Oilers’ Front Office Feeling Pressure From All Sides

On the most recent 32 Thoughts: The Podcast, respected NHL insider Elliotte Friedman pulled back the curtain a bit on what’s been happening with the Edmonton Oilers. Most notably, Friedman revealed the level of displeasure that Oilers owner Daryl Katz had with how the Oilers’ 2025-26 season ended and how Katz might’ve had some influence in the decision to let go of head coach Kris Knoblauch.

Friedman mentioned, “I think he (Katz) was so upset at the way this season ended. I think he was a driving force. I don’t think you can underestimate the role he played in making his feelings clear that significant change needs to happen.”

Oilers’ Ownership in Stanley Cup or Bust Mode

Friedman went on to say, “There is great organizational pressure to win now for a lot of reasons, including the fact that Connor McDavid is only under contract for two more years. I think the owner’s feelings were a very big part of this. That after a season like this one, you have to look at what happened, you have to make hard decisions, and you have to say, ‘We’re going to make what we think are the best decisions for our organization so that we can win.’”

What Happened After News Leaked About Bruce Cassidy

Some people were upset that the Oilers had gone behind Knoblauch’s back while searching for a new head coach after news leaked that they wanted to talk to former Vegas Golden Knights head coach Bruce Cassidy. Others, like NHL executive and player agent Brian Lawton, had a different take. Lawton told Bob Stauffer on Oilers Now on 630 CHED on May 12 that, “I don’t see it as shocking as most people may, and that sounds a little bit (cold), but it’s also just part of the business.”

Lawton went on to say, “Stan Bowman is doing what he should do, which is turn over every rock as to how he can possibly improve, in this case, the organization, the coaching…What makes this awkward or uncomfortable is that there’s no secrets anymore.”

Does the Oilers Organization Have a Target on Its Back?

As an Oilers fan, I’d love to see McDavid, Leon Draisaitl, and Ryan Nugent-Hopkins win a Stanley Cup in an Oilers uniform. I see an owner who is passionate about his team and is willing to spend money to help the Oilers win. I also see an organization with a target on its back. It’s still unclear how the news got out about the Oilers’ interest in talking to Cassidy. This isn’t an isolated incident involving bad blood between organizations, either.

Go back to August 2024 when the St. Louis Blues made their double offer sheet to Dylan Holloway and Philip Broberg. Blues general manager Doug Armstrong knew the exact day to strike because if he had waited one more day to make the offer sheets, the Blues would’ve had to give the Oilers first-round draft picks, rather than the second- and third-round picks the Oilers received. I’ve always wondered if Armstrong’s friend, Ken Holland, was still the general manager of the Oilers that offseason and whether these offer sheets would have happened.

Where Do the Oilers Go From Here?

There’s no guarantee the Oilers will land Cassidy as their next head coach. If they don’t, could Craig Burube or Peter Laviolette get the job? You have to believe that with the clock ticking on McDavid’s contract, the Oilers will go after a veteran coach with a Stanley Cup pedigree to replace Knoblauch. As for other offseason moves, such as a new goaltender and third-line centre, we’ll just have to wait and see. Regardless of whether you agree with the Oilers’ recent decisions or not, you can’t say that things are boring in the Alberta capital.