The Oilers had just gone through an ugly campaign where both coach Todd McLellan and general manager Peter Chiarelli were gassed mid-season. They missed the playoffs by 10 points, an annual tradition then.

In fact, Edmonton had missed the playoffs 12 of the last 13 seasons.

Despite having franchise-changing pieces – for real this time – in Connor McDavid and Leon Draisaitl, the organization still operated suspiciously. Things were weird with Wayne Gretzky in the fold, the lingering influence of the Old Boys Club, and how decisions were ultimately made.

Who was deciding what?

Katz felt it necessary to show up and address the criticisms head-on. Although we were all initially distracted by his health issues and different appearance, Katz went out and delivered a State of the Franchise speech.

He didn’t sugarcoat it:

“We have not delivered on the promise we made to our fans in recent years,” he said. “You know it, and I know it, and we all know it.”

In comes Jackson

Since then, Katz has not been seen or heard from, at least not in the hockey sense.

But to his credit, the team has taken on a sense of seriousness and legitimacy in the hockey world, which was foreign to that point. There were no more whispers of the Old Boys Club, Red Wine Summits, or Katz intervening on major decisions like Nail Yakupov being drafted first-overall in 2012.

The last time a Katz appearance would’ve made sense would be August 2023, when Jeff Jackson was introduced as the CEO of Hockey Operations, as Bob Nicholson was stepping away.

Holland sat beside him in a vaguely awkward way. “Look, everyone, here’s my new boss, who just happened to be employed by Connor McDavid a few days ago!”

President and general manager, Ken Holland, right, introduces Jeff Jackson as CEO on August 3, 2023.

That was a little strange, in retrospect. But who can argue with hiring McDavid’s agent? After all, he had negotiated the initial eight-year extension in 2017.

Jackson said Katz and Paul Coffey approached him for the gig. Now he would report directly to Katz while Coffey would help him, acting as a special adviser.

That would change by November when a poor start cost Jay Woodcroft his job, and Kris Knoblauch was introduced as coach. Jackson and Coffey were there, alongside Holland, to introduce him.

Coffey would also step behind the bench, the first time in a coaching capacity since the disastrous “skills coach” period of 2018, and of course, again in 2026.

Fast forward five years after Katz’s speech (and two head coaches), and the Edmonton Oilers were in Game 7 of the Stanley Cup Final. They would be within reach of ultimate success twice in a row.

Their plans were oh so close. They were truly a coin flip away from the Cup.

Bowman, Knoblauch

After not so much a steady descent but an eye-opening toss off the mountain peak to conclude the 2025-26 season, the book is set to close on Connor McDavid’s twenties, and he and the Oilers are still without a Stanley Cup.

I bring up this not-so-fond anniversary because this off-season feels as critical as when Katz made his appearance in 2019.

Not in a doom and gloom way. But in the magnitude of impact on the long-term future of the franchise.

At that time, the Oilers were still figuring out how to be involved in the post-season mix. They took those steps. Now the Oilers have to figure out how to not only stay in contention, but climb the mountain again, and this time reach what’s eluded them.

But who gets to help guide that journey? And what steps taken on the way up are part of the reason they fell?

So far, the focus has been on Kris Knoblauch and Stan Bowman.

To what extent should they be blamed for the Edmonton Oilers’ setback season? How does the blame pie chart get separated between the general manager, head coach, and the players?

Since Frank Seravalli reported on Thursday that a coaching change is “more likely than not” and that front office isn’t safe either, there are whispers in the air of change.

Just how deep do they go?

What is clear through free agent signings of the past two years, some by Jackson and some by Bowman, is there’s a disconnect on what types of players the Oilers are acquiring and how they are deployed.

The gamble

Jeff Jackson’s hiring, which signalled the end of Ken Holland, is a key reason why the Oilers are where they are today.

And don’t get me wrong, the Oilers got unlucky. By going as deep in the playoffs as they did but ultimately losing, Jackson had little time to replace the GM before consequential decisions on the roster were going to be made.

This is where you insert the Dylan Holloway and Philip Broberg discussion, for instance.

But Jackson’s free agency moves, which were lauded at the time, signalled the team pushing in chips to win right bloody now. On paper, the 2025 roster was absolutely stacked with UFAs Jeff Skinner and Viktor Arvidsson in the mix, plus the re-signings.

It didn’t prove that way, but despite it all, the Oilers were back in the Final, and had mollywhopped the Golden Knights and Stars in back-to-back rounds.

Jackson’s decisions shaved the longer-term prospect of winning.

