In the summer of 2010, San Jose Sharks General Manager Doug Wilson signed then-Chicago Blackhawks defenseman Niklas Hjalmarsson to a four-year, $14 million offer sheet. The offer sheet came just six weeks after Chicago swept San Jose in the Western Conference Finals, and was a win-win for Wilson. If Chicago matched, they’d have less salary cap space to retain pieces from their Cup-winning squad, and they’d lose a young, top-four defenseman if they didn’t.

Seven years later, Wilson has a chance to do something similar to another rival that eliminated the Sharks in the postseason. The Edmonton Oilers did not win the Stanley Cup, nor do they face exactly the same salary cap crunch as the Blackhawks. But, they will have some tough decisions to make in the very near future.

Edmonton is set to sign center Connor McDavid to an eight-year contract extension worth $13.25 million annually, according to Sportsnet’s Elliotte Friedman. The deal would come into effect during the 2018-19 season, after McDavid plays out the final season of his rookie contract. Assuming the salary cap remains flat in 2018, Edmonton will have $20,224,666 in cap space to sign six or seven forwards, two or three defensemen, and a goaltender to get to a 23-man roster. Some of that space will be filled by players on their first contracts, such as Jesse Puljujarvi.

A lot of it will be needed to sign pending restricted free agent Leon Draisaitl to an extension. The Oilers have said they will match any offer sheet for Draisaitl, but a large contract could test their resolve and make it difficult for Oilers General Manager Peter Chiarelli to fill out the rest of his roster.

How does San Jose fit in? They have the salary cap space to sign Draisaitl to a massive offer sheet under the same reasoning they used to sign Hjalmarsson in 2010: improving the roster if it’s not matched, and hurting their rival if it is.

For starters, Leon Draisaitl is a very good player that would fit the Sharks’ needs. The 21-year-old center scored 77 points last year in his third NHL season. He has spent time on Connor McDavid’s wing as well, and has been a positive possession player relative to his teammates in each of his three seasons. Draisaitl would be the third-youngest player on San Jose’s roster, and fit into a young core of Sharks centers alongside Logan Couture, Tomas Hertl, and Chris Tierney.

Any offer sheet would cost the Sharks significantly if unmatched. Given how the NHL’s offer sheet compensation works, San Jose would have to pay a significant price financially, and in upcoming drafts, as the table below demonstrates.

Offer Sheet Compensation AAV Compensation AAV Compensation Less than $1,295,571 None $1,295,571-$1,962,968 Third round pick $1,962,968-$3,925,975 Second round pick $3,925,975-$5,888,960 First and third round picks $5,888,960-$7,851,948 First, second, and third round picks $7,851,948-$9,814,935 Two firsts, a second, and third round picks More than $9,814,935 Four first round picks

San Jose does not have a second or third round pick in next year’s draft, which limits their ability to make anything but the least and most-expensive offer sheets. The former isn’t a possibility, so that leaves the Sharks signing Draisaitl to an offer sheet worth more than $9,814,935 annually.

Let’s assume San Jose signs Draisaitl to a seven-year deal, the maximum allowed, worth the minimum amount in that range, $9,814,936. In terms of salary cap hit, that would make Draisaitl the fourth-highest paid player in the league right now, and the fifth once McDavid’s rumored extension comes into effect. That would leave San Jose with $6,717,897 in salary cap space for this season, including Kevin Labanc and Timo Meier’s rookie deals. Chris Tierney and Marcus Sorensen remain unsigned, and it all but rules out the Sharks retaining Patrick Marleau and/or Joe Thornton.

Assuming the salary cap stays flat, San Jose would have $23,753,397 in cap space for 2018, before contract extensions for Marc-Edouard Vlasic, Martin Jones, and Tomas Hertl kick in. Labanc and Meier would need new deals the following season, and without a first round pick from 2018-2021, replacing older players with young prospects on cheap contracts becomes harder.

So, the Sharks would have to overpay to sign Draisaitl. But as difficult as it would be for San Jose, it would be far worse for Edmonton. If Edmonton does not match, they’ll be able to recoup some of the value with four additional first round picks, but will lose a proven player for additional opportunities to replace him, not guarantees. If they do match, though, they’ll face significant challenges building a contending roster.

Assuming Draisaitl signs the previously speculated offer sheet and the salary cap remains flat, Edmonton would have just $10,409,730 in cap space when McDavid’s rumored extension kicks in. They’d need to sign one less forward, but would be unable to fill the holes on their roster without moving a big contract. The Oilers would probably prefer to trade Milan Lucic or Kris Russell, but may be forced to move someone like Ryan Nugent-Hopkins. It could also make it harder for Edmonton to re-sign 2018 restricted free agent Matthew Benning, forcing Edmonton’s hand much like Chicago’s was when they walked away from Antti Niemi’s arbitration award in 2010.

A Draisaitl offer sheet is a higher-stakes gamble than the one Wilson made with Hjalmarsson’s seven years ago. San Jose would stand to lose more picks, and be unable to re-sign more players if the offer sheet wasn’t matched. Draisaitl’s upside is higher than Hjalmarsson’s, though, and a matched offer sheet would impede Edmonton’s ability to build a team capable of running away with the division in McDavid’s prime. Either way, San Jose benefits, which makes a Draisaitl offer sheet worth serious consideration.