One of Ken Holland’s top priorities this summer is creating salary cap room.

The Oilers need to figure out new contracts for a trio of restricted free agents and their sweep at the hands of the Colorado Avalanche in the Western Conference Final made it clear the team needs upgrades in order to hang with the league’s elite.

As of right now, the Oilers are only about $7 million from the salary cap ceiling. They’ll get some help from the LTIR with Oscar Klefbom, but that won’t be enough money to re-sign Jesse Puljujarvi, Kailer Yamamoto, and Ryan McLeod along with finding an upgrade in net and finding someone to score goals like Evander Kane did.

One of the ways that Holland could open up some wiggle room right off the hop this summer is by buying out the remainder of Zack Kassian’s contract.

Holland signed Kassian to a four-year, $12.8 million extension back in January of 2020 when he was thriving alongside Connor McDavid on the team’s top line. Through the first two years of that contract, Kassian has scored just eight goals and 24 points over 85 games and has been passed on the depth chart by both Puljujarvi and Yamamoto.

If the Oilers buy Kassian’s contract out, they’ll save money over the next two years by essentially borrowing from the two years after that…

While this would certainly make life a little bit easier in the short term, the Oilers have been plagued by having dead money on the books for years, and buying out Kassian would just continue the trend of kicking the problem down the road.

The Oilers have created dead money in each of the last six off-seasons. They bought out Lauri Korpikoski in 2016, Benoit Pouliot in 2017, Eric Gryba in 2018, and Andrej Sekera in 2021. They traded Milan Lucic for James Neal and retained part of his salary in 2020 and then bought out Neal in 2021. They have roughly $4 million in dead money counting against the cap for 2022-23 from Lucic, Neal, and Sekera.

Now, I’m certainly not here to suggest buying out Neal or Sekera was a poor idea, but it’s worthwhile to pause and look at how much dead money the Oilers create for themselves and ask if there’s a better solution.

If the reports about the Philadelphia Flyers offering their vacant coaching position to John Tortorella are accurate, there will be at least one team out there who might view Kassian as an asset. If that doesn’t work out, there are a handful of teams around who are just trying to reach the salary cap floor and will take bad contracts off of the hands of other teams in exchange for a sweetener.

Last summer, the Arizona Coyotes netted themselves a whole bunch of draft picks by taking on a pair of veterans from teams who were struggling to stay under the cap.

The New York Islanders sent two second-round picks and a conditional third-round pick to the Coyotes in order to dump Andrew Ladd, who had two more years left on his contract at $5.5 million. The Philadelphia Flyers gave up a second- and seventh-round pick to get rid of Shayne Gostisbehere, who had two years left at $4.5 million on his deal.

$3.2 million for two years isn’t a huge price tag and Kassian can still play, so he certainly wouldn’t cost more to dump than either Ladd or Gostisbehere, but the challenge for the Oilers is that they already don’t have a second-, third-, or fourth-round draft pick this year. If they’re going to attach a second or a third to dump Kassian’s deal, they’d have to pluck one from their pool of 2023 draft picks.

Another thing to consider is attaching Kassian to the 2022 first-round pick, which will be No. 29 overall, and using his contract to offset the cost of bringing back a player who can contribute now. Kassian would weigh down the value of the first but the Oilers have a deep enough farm system to withstand the blow. That said, Holland hasn’t yet parted with a first-round pick since he arrived in Edmonton so it’s hard to say if he would look for such a deal.