The Oilers Are Stuck In A Cycle Self-Correction

It’s no secret that the Edmonton Oilers are in win-now mode, and that mode has shifted to pure desperation as they enter the final two years of superstar captain Connor McDavid’s current contract. It’s completely understandable that the Oilers have spent years sacrificing future assets to win now, given the window they are in with the best player in the world on their roster. However, that desperation to win now has led Oilers management to make aggressive moves, many of which have been disasters. Their desperation has often forced them into awful trades or signings, sometimes to undo ill-advised moves or simply because they thought they had to fix a roster hole. This line of thinking has painted the Oilers into the corner they currently find themselves in, out of the playoffs in the first round, with an unhappy superstar and a fanbase left shaking their heads.

Edmonton has repeatedly paid a premium to plug holes in the lineup or to undo prior mistakes in player acquisition. This has been especially true for the Oilers’ depth, defensive reliability, and secondary scoring, where they’ve either ignored the problem or acquired players who created a hole. From the outside, it feels as though Edmonton is constantly chasing fixes, reacting to structural roster issues rather than building a roster with any semblance of a long-term plan. As mentioned, the Oilers sacrificed future assets to win now, but they’ve also repeatedly spent additional assets to fix the holes their prior aggressive moves often created. This type of thinking is often called the sunk cost fallacy, in which someone doubles down on a bad decision because too much has already been invested.

There are few better examples of Edmonton’s reactionary thinking than the Jason Dickinson trade with the Chicago Blackhawks prior to this year’s NHL Trade Deadline. The Oilers released a video of the team’s management group discussing the potential trade for Dickinson. Although the clips were just 2 minutes, they painted a picture of a management group with a relatively shallow, short-sighted understanding of the trade they were trying to make. Effectively, Oilers general manager Stan Bowman was trying to plug a hole on his roster that he thought he’d filled at last year’s trade deadline with the trade for Trent Frederic, only to see Frederic implode this season after signing an eight-year extension last summer. Simply put, the trade felt like damage control stemming from previous poor decisions with Frederic and the free-agent signing of Andrew Mangiapane, who was included in the Dickinson trade as a salary dump after a poor showing in Edmonton.

Mangiapane is a clear example of Edmonton’s mismanagement and inability to find the right pieces for the right roles. Signed to a two-year, $7.2MM deal, the Oilers hoped that playing alongside their skilled players would reignite the offensive side of Mangiapane’s game; however, that did not happen, and he was traded to the Chicago Blackhawks less than one year into the deal.

As good an example as Mangiapane is, there is no better example than goaltender Tristan Jarry. Jarry was acquired from the Pittsburgh Penguins in December, when the Oilers were in desperate need of better goaltending. The trade came less than three months after Bowman had stated that he “Liked where Stuart Skinner’s game was.” Bowman’s comments came on the heels of a summer with no movement in the Oilers’ crease, despite it being a clear area of weakness.

Skinner began the season with the Oilers, going 11-8-4 with an .891 SV% and a 2.83 GAA. At the time of the trade, Skinner was ranked 32nd in Goals Saved Above Expected, while Jarry was 22^nd. Edmonton hoped that moving Skinner for Jarry would be a massive upgrade and even included defenseman Brett Kulak and a second-round pick.

The trade was a colossal disaster for the Oilers, as Jarry reverted to his recent form, going 9-6-2 in 19 games with Edmonton, posting an .857 SV% and a 3.86 GAA. Jarry wasn’t just bad in Edmonton; he was among the worst netminders in the league after the trade.

Had Edmonton management simply addressed the issue last summer, they likely would have avoided a trade for Jarry, which will have repercussions for years, as Jarry has two years left on his contract, a deal that is effectively buyout-proof.

The Oilers’ asset recycling continued with the Jarry trade and has become an alarming trend for a team that is shutting its own contention window with each passing season. The Oilers had a clear need to upgrade their roster construction last summer, particularly their goaltending and defense. Instead, they prioritized adding toughness, veterans, and depth scoring, and the results this past season speak for themselves.

The team clearly (and correctly) has a mandate to win now because of the presence of McDavid and Leon Draisaitl, but that urgency has distorted management’s decision-making, prompting panic move after panic move in hopes of catching lightning in a bottle. Management often overvalues urgency and undervalues patience, particularly in player development and salary-cap management.

A persistent narrative in Oilers fandom is that the team is one piece away, but for a team that constantly patches holes mid-season, that logic seems flawed and generally indicates poor organizational planning. You could certainly point to trades and moves in a vacuum and say they worked, but when you zoom out and look at the broader picture, a pattern starts to emerge.

The pattern is that the Oilers have rarely built forward and have spent most of the McDavid/Draisaitl era trying to escape the consequences of their past bets. If the Oilers want to finally bring a Stanley Cup back to Northern Alberta, some hard conversations need to be had among management to break this cycle.