To their credit, the Oilers tried to get ahead of Ken Holland’s contract expiring and his retirement, which lasted all of 11 months, and help the McDavid re-signings procedure.

“Who in this room doesn’t want him to be an Oiler for life?” said Jackson in 2023.

Being McDavid’s agent and all, I don’t think it’s a stretch to say that part of Katz’s thinking in bringing in Jackson was to secure McDavid again for as long as possible. Jackson did help succeed in getting the first of the two, Leon Draisaitl, on board for eight seasons in September 2024. McDavid’s was only two.

So, in the most real way since being drafted, Daryl Katz’s biggest asset is in jeopardy.

Katz’s McAsset

I believe Katz wants to win a Stanley Cup. He is as big an Edmonton Oilers fan as there is and has put up gobs of money to show it. But his most valuable and volatile asset is Connor McDavid. I believe that keeping him for as long as possible is his biggest goal.

There is a ton of overlap between keeping McDavid and winning a Stanley Cup, obviously. But where there isn’t an overlap, it will provide answers on what the organization decides in the next few weeks and months.

Money still has to be a factor, no? Are prior relationships seen as so important?

Sportico ranked the Edmonton Oilers as the fifth most valuable franchise in November, worth some $3.1 billion USD. That’s more than the Boston Bruins, Chicago Blackhawks, Philadelphia Flyers, and Detroit Red Wings.

This could create a success formula for a sports team owner that looks like this. Connor McDavid + Total Infrastructure Project + Competitive Hockey = $$$.

The Ice District project, with its level of investment by the Oilers Entertainment Group, City of Edmonton, and Alberta Government, is in the magnitude of billions.

With that said, playoff ticket prices went up again before the 2026 post-season. I know multiple season ticket holders who felt hounded to renew and spend, but couldn’t justify the cost. Are corporate sponsorships firm?

Katz suing the Boyle Street Community Group in 2024 was the last time he was really in the press. Later, they’d come to terms and put the publicity of the homelessness situation behind them.

Let’s also not forget that, as viewers, we were subjected to the greatest level of hockey propaganda ever seen on a broadcast, as the Oilers Community Foundation 50-50 ads were mentioned at every intermission, without fail, after the reports of where certain monies in that other 50 were going.

The salary cap is also rising by $8.5 million, but there’s no question whether the Oilers will spend to the cap if they can, because again, Katz has helped transform the organization to a seemingly “big market.” That isn’t always reflected in the types of players who agree to come to Edmonton, but the surrounding infrastructure and spending are there.

So what’s on his mind?

I don’t have sources within the organization. Not am I trying to be unnecessarily negative. I have no bloodlust for any particular person.

I’m approaching this by riffing as an outsider, trying to look backward to determine what might happen now. This moment in Oilers history feels like it requires the full attention of everyone involved, especially the man who signs everyone’s cheques, Daryl Katz.

While the discussions about which pending free agents should be re-signed, and what position group needs the most attention (goaltending, in my opinion), I can’t help but try to look for the throughline over several years and realize how we got here.

If prior history is true, Kris Knoblauch is fired, and maybe there’s more to come.

I don’t expect Katz to appear or speak any time soon. But this is the type of moment that could warrant it, or at least, we’re approaching that moment.

Strange things of old have started to happen again. Paul Coffey has floated throughout the organization as an adviser, then an assistant coach, a man who stepped away and then returned after being asked. By whom?

A GM and CEO are at odds with a coach over their free agent signings. Two star players are concerned about the direction of the team.

The “Summer of Jeff” and his wagers came close but didn’t work. And part of the reason the Oilers are where they are is because of that off-season.

How bad does it look that Draisaitl lists off names like Warren Foegele, Ryan McLeod, Cody Ceci, and Vinny Desharnais from that team unprompted at his exit interview?When has a player ever talked about ex-teammates from over a season ago and pointed to those decisions as a mistake?

I don’t remember.

So here’s what I’d say.

There is legitimate anxiety about the state of the franchise for the first time in a long while. How did they get here, and how do they move forward? At the end of day, with all that comes with being the owner of the organization, the many layers of decisions, what’s on Daryl Katz’s mind?

Where are we at here with the Edmonton Oilers? That’s what I want to know. Then we can talk about free agents, bad contracts, goaltending, and the whole bit.

Michael Menzies is an Oilersnation columnist and co-host of PreGaming and Oilersnation After Dark. He’s also been the play-by-play voice of the Bonnyville Pontiacs in the AJHL since 2019. With seven years of news experience as the Editor-at-Large of Lakeland Connect in Bonnyville, Menzies collects vinyl, books, and stomach issues. Follow him on X at Menzies_4.

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