Lowetide: What Oilers’ Jeff Jackson hire could mean for front-office’s future

The Edmonton Oilers shattered a sleepy summer’s morning on Thursday with the hiring of Jeff Jackson as the team’s new CEO of hockey operations.

Fans who like a punchy headline framed it as “the Oilers hired Connor McDavid’s agent to run the show” but this hire has many levels.

The release also informs that Paul Coffey, who has been working as a special adviser, will aide Jackson in his role.

There is mention of Jackson working closely with Ken Holland, who is in the final season of his five-year deal as general manager. Holland will report to Jackson, as will Coffey, according to the release.

There will be much speculation in the months to come in regard to the next general manager, should Holland step back. That hire (or a new contract for Holland) will be one of the first major moves of the Jackson administration.

Jackson’s background runs all of the NHL’s landscape, from player to AGM with the Toronto Maple Leafs to a prominent NHL agent — his biggest client was McDavid. His reputation is immaculate based on the early reaction to the hire.

Scouting

Oilers fans should expect some quick movement from the new hockey operations CEO. What does that look like?

Any changes in scouting, pro or amateur, would have to be addressed immediately. As an example, Ken Holland arrived in the spring of 2019 and hired Tyler Wright (amateur) and Archie Henderson (pro) in July, after the draft and