nylander, maybe one who brings more size and physical oomph to the table. Someone like Pavel Buchnevich maybe, the 6-foot-3 Blues winger who has two years left on his deal at $5.8 million on the cap. Does St. Louis, who was reportedly interested in Nylander in the past, see a swap like that as an upgrade if they can lock up Nylander for the long haul?
Or could the Leafs maybe take a swing on a young guy who hasn’t quite popped yet, such as former No. 1 overall pick (and pending RFA) Alex Lafrieniere, plus other goodies?
The Rangers are always hunting stars and are about to lose Patrick Kane and Vladimir Tarasenko to unrestricted free agency. The Panthers also tend to go big-game hunting, and you’d think a team like the Hurricanes would greatly value a player like Nylander.
Treliving could also look at Nylander as the means to improving the defence.
Could they somehow do both, address forward and defence, as Treliving did when he swapped Tkachuk (younger and better than Nylander) for Jonathan Huberdeau and MacKenzie Weegar, plus other stuff, last summer? He also did the same sort of thing when he dealt Dougie Hamilton way back when.
Elias Lindholm and Noah Hanifin both have one year left on their deals in Calgary. If the Flames can’t extend Lindholm for whatever reason, is there some sort of swap there that makes sense if Nylander signs an extension? Would the Leafs want to pay Hanifin and Lindholm, who would improve things at centre (perfectly) and on D (less perfectly)? Would the Flames want more in that case? Would they look to include Timothy Liljegren and, if they did, would the Leafs insist on more in return? Are the Flames even willing to move Lindholm?
Trading Nylander for a collection of blah assets is obviously one worst-case scenario. The other is trading Nylander for a blah player, a la Taylor Hall–Adam Larsson.
You don’t often see contending teams trade players like Nylander, and for good reason: It’s hard to do it right — to make your team better or different even, just not worse.
3. Do nothing
All of this is what leads teams — again, good teams! — to simply hold onto useful players on expiring deals.
We’ve seen the Leafs do this repeatedly. James van Riemsdyk. Tyler Bozak. Jake Gardiner. Frederik Andersen. Zach Hyman. Ilya Mikheyev. Jack Campbell.
None of those players were quite on Nylander’s level (though Hyman has continued his forever upward ascent in Edmonton). Having a star like Nylander simply walk away in free agency next summer would sting more than any of those dudes did in summers past.
That’s the clear Gaudreau-like downside here.
The upside: The Leafs would get one more season of Nylander at a discounted rate of $6.9 million on the cap. It’s not impossible, either, that Nylander would re-sign next summer. Avalanche captain Gabriel Landeskog went to the eve of free agency before he finally re-upped in Colorado. Steven Stamkos memorably did the same in Tampa following a famed meeting with the Leafs.
In addition to Nylander, the crop of potential free agents in 2024 could include Stamkos, Sebastian Aho, Anze Kopitar, Chandler Stephenson, Mark Scheifele, Teuvo Teravainen, Connor Hellebuyck, Lindholm and Devon Toews. (There’s also that Matthews guy, who will presumably be locked up by then.)
All of which is to say that Nylander would rank among the most coveted players available. That could mean an even bigger payday than the one he might be looking at now.
Does letting things play out with Nylander mean the Leafs are prepared to let him walk? Not necessarily. The Flames tried until the very end with Gaudreau. And the Leafs could conceivably do the same with Nylander.
It’s possible they struggle to sign him now for whatever reason, fail to come up with a suitable trade, and simply decide to hold onto him for one last year instead. It doesn’t feel like the optimal asset management, but neither does the alternative of making a subpar trade just because you’re fearful of losing him for nothing (though again, it’s not really nothing because you’re getting him for one more season). Were Nylander to simply walk away next summer, the Leafs would be left with Matthews, Marner (presumably) and a soon-to-be 34-year-old Tavares, entering the last year of his contract.
Which makes doing nothing the least attractive option.
A trade — the right trade — makes sense. So does signing Nylander as his trajectory is still pointing upward. He’s also long-term star power for the Leafs as one long-time star, Tavares, ages.
The Leafs and their new GM have an interesting decision to make.
www.thestar.com
