August 20, 2023 by Ryan Lotsberg

Jeff Jackson was hired by the Edmonton Oilers to become the team’s new CEO of Hockey Operations on August 3. Jackson was an Assistant General Manager with the Toronto Maple Leafs from 2006-2010. He made the transition to being an agent when he launched his own agency in 2010. Jackson was integral in the creation of Wasserman Hockey, which has become a renowned agency.

We know that Jackson was Connor McDavid’s former agent, and we’ve made the quantum leap that their relationship will likely have a positive impact on the likelihood of McDavid signing a long-term contract extension with the Oilers. Jackson is a respected member of the hockey community, and he will bring more to the table than just his relationship with McDavid. 

My goal in writing this piece is to understand more about Jackson’s potential impact on the Oilers hockey operations department. I can only work with existing data, and the best place to start is the press conference that Jackson held with Ken Holland the day he was hired.

Ryan Rishaug from TSN asked Jackson about his approach to handling the impending decision to be made about the General Manager position once Holland’s contract expires at the end of the coming season. This was Jackson’s response:

“I guess part of what my role is going to be is looking at the entirety of the organization. I think for me right now my focus is starting today, spending a lot of time with Ken and learning a little bit more about the organization. I’ve been around the team for eight years, but I don’t know the inner workings of the team. I don’t know some of the… I don’t know all the scouts, I don’t know how Ken runs things. I need to get to know all of that stuff. I have no preconceived ideas about what I want to do. We’re going to make some assessments as we go, we’ll see how the team’s doing, and then when the time comes to make decisions, I’ll be ready for it.”

A smart manager entering a new organization will always take time to assess and analyze the current state of affairs before making major changes. That appears to be the plan for Jackson with the hockey operations department. Sarah Ryan from Global News asked Jackson about some of the changes he might want to make to the team, and Jackson had this to say:

“I’m not coming in to reinvent the wheel with the team… I hope that I can bring some different views. On the agent side of things, you do a lot of your own player development, you do your own scouting of young kids, we used analytics, I know the Oilers do, like I’m going to look at all of those things, try to be best in class. It won’t happen overnight, but I’m going to dig in all of those things.”

Related: Oilers name Jeff Jackson CEO of Hockey Operations

The words that were sandwiched between “I hope that I can bring some different views” and “try to be best in class” included “player development”, “scouting”, and “analytics”. 

Let’s start with player development. Agents get a percentage of any contract that their players sign, so there’s incentive for agents to ensure that their players are doing what they need to do to improve on and off the ice. That could be getting in the team’s ear about more opportunity, and it could be ensuring that the player is getting proper training and skill work during the offseason. Jackson will have ideas on how players should be developed.

Tyler Wright is currently the Director of Amateur Scouting and Player Personnel. I’ll discuss Wright’s time with the Oilers in more detail in part two of this series, but for now I’ll say that the Player Development department is lacking.

Steve Staios is viewed as a rising young executive in the hockey world. Staios was hired by the Oilers last October as a Special Advisor with a focus on Player Development. Holland talked about Steve Staios’s role with the team in his season ending availability:

“When he came on board [last] year, he did player development because we didn’t really have anybody there and we kind of also didn’t have an Ontario scout. So certainly, we would like to hire an Ontario scout. I think that Steve should do more of the things that an assistant general manager does.”

However, Staios does not appear on the Oilers Hockey Operations staff page anymore. Tom Gazzola reported that Staios has left the organization on The Oil Stream last Thursday:

Oil Stream in 60:

Is Steve Staios done with the Edmonton Oilers?

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— Edmonton Sports Talk (@yegsportstalk) August 17, 2023

Duncan Keith was hired as a Player Personnel Consultant days after Staios joined the Oilers fold last October. Keith’s name does not appear on the Oilers Hockey Operations staff page either. I have no information about Keith’s current status with the organization. Staios’s departure makes me wonder if Keith is still around. Regardless of Keith, there’s a void in the Player Development department that Jackson will have a hand in filling. 

This quote from Holland’s opening remarks about his and Jackson’s discussions surrounding Evan Bouchard and trying to get him some more ice time a couple years ago jumped out at me:

“You were right, we should’ve sped that up.”

Holland said that with a smile and a chuckle, but it speaks to a potential difference of opinion in player development philosophies. Holland is known for being extremely patient with his prospects. Bouchard spent most of the 2021 season practicing but not playing with the Oilers. He had five points in fourteen games that season. He played 81 games the next season and got 43 points. One might argue that Bouchard was deserving of more ice time during that shortened 2021 season, and I suspect that one was Jackson. 

Bouchard was Jackson’s client, so Jackson might have been biased; but his job was to convince Holland that his player was deserving of more opportunity. Perhaps that dynamic will continue into this new working relationship between Jackson and Holland. I wonder if Jackson will push for Holland to shorten his ripening period for prospects. I’ll be quite interested to see how Philip Broberg and Dylan Holloway are handled this year and if it’s indicative of a shift in organizational philosophy on player development. Both are about ready to emerge, but there’s a chance that one or both could end up in Bakersfield to start the year for the extra playing time.

There are some intriguing prospects in the pipeline right now including Raphael Lavoie, Xavier Bourgault, Ty Tullio, Carter Savoie, Matvei Petrov, Jake Chiasson, Markus Niemelainen, and Phil Kemp. Having some of these players become impactful Oilers is essential to success in the McDavid era. We’ll see if Jackson will make any changes that will influence the outcome for these players.

Look out for part two of this series where I’ll focus on Jackson’s potential impact on the Oilers Amateur Scouting department.