Oilers CEO Jeff Jackson on working with GM Ken Holland: 'What I’ve really liked since I joined is that we’re collaborative'

The trade deadline for the 2023-24 NHL season is just over one month away and it’s very difficult to say exactly what the Edmonton Oilers will do.

This is a team that’s in win-now mode with a Stanley Cup or bust mentality and coming up short will result in the season being viewed as a failure. With that in mind, the Oilers should obviously be looking to improve their team ahead of what should be a deep playoff run.

But this is also a team that’s in a difficult spot when it comes to making upgrades. The Oilers are pressed right up against the salary cap ceiling and just about any addition will require a subtraction from somewhere else on the roster.

Earlier in the season when the team was off to an inexplicable 3-9-1 start, the pressure to swing a deal for a goaltender or a shutdown defender or a veteran forward was much more intense. Since making a game-changing trade in November is nearly impossible in the modern NHL, head coach Jay Woodcroft and assistant coach Dave Manson ultimately took the fall.

Since Kris Knoblauch and Paul Coffey took over behind the bench, the Oilers have put together a staggering 26-6-0 record, highlighted by a historic 16-game winning streak. Things aren’t as desperate now, the areas of need aren’t quite so clear, and removing any member of the group that’s rattled off wins in 24 of 27 games together comes with some risk involved.

Jeff Jackson, the Oilers’ CEO of Hockey Operations, spoke to Daniel Nugent-Bowman of The Athletic last week and noted that upper management is taking team chemistry into account as they plan for the trade deadline.

“We just spent three days together here in Edmonton — the entire pro scouting staff. It was very productive.

This is the time of year when all the teams do this. You sit down and you figure out what essential things you feel might (be) a need, or (how) you can make yourself incrementally better. That’s the process that we’ve done now. We’ve pinpointed some things, and then we’re going to follow up.

There’s still time before the deadline. The issue right now is there’s lots of teams that are still in the playoff hunt. Nobody’s really folding up the tent to start selling assets at this point. We have to monitor that. When they’re ready to make a deal, if the pieces fit, then we’re ready to do it.

We’re also cognizant of the fact that messing with chemistry on a team sometimes is a dangerous thing. But if you get the right pieces, and you do it the right way — as long as you’re getting better, and you’re not messing with culture — we feel confident that we can make a couple moves that would make us better.”

Jackson was hired by the Oilers in August following a career as a player agent that spanned over a decade. His first client was Sam Gagner, who was with the Oilers at the time, and he helped grow Wasserman Hockey, which represents Connor McDavid, into one of the most respected agencies in hockey.

With general manager Ken Holland in the final season of the five-year contract that he inked with the Oilers back in June of 2019, many questions have come up in regards to who has the final say when it comes to hockey operations decisions for the Oilers. Jackson noted that Holland is still the team’s general manager and that the two have a strong working relationship.

“Ken Holland is the GM of the team. What I’ve found and what I’ve really liked since I joined is that we’re collaborative.

We talk multiple times every day. We throw ideas off each other. We throw ideas off of Kris Knoblauch and Bill Scott and Keith (Gretzky). The group is very good that way. We’re not sitting in our own offices trying to come up with scenarios and execute them ourselves.

Ken’s a general manager. Brad (Holland) is an assistant GM who’s the head of pro scouting. He’s got a big voice, too. The entirety of the group works on all these things at this point.”

During the six months that Jackson and Holland have worked together, the biggest move has been the coaching change, followed by the addition of Corey Perry through free agency. There’s been plenty of speculation Holland will retire once his contract is over this summer, which could push him to be very aggressive ahead of this year’s trade deadline so that he can finish his career as a general manager in the NHL on top.