EDMONTON — Hiring Ken Holland as a general manager four years ago was a relatively easy and rather obvious decision. So was Peter Chiarelli before him, as the Edmonton Oilers filled their vacant GM chair with two established and available names of the day.
There is a level of sophistication to this Jeff Jackson hire, however, as the Oilers surprised the hockey world with an acquisition on Thursday that takes Daryl Katz’s organization down a path it has always been reticent to tread.
Jackson has never been in the corner office, as he will be as the new CEO of hockey operations in Edmonton. But he did work as an assistant GM and director of hockey operations for the Toronto Maple Leafs for four years — so he knows hockey ops.
Sure, he was an ex-pro, like almost every other significant front office hire this team has ever made. But he earned a law degree and became one of hockey’s most successful agents in the years since — something that most of the old Glory Years Gang did not do when the game passed them by.
And then there is the cherry on top: He was the only agent Connor McDavid ever had.
“Connor was 15 when I started working with him,” said Jackson.
The facile way to look at this hire is that Jackson’s presence will ensure that McDavid signs his next contract with the Oilers on July 1 in 2025, with this one expiring after the 2025-26 season. That Jackson will sit in a chair until McDavid re-signs, McDavid will be so loyal to the only agent he’s ever had, and we’ll all live happily ever after in Edmonton the way they have in Pittsburgh with Sidney Crosby.
But there is so much more to it than that.
“We've spent a lot of time over the years talking about the team and where they're at,” Jackson said of he and McDavid. “The recent conversations that I've had with him … he feels like things are in a really good spot.
“He's more (focussed) than ever, which is hard to believe because he's always that way. Leon (Draisaitl) is living in Ontario and working out with him. Zach Hyman is there … and I think that they're all coming back (to Edmonton) early from what I understand. So, he's got these guys in a good spot, and himself (too). He feels really good about where everything is.”
When Edmonton lost Game 6 to Vegas, in a Round 2 series in which they led in every game, there was obvious disappointment. But among the core group here — McDavid, Draisaitl, Hyman, Darnell Nurse, Mattias Ekholm — emotions boiled while watching Vegas win a Stanley Cup.
The feelings among the group, we hear, are two-fold:
They are indeed a legit Cup contender, and the lessons that need to be learned along the way have all been taught, the report cards returned.
Starting now, as Draisaitl said after the Vegas series: “It’s Stanley Cup or bust.”
“If that’s the players’ mentality now, that's great,.” Jackson said. “They’re not satisfied with getting to the semis or final. They want to win — that's how I interpreted (the Draisaitl quote) when I heard it. That's what their mindset is coming back, from what Connor has been telling me.”
This is an organization in need of a succession plan, and now Jackson sits atop the hockey pyramid in Edmonton. Holland enters the final year of his contract, and at age 67 is ready to retire from the grind of running a team. Former CEO Bob Nicholson is 70 and also easing into retirement.
This organization needed fresh ideas, a younger lead horse, and they got both with the cerebral Jackson, the 58-year-old who has peered into the hockey world from pretty much every angle.
This last one, however, is the biggest.
How to take a team that has played five playoff rounds over the past two springs, and turn it into a Stanley Cup winner?
“I have had the distinct pleasure the last eight years of watching this team very closely, with Connor being a big part of that. I've spent a lot of time in Edmonton. I've watched this team evolve,” he said. “It's a unique opportunity. I don't think that I would have you gone anywhere else. I wasn't looking to leave the agent business.
“The fact that Connor was involved, and the team that Kenny's put together is on the verge of some great things…”
Now, he must chart the next steps.
It starts with overseeing the extension of Leon Draisaitl in July of next year, and crafting a team that McDavid simply can not leave when it’s his turn to make that decision.
Then, and only then, can Jeff Jackson become both the man who kept Connor McDavid in Edmonton, and the guy who presided over the return of the Stanley Cup.
It’s an opportunity that few will ever have, and one where even less would succeed.
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