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Could the Sharks trade for William Nylander?

With the Maple Leafs coming to town tonight, and at the bequest of Sharks captain Joe Pavelski, we thought we’d discuss what the Sharks can, should and will offer for William Nylander.

This one’s for you, Pavs.

According to Elliotte Friedman, Leafs millennial GM Kyle Dubas is running out of patience in his negotiations to strike a deal with the disgruntled 22-year old Leafs forward and has asked teams to notify him of what they would be willing — and not willing — to offer for the rights of the disgruntled restricted free agent.

Nylander is said to be asking for a long-term deal worth $8 million per year, the range of which players such as Phil Kessel, Ryan Johansen, John Carlsson and our own resident Wookiee, Mr. Brent Burns sit. Meanwhile, Toronto is said to be set on a maximum offer of a long-term deal worth $7 million, hence the deadlock.

With that said, how can, should, and will Sharks GM Doug Wilson approach this situation?

On the one hand, throughout his tenure as Sharks GM,Wilson has consistently touted the notion of “always looking to improve” both in rhetoric and, for the most part, in action, as evidenced with San Jose’s consistency in acquiring trade deadline pieces and elite-caliber players such as Joe Thornton, Dan Boyle, Dany Heatley, Brent Burns and most recently, Erik Karlsson. But on the other hand, Wilson’s hands are seemingly tied, given the Sharks’ current cap situation. With only roughly $1.4 million in cap space as it stands, either some pieces or a large piece would need to be moved if the Sharks were to be able to fit in a future contract such as Nylander’s which presumably will fall between the $7-8 million range (for these purposes, we’ll assume that figure to settle at the midpoint, $7.5 million).

What can the Sharks offer?

Well, technically Wilson can offer Paul Martin’s now-retired jock strap and a bag of pucks, but there is obviously a need to consider what the Leafs are looking for in return for such a deal. Firstly, one would assume that Dubas would have a preference to ship Nylander out of the conference to a team in the West. That is usually a goal for General Managers when they face an imminent trade of a high-caliber player, (think Subban for Weber, Hall for Larsson, Karlsson to San Jose, etc.), but it is not entirely certain just how much of an actual emphasis is placed on that goal. It is definitely not the be-all end-all, but something worth considering as a possible tiebreaker edge for the Sharks should an Eastern team, such as the Carolina Hurricanes who are rumored to be very much in the Willy-sweepstakes, offer a deal of close-to-equal desirability for Dubas.

Secondly, and far more importantly, Dubas will look to acquire a piece or pieces that will help for areas of need. With the Leafs as one of the top teams in the league this season, holes on the roster are far and few in between. Defenseman Morgan Reilly’s exceptional start to the season has him leading the team and all NHL defensemen in points so far at the quarter-mark of the season. However, the team is rumored to be in search of a right-hand defenseman to pair with him as they, like the Sharks, look to be going all-in for a Stanley Cup push this season.

The Sharks happen to have an embarrassing riches of those.

San Jose currently has Karlsson, Burns, and Justin Braun on the right side of their three pairings. Any one of these three defensemen arguably plays on the top pairing on many other teams. It seems highly unlikely for the Sharks to involve Karlsson in a deal to an Eastern Conference team, even if he decides to let Wilson know tomorrow that he intends to walk away in free agency at season’s end, God forbid, given that such a deal would involve the loss of further assets for the Sharks based on the conditions of the Karlsson deal from Ottawa. This leaves Burns and Braun as the likely players that Wilson can offer the Leafs for them to realistically consider, with Burns presumably a one-for-one offer for Nylander and Braun as the likely centerpiece along with Kevin Labanc (a prospective top-6 forward like Nylander with less ceiling potential) and Melker Karlsson (Sharks need the cap space to make Willy work).

What should the Sharks offer?

Deliberately omitted from the above discussion was how the Wilson’s approach should be with regard to the Nylander sweepstakes, which we’ll discuss now.

Like the Leafs, the Sharks are also a top team in the league, albeit more-so in true capability than in the current standings. Acquiring a piece like Nylander and parting with either Braun and Labanc or just Burns could potentially backfire and disrupt team chemistry or create another even bigger deficiency on defense in the pursuit to improve another. But it could also push them over the top. Let’s review the impact of the two potential deals.

A Braun and Labanc package, along with Melker Karlsson and Radim Simek, obviously would have the prime benefit of netting Nylander and a surefire long-term top-6 forward, assuming he signs. It also likely forces a Vlasic/Karlsson reunion pairing. It gives the Leafs that stable stay-at-home partner for Reilly on the top pairing, while also netting a third-line winger in Labanc with upside to play on Kadri’s wing with second-line upside. The Melk-Man can kill penalties so there could be a spot for him at times on the fourth line, but a cap hit at $2 million with another year left on his deal makes his contract more liability than asset, particularly because the Leafs will look to have as much cap space as possible with the Auston Matthews, Mitch Marner and Kasperi Kapanen extensions looming this summer.

Should the Sharks do this deal? Probably not. It seems risky to part with Braun and Labanc, and it would just add one more big-time long-term contract; the Sharks would have to become the Warriors 2.0 in relying on their big-time players, but signing the rest of the team at the league minimum. Most importantly, adding another contract like that makes it close to impossible to re-sign Karlsson (let alone Pavelski), which, make no mistake, needs to be the team’s priority. Nonetheless, there’s certainly a case to be made that they should make that offer, given Nylander’s youth and upside.

How about the Leafs? They are even less likely to accept this deal, for as helpful as Braun would be on their roster, and Labanc too, it seems like a quantity for quality package that most GMs situated outside of Canada’s capital look to avoid. Let’s not forget that elite ordinarily begets elite in NHL deals, and the Thornton/Karlsson deals are not the norm. The Leafs gladly accept a Braun plus Timo Meier deal however, and may even throw in a first-round pick to make it happen, but the Sharks don’t accept that because of value and cap.

A Burns for Nylander swap though is far more interesting to consider for both teams.

As discussed, Toronto is in a prime position to win now. Adding Burns to their roster propels them to being the best team in the league. There is no question that in a pure value vacuum, this deal is one Toronto makes. There are two caveats that one would assume would drive Dubas to reject this deal at first glance.

First, from a purely cap perspective, Burns’ contract would make things more difficult, but still not impossible to re-sign the three core forwards this summer (“You’re not John Tavares yet, Auston Matthews! Get off your high horse and take a little less money!” — Dubas, probably). Second, there’s the fact that Burns is 33-years old while Nylander is 22. Conventional wisdom thus dictates that the former is a depreciating asset with less worth, while the latter is appreciating with higher value.

But here is why it may not necessarily be as simple as that.

Toronto is both a very young team with a bright long-term future ahead. What’s more is that Burns is the type of defenseman that has a unique combination of strength, size, skating ability and ability to get pucks to the net from the point as quickly as anyone else in the league. Sure, Wilson’s deal in signing him at an average annual value of $8 million over eight years is not going to look very good when the Wookiee turns 40. But it may not necessarily look as bad with him at 36 or 37 as one might ordinarily think. Once again, Toronto’s core consists of very young players, so even assuming that Burns’ play falls fast — again unlikely — an older Burns won’t be nearly as detrimental on a Leafs team with numerous players about to hit their prime than on other teams. Even with this assumption, the idea of current-Burns helping Toronto as a key player in making a number of serious Stanley Cup pushes over the next couple of years, likely winning one or two along the way, before reaching that point should make his latter depreciating years worth it for Dubas.

Meanwhile for San Jose, a relatively older Sharks team with less upside in five years time has projected trend reversed without jeopardizing current cup aspirations. The team gets younger, solidifies their top-6 both now and in the future, and just may make a move that keeps a certain Swede in town for the long-run too. Marcus Sorensen secretly fears the Wookiee and will be far more at ease and willing to resign with him gone, sure, but a Burns deal also allows Erik Karlsson to man the helm on the team’s blueline and may just be incentive enough for him to stick around if it means him being “the man.” This is conjecture, but nonetheless reasonable conjecture, unless Karlsson is the Kevin Durant type, who is looking to have help on the blueline in winning championships while having off nights from time to time and playing less minutes. But Karlsson doesn’t seem to be that type of player, instead getting stronger (and happier) with more playing time. Oh, and adding another Swede in Nylander isn’t something Karlsson would be entirely against, either.

What will the Sharks offer?

Based on evaluating Doug Wilson’s willingness to bring in big-fish over his tenure as Sharks GM, there should be consensus that he will at the very least explore every possibility with regard to the possibility of bringing in Nylander.

What that would entail however is less certain. Would Wilson ask Burns to list the three teams he would accept a trade to as per Burns’ right with his limited no-trade clause? Would the risk of not having Toronto listed as one of those teams be worth causing Burns to become upset with the organization and possibly disrupt his on-ice play? (Probably not, but something to consider.) The strategic calculus at play in this trade proposal is fascinating: both teams seek to win now and in the future, both teams will be tight-pressed against the cap by the summer, and both teams would receive a rare elite piece in exchange for an area of surplus — a surplus that is, you guessed it, rare to have in and of itself.

What do you think? How should Wilson approach the Willy-Willy Derby? Write your thoughts in the comments below.

This is CheechYou signing off.

And as always…

Keep Rosterbating.

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