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Mapping out the Sharks' route to a long-term extension for Erik Karlsson

The Sharks are introducing Erik Karlsson to the fans and media Wednesday, but it will be back to business soon with an extension for the blueliner at the top of the to-do list.

It begins Wednesday. For the first time in his nine-year NHL career, Erik Karlsson will be pulling on a uniform that isn’t that of the Ottawa Senators. Following the blockbuster deal that brought Karlsson, 27, to the San Jose Sharks last week, Karlsson will be stepping foot on the ice to practice as a member of the organization for the very first time.

The fanfare surrounding Karlsson’s first skate as a Shark won’t conclude when the practice session ends, however. Later in the day, the franchise plans to introduce the blueliner, who is arguably the biggest acquisition the franchise has made since acquiring Joe Thornton from the Boston Bruins nearly a dozen years back, at a press conference downtown. There, he’ll pull on the real threads — the teal game-day jersey, with his No. 65 stitched to the back — for the first time. It’ll be cause for celebration.

But as GM Doug Wilson sits nearby and watches his latest trade masterpiece get welcomed into the organization, and the city, with open arms, he’ll do so aware that the real work is only beginning.

In fact, as incomprehensible as it might sound, acquiring Karlsson could almost be considered the easy part. That’s not to say it didn’t require some hard work. It did, no doubt. But after Wilson was finally able to get the deal done with a package that included a pair of roster players, a pair of prospects and four picks with a boatload of conditions, he still has to take care of one of the most pressing pieces of business as it pertains to Karlsson: ensuring that the trade wasn’t done as a rental. That means over the coming weeks, possibly even months, Wilson will need to hammer away at a new contract for the two-time Norris Trophy defenseman in hopes that Karlsson’s stay in the Bay Area isn’t one-and-done.

Without any consideration of the salary cap, of course, we have an idea of what to expect out of a contract for Karlsson. Truth be told, we’ve known from the moment Drew Doughty signed his monster eight-year extension with the Los Angeles Kings. That pact, one Doughty inked with one year remaining on his current eight-year deal, has an $11-million average annual value. It comes with $20 million in signing bonuses in the first four seasons, including a whopping $10 million to be paid out on July 1, 2019. The deal also carries no-movement and no-trade clauses. And Doughty’s contract as the closest comparable becomes all the more relevant now that the two are playing in the same division, particularly in a climate where post-tax earnings has become an increasingly buzz-worthy topic.

The reality of the situation, however, is that no team is operating with a clean slate. No team is able to ignore the salary cap and what handing such a contract to Karlsson might do to their pay structure. And that’s certainly not the case in San Jose, where cap space was already beginning to get tight. That puts pressure on Wilson not only to sign Karlsson, but to map out the future with the blueliner locked in at what is sure to be an eight-figure cap hit.

So, what would that look like? Well, here’s what we know. At present, the Sharks are projected to have in the neighborhood of $25.7 million in cap space for next season, according to CapFriendly. If we conservatively estimate a modest rise in the spending limit — say, $1.5 million — the Sharks would then have just north of $27 million with which to work. More than one-third of that space, however, is going to be dedicated to Karlsson. In fact, if he matches his closest comparable, which is Doughty, Karlsson’s contract will chew up $11 million next season and leave the Sharks with somewhere in the $16-million range.

That isn’t quite as much financial flexibility as it would appear, though. Currently, the Sharks have 10 players locked in for next season, and Karlsson would be their 11th. But that would leave $16 million for Wilson and Co. to fill out another 11 spots on the roster. Already an unenviable task, doing so becomes that much harder when considering Joe Pavelski, Joe Thornton and Joonas Donskoi, three lineup regulars, aren’t among the 10 players already locked in.

Pavelski poses the biggest problem. The Sharks captain is second only to Brent Burns in scoring over the past three seasons, and his 89 goals and 212 points over the past three campaigns, not to mention whatever he adds to his totals this coming campaign, will all but ensure he’s due a raise on the $6 million he’s set to earn this season. And with the similarly aged Blake Wheeler, though slightly more productive, getting a five-year, $41.25-million extension earlier this summer, Pavelski’s future number would project to be at least in the $7-million range. If that’s what he’s after — and if it’s what he eventually what he receives from San Jose — we could estimate the available cap space could be chopped down to $9 million.

With that in mind, tough decisions may need to be made on Thornton and Donskoi. The latter, especially as a soon-to-be 27-year-old, is unlikely to want to take a pay cut to stay in San Jose, and the most likely scenario would see him bolt to the highest bidder. The former, however, might be willing to take a pay cut to stay in San Jose, if he stays around at all. Thornton will be 40 by the time the 2019-20 campaign rolls around, and it might be time for the surefire Hall of Famer to head for retirement.

That would leave $9 million for the Sharks to ink seven more forwards to ice a full four-line offense and round out the defense with one additional blueliner. Six projected roster forwards — Timo Meier, Kevin Labanc, Barclay Goodrow, Marcus Sorensen, Antti Suomela and Maxim Letunov — are set to become RFAs next season of varying degrees. (Goodrow is the only one with arbitration rights.) The Sharks are provided some semblance of cost control there. Likewise, defenseman Joakim Ryan will be an arbitration-eligible RFA. But with $9 million in estimated cap space, San Jose would have to average $1 million per player to fill out their roster if the cap sits in the $81-million range next summer. The possibility that Dylan Gambrell and Alexander True make the jump to the NHL could help the Sharks save against the cap, but it could also mean forcing their development along at a rate that’s not conducive to success at the next level.

So, at that point, one has to wonder if a cap casualty isn’t the answer to any cap problems that could arise for the Sharks on the heels of a potential Karlsson extension. And, whether San Jose fans will like it or not, it appears the two most likely candidates are those who Karlsson will be taking minutes from this coming campaign: Justin Braun and Brenden Dillon. At respective $3.8-million and $3.27-million cap hits this coming season and next, neither will open up considerable space that can be used on a big-ticket acquisition. What trading one or the other would do, though, is open the door for a fourth-line addition through free agency or a more cost-effective option up front or on the blueline. Any savings can be kicked back to re-sign the several RFAs who will be looking for new deals come season’s end.

No matter how the Sharks get there, though, it’s evident that a Karlsson extension has now vaulted to the top of the priority list. San Jose has assembled a team — especially a blueline — that is capable of achieving something special. Now it will be up to Wilson to make sure he gives this group more than one kick at the can.

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