The Oilers' CEO and president of hockey operations chats about the expectations in Edmonton, working with Stan Bowman and his relationship with McDavid
The Edmonton Oilers' CEO of hockey operations ranks 44th among the 100 People of Power & Influence in hockey.
Jeff Jackson, 60, joined the Oilers in 2023 after working at Wasserman Hockey as an agent for Connor McDavid, Evan Bouchard and more.
Since then, the Oilers made it to the Stanley Cup final in back-to-back years, and he hired Stan Bowman as the team's new GM. The front office negotiated a two-year contract extension worth $12.5 million annually with McDavid.
Ryan Kennedy spoke with Jackson for The Hockey News' Money & Power 2026 hockey business annual, released in early January.
THE HOCKEY NEWS: You've been in your role for a couple of years now, and the Oilers have made the Stanley Cup final both times. Do you enjoy the expectations of working in a market like Edmonton?
JEFF JACKSON: Obviously, I was pretty close to the vibe and the way the team was viewed when I was on the agent side, having Connor McDavid and Evan Bouchard as clients.
When I took the job, the expectations were high, and I knew that going in. We had a lot of good pieces two years ago, and every team morphs. You can't bring the same team back for a bunch of reasons, usually related to contracts and the cap.
But to answer your question, yes, we have a very passionate and knowledgeable fan base that has a history that is very important to the city. We're trying to write our own history, and we've gotten very close two years in a row. We haven't gotten the job done yet, and, obviously, that's going to be the goal, to get back there and get over the hump.
THN: Your first management job was in another hockey-mad market in Toronto. What did that initial experience mean to you in terms of working in the NHL in that capacity?
JJ: That experience being an assistant GM in Toronto was invaluable, even though everything has changed in the media landscape. Social media, podcasts, it's a lot different than it was from 2006 to 2011.
But the pressure of the market was something I learned you had to deal with. That's where it ties in, where you don't get too high or too low.
Even when we had a 16-game winning streak and an 11-game winning streak a couple of years ago, you try to stay on an even keel. If you're going through a funk as a team, obviously, you can't have rose-colored glasses. You have to look at what's wrong and try to fix it.
But when you're managing a team, and Stan (Bowman) and I are very much alike this way, you can't react to people pounding on the table calling for trades.
JJ: As an agent, you get a full view of the league. You have clients on various teams. You understand how a team operates on a day-to-day basis, what their development programs look like and how those are executed. You get an inside view, and it's through a combination of your relationship with the team but also from your clients. You get a lot of information from clients because they're very vocal about what they like and don't like.
So as an agent, you can very clearly see which organizations do things in an elite manner. And not all do everything great, but some do certain things well. You understand the player development arc really well because you're recruiting kids young, and you have to do your due diligence. So that filters into amateur scouting and free-agent signings.
THN: It occurred to me, you might have negotiated with Stan Bowman in the past when you were an agent. Why do you think you two work so well together now?
JJ: When I was an agent, I always thought Stan was an excellent GM. I first got to know him when I was an AGM and he was an AGM in Chicago. As an agent, I had Alex DeBrincat in Chicago, and we did his second deal together.
But it was more than just the contract; it was the way Chicago and Stan did player development. The emphasis they put on cutting-edge stuff, whether it was video, virtual-reality work or analytics, Stan was doing stuff 10 years ago that I don't think a lot of teams were doing.
With Stan, I knew the type of person I was hiring and how good he was as a GM, how he thinks things through. We're both similar in personality. We're both calm and don't let things rattle us. I enjoy working with him immensely, and I think he's one of the top guys in the league.
THN: Speaking of top guys, your captain is Connor McDavid, who you've known for years from representing him. What kind of growth have you seen in him throughout your relationship?
JJ: The spotlight has been on Connor since he was a young teen, and there were times when he was a young NHLer or finishing junior where he maybe didn't feel comfortable with the spotlight on him.
The biggest thing for me is that he matured into an incredible leader who understands his role in the game and the obligations that come with it. And he's comfortable with it now. He's OK to acknowledge that he's the best player in the game, and with that comes pressure, responsibility and obligations away from the ice.
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