SUNRISE, Fla. -- Jeff Jackson’s first 10 months as CEO of hockey operations for the Edmonton Oilers have been anything but boring.
“I’ve loved it,” he said during a 1-on-1 sit-down with NHL.com this week. “But it’s been quite the roller coaster ride, hasn’t it?”
It still is.
In the latest chapter of the Oilers' topsy-turvy times, Edmonton finds itself down 2-0 against the Florida Panthers in the best-of-7 Stanley Cup Final and has to hope a shift to the Alberta capital for Games 3 and 4 will turn the momentum around in its quest to win the title for the first time since 1990.
Game 3 is at Rogers Place on Thursday (8 p.m. ET; ABC, ESPN+, CBC, TVAS, SN).
However the script plays out, nothing will come as a surprise given the events of the past season to Jackson, who was hired by the Oilers on Aug. 3, 2023, after being an agent for the Wasserman Agency. His most notable client there: Edmonton captain Connor McDavid.
“When Edmonton first approached me, Connor told me that I would be great for the position but it would have to be a decision I was comfortable with,” the 59-year-old said.
The Oilers, the preseason pick of many prognosticators to win the Stanley Cup, got off to a disastrous start in the Jackson era, going 3-9-1. At that point on Nov. 12, just 101 days into his tenure, he and the management team opted to fire coach Jay Woodcroft and replace him with Kris Knoblauch, who at one time had coached present-day Edmonton forwards McDavid, Connor Brown and Warren Foegele with Erie of the Ontario Hockey League.
Not the way Jackson envisioned his new gig would start. But the move worked as the Oilers, backed by a 16-game win streak under Knoblauch, went on to finish 49-27-6, second in the Pacific Division.
In the postseason, the Oilers have trailed in each of the previous two best-of-7 series, first 3-2 to the Vancouver Canucks in the Western Conference Second Round, then 2-0 to the Dallas Stars in the conference final.
On each occasion, Edmonton came back to win the series. Now the Oilers will have to do it again after scoring one goal in the first two games.
“We’ve faced a lot of adversity this season,” Jackson said. “We’ve shown we’ve responded well to it.”
Can the Oilers do it again? In a wide-ranging interview, Jackson addressed that topic, along with what the future holds for the team, all things McDavid, and his return to an NHL front office after being an assistant general manager with the Toronto Maple Leafs in the mid-2000s.
First off, what do you expect the excitement level to be in Edmonton for the first Stanley Cup Final games in the city in 18 years?
“Well, based on the first three rounds and the excitement around the city, I suspect it will be similar but obviously elevated. They have been waiting for this for a while and we have very passionate fans, so I’m sure they’re going to be hyped up, which will be great for our team.”
What would it mean for this whole journey -- your personal one and that of the team -- if you can come back in the series and end up winning the Stanley Cup?
“Everybody in hockey pursues this, like 365 days a year, so to be in the Final and having a chance to compete, I feel very fortunate. I have a lot of gratitude for the opportunity and we’ve had some good fortune along the way, like when we started the playoffs. There are 16 really good teams in the first round and there's eight really good teams in the second and there's four really good teams in the third. There’s no easy road here. So, our players have stepped up and played extremely well, our coaches have done a great job and I just feel lucky to be here. There are guys who've been in the game a long time who have way more experience than me and have done way better things, and maybe they haven't gotten here because of circumstance. I just feel I feel very fortunate.”
Looking back, any second thoughts on the decision to take the position?
“It was was a big decision for me to leave what I was doing. We built up the agency up to be, I think, one of the top groups and I really, really enjoyed it. I loved my clients and their families. And so it was not an easy decision. But once I made it I was all in. And I think that being in my role sort of suits my personality. I’m pretty calm. You have to think big-picture with this job. I don't get too excited, day to day, about success or failure because it all evens out. So I’ve really enjoyed it. I mean, I think I stepped into a situation where the team was and is very good. And now we're performing to that expectation where many expected us to challenge for a Stanley Cup even before the season started. And that's why we're here.”
How did you first forge a relationship with Connor?
“He was 15 years old, so he was a young kid, first year in the OHL, on not a very good team at the time. All I would say about Connor right from the time I met him was that he wanted to win and he was willing to put the time in and try to be the best. He had a high degree of respect for the game and didn't want to cheat anything. He didn’t want to be handed anything. He didn’t want to be anointed. I loved the attitude. The humbleness and the work ethic combined is a recipe for success. He’s just a quality kid, a young man who's who's mature in every way. But even when he was 15 he had a maturity to him and it's just sort of evolved. It was a pleasure being his agent for all those years and it's nice to be around him every day. Now it’s just a little bit different, right?
In what ways?
“I mean, he doesn't come to me to vent or talk about things that we used to talk about. That's now the role that Judd Moldaver plays in his career. Judd stepped in and has done a great job as his agent. And so now it's more just like there's a comfort with him and I from a long relationship. It’s very casual. It's very mellow. We don't huddle up and have meetings and stuff."
What’s the relationship with your players in general?
“I don't hang out with the players but I do cross paths with them. I think it's an important thing for the senior management in an organization to be around the players and be able to talk to them about everything. I like be be accessible, right? So, that's how I ended up having my chats with them.
What went into the decision involving the coaching change? And why Kris Knoblauch?
“I had lots of dealings with him through a bunch of dealings with him, including Connor, both in junior and the pros. And what I saw as an evolution of him as a coach, and the feedback from all my clients who played for him, was that he was a fantastic coach, a great communicator and someone who was very calm, super prepared, strategic and calm on the bench. He never gets flustered so he never loses players on the bench. The game is fast and there’s a lot of stuff going on, so I think being calm back there is important for the team’s psyche. So, all of those things combined. I just thought he’s put his time in and that he would be what we needed here, given our personnel and where we were as a team, struggling at the time. He’s done a great job. It was a hard decision at the time to let Jay and (assistant) Dave [Manson] go at the time because they’re both great coaches but we needed something to change at the time. And now we’re here.”
Finally, how frantic is it going to be with the team in the Final, the NHL Draft taking place at the end of the month, and free agency beginning on July 1? That’s a lot of things on your plate all at once.
“We were hoping for an extended playoff run so we prepared in case it came to fruition. And it has. We’ve been preparing simultaneously for those things. Our amateur scouts have done great jobs. We’ve been talking with agents about renewals with some of our minor league guys. We’ve been working in tandem with all those things you mentioned moving forward and mapping everything out. We’ll be prepared. It’s a short turnaround but we’ll be fine.”
