February 15, 2023 by Eric Friesen

After the Detroit Red Wings captured back-to-back Stanley Cups in 1997 and 1998, then-General Manager Ken Holland looked to make a major addition at the trade deadline to boost their chances for a third consecutive championship. On March 23, 1999, the Red Wings acquired future Hockey Hall of Fame defenceman Chris Chelios from the rival Chicago Blackhawks in exchange for Anders Eriksson and two first-round picks in 1999 (Steve McCarthy) and 2001 (Adam Munro).

Despite being 37 years old at the time of the trade, Chelios went on to play for a decade in Detroit, and helped the Red Wings win two more Stanley Cups in 2002 and 2008. 24 years later, Holland is now running the Edmonton Oilers’ front office, and looking to bring in a similar impact player to help put his club over the top. And that player could be elite puck-moving defenceman Erik Karlsson.

TSN’s Chris Johnston tweeted on Saturday that the Oilers have re-engaged in trade discussions with the San Jose Sharks involving Karlsson. And while there are considerable financial hurdles on both ends, this is at least the second time this season the two clubs have explored a potential fit.

Johnston expanded on this tweet on his podcast: “The fact that they’ve have tried once, and are trying again, and it’s two or three weeks until the trade deadline, it’s pretty notable that’s where the Oilers’ minds are at,” he said on The Chris Johnston Show on Monday.

Karlsson’s resurgence

Between 2011-12 and 2018-19, Karlsson led all NHL defencemen in assists (381) and points (492) in 590 games. The two-time Norris Trophy winner recorded one 80-point season, four 70-point seasons and six 60-point seasons during that span.

But after signing an eight-year, $92 million contract extension with the Sharks on June 17, 2019, which made him the highest-paid defenceman in the league ($11.5 million cap hit), his production dropped off. This season, however, Karlsson finds himself back to his Norris Trophy form.

The 32-year-old has 73 points in 54 games this season, ranking him sixth in the NHL scoring race. His 55 assists are also tied with Connor McDavid for second in the league. He’s just six points away from setting a career-high in points, and is surely the frontrunner for the Norris Trophy.

More impressively, Karlsson is on pace to become the first defenceman to record 100 points in a single season since Brian Leetch in 1991-92. While he’s undoubtedly one of the best players of his era, few would have predicted Karlsson to have a career-year at age 32. And even fewer probably would seen it happening with the 28th place Sharks.

What would it cost the Oilers to bring him in?

As recently as this past off-season, Karlsson’s contract seemed untradable for the rebuilding Sharks. Now, Karlsson is being a viewed as a major target target for Stanley Cup contenders at the deadline.

Daily Faceoff’s Frank Seravalli reported on January 13 that the Sharks were seeking three first-round picks in return for Karlsson, while retaining 18 to 20 percent of his contract. It would be an enormous price to pay, but in order to get quality players the price will always be expensive. Still, you could make the case that if the Oilers are willing to part with that much of their future for one player, it should be Karlsson.

It’s also unlikely the players selected in those spots would be able to help the team while McDavid and Leon Draisaitl are still in the respective primes, especially if the Oilers finish near the top of the league for the next three seasons. But for any deal to work, the Oilers will need to send out at least one contract and get the Sharks to retain closer to 40 or 50 percent of Karlsson’s cap hit.

“Whether it’s forwards or defence, it’s my job to be aware of who is available and eventually what the price might be,” Holland said Wednesday on the Got Yer Back podcast on February 8.” We’re dollar in, dollar out, so if we start bringing in people with big cap numbers, we’re going to have to do some real gymnastics here to move people out. When you’re in a LTI situation like we are, it’s much more difficult at the trade deadline.”

I could see the Oilers offering a package of Jesse Puljujarvi, Warren Foegele, top prospect Xavier Bourgault and their 2023 first-round pick for Karlsson. Puljujarvi is still only 24, and all signs point to him being dealt before the deadline, whether it’s to the Sharks or another club. Foegele has performed better as of late, but is overpaid for a bottom-six forward. While the Oilers would certainly prefer to keep Bourgault, who could be a future winger for McDavid, Karlsson gives them a better to win the Stanley Cup right now.

Related: NHL salary cap expected to rise at perfect time for Oilers

That said, this deal hinges on remaining term. Karlsson is signed through the 2026-27 season. If the salary cap climbs as much as it’s expected to over the next few summers, his contract will be easier to stomach. But for an Oilers team with no cap space, they would need his cap hit to be around $7 million.

The Oilers window to win the Cup is wide open, and Karlsson could be the piece that helps them reach their ultimate goal this spring.