There is so much to unpack from Thursday’s announcement about the hiring of Jeff Jackson as the Edmonton Oilers CEO of hockey operations, and there’ll be much more to come, but a couple of things stick out for me this sunny holiday weekend.

First, I can’t imagine a better scenario than what’s been created here by bringing in the 58-year-old Jackson, who has played in the NHL, became a lawyer after his retirement, and earned his front office stripes along the road that led him to Edmonton to work with GM and president of hockey operations Ken Holland.

All that, and Jackson has had a decade-long relationship with the best player on the planet as Connor McDavid’s agent at the highly-regarded Wasserman Agency. They know each other. They respect each other. I can’t think of a similar situation, at least not involving a player of McDavid’s stature. It’s a direct connection to a player who’ll have more say in the fate of this franchise in win-now mode than anybody. It’s having a finger on the pulse of the team.

Second, Jackson is sharp enough to resist the urge to try to prove that he’s the smartest guy in the room in his first 15 minutes on the job before he knows who’s-who and what’s-what – we’ve seen that attempted a time or two. It seldom turns out well.

Owner Daryl Katz wants Jackson here. So does Holland, who we know will be moving out of the GM’s chair soon enough. I could be wrong, but I don’t see a need for Jackson to make a big splash, save for getting new deals done for McDavid and Leon Draisaitl at some point. That just got way easier, no?

About McDavid, Jackson said: “Who in this room doesn’t want him to be an Oiler for life? I think at the end of the day, Connor has three years left on his deal. He, Leon, Nuge, Nursey, they’re all striving to win. I think that’s going to be the biggest driver. Of course, I have a very close relationship with Connor. It’s going to be a different relationship now, but I think ultimately, the goal is to keep this team and this core group together. I think there’s a lot of runway for success for a number of years, so that’s the goal. 

“We’ve spent a lot of time over the years talking about the team and where they’re at. I know with these recent conversations that I’ve had with him as I considered this job, I think he feels like things are in a really good spot. He’s super excited about the season. He’s more dialed-in than ever, which is hard to believe because he’s always that way.” For context, the transcript of Jackson’s media availability is here.

As for putting his stamp on the team, Jackson said: “I’m not coming in to reinvent the wheel with the team. I think, as I said, Kenny’s done a fantastic job of building this culture for the last four years to the point where the team is in a great spot. I hope that I can bring some different views.

“On the agent side of things, you do a lot of your own scouting of young kids. We used analytics, and I know the Oilers do. I’m going to look at all those things and try to be the best in class. It won’t happen overnight, but I’m going to dig in on all of the things that I know. Having the luxury of talking to Connor, I know how good this team is at a lot of things. If we can incrementally get better at some of the other things, I think that’ll make a big difference.”

It’ll take some time to unfold, but my sense is Thursday was a big day for this franchise.

Holland, 67, is a hockey man through and through and has been since he retired as a player and decided against pursuing a career as a vacuum cleaner salesman to join the amateur scouting staff of the Detroit Red Wings in the mid-1980s – it’s true, you can look it up. Being a fossil myself, I’d see Holland in rinks around the WHL in those days.

The rest of his story we know. From there, he climbed the ranks to become director of amateur scouting, assistant GM and later GM. All told, Holland won four Stanley Cups. He joined the Oilers in May 2019 on a five-year deal rather than be kicked upstairs as a senior vice president with Steve Yzerman taking over as GM. He was inducted into the HHOF in the class of 2021.

Holland obviously wasn’t ready to ease into retirement then, but my sense is he’s ready now. His son Brad is an assistant GM here, Jackson’s arrival gives him a season in the final year of his contract to help with the transition. Another Stanley Cup celebration would be the cherry on top of a great career. We’ll see about that.

With Dave Gagner taking over from Jackson at Wasserman as Evan Bouchard’s agent, it sounds like there will be news about his bridge contract next week. I pegged a bridge deal for Bouchard at $3 million, give or take 100K, while others have it higher. Roster size will impact Bouchard’s number.