From Cup Contenders to Questions: Oilers’ 2024 Offseason Started Slide

The Edmonton Oilers entered the 2024 offseason riding the momentum of a Stanley Cup Final appearance, but made a series of costly missteps that have already begun to haunt them. One of the Oilers’ biggest missteps was allowing Jeff Jackson to run the draft and free agency before hiring Stan Bowman. Jackson made major roster decisions, leaving Bowman to clean up the aftermath and manage a roster he didn’t get to put the first stamp on after Ken Holland was removed from his position.

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The Oilers were feeling good about how many players were eyeing them up in free agency. They were the belle of the ball, and player agents were reaching out. With the cap space they did have, the Oilers made two costly mistakes.

They signed Jeff Skinner and Viktor Arvidsson in free agency. Both came with past success, but there were questions about fit and declining numbers. Even still, the Oilers paid them well and gave them no-move clauses. Both failed to produce as top-six forwards. Skinner was rarely used and not re-signed; Arvidsson was eventually traded to Boston.

In a head-scratching move, Edmonton also signed defenseman Josh Brown to a three-year deal. The veteran tough guy barely played and didn’t justify the commitment.

As a result of the signings, cap space issues opened the door for the St. Louis Blues to successfully offer-sheet Philip Broberg and Dylan Holloway. Broberg wanted out due to a lack of opportunity, and Holloway, despite his upside, was overlooked in favor of the new veterans. Losing two young, ascending players was a significant setback.

Their Own Players Were Not Handled Properly

One of their errors — which didn’t seem like a massive issue until this summer — was failing to sign Evan Bouchard to a long-term extension. After a strong playoff performance in 2023, the Oilers hesitated, likely fearing an inflated market value. However, Bouchard only got better, and the rising salary cap made it impossible to get a team-friendly deal. As a result, they signed him a year later to a four-year, $10.5 million AAV contract — full value — which contributed to a tight cap situation and limited their ability to retain key depth players.

Related: Bowman Breaks Silence on Bouchard Heat and Massive Extension

Lastly, the Oilers made no goaltending upgrade, opting to stick with Stuart Skinner and Calvin Pickard. Though not solely responsible for their playoff exit, the position remains a concern — and no obvious upgrades have since materialized.

Looking back, the 2024 offseason now appears to be a missed opportunity for a team that was right on the brink. The cap is rising, but the Oilers appear to be stagnant in their development and roster improvement. They’ve lost key depth forwards, are going with untested rookies (which may turn out great), and they still have salary cap issues.

What’s most problematic in all of this is that Connor McDavid is watching every move. The Oilers need to be making strides to get better, not moves that make them worse. If they keep doing so, how long will McDavid want to stick around?

Next: What McDavid Would Make If He Played in Another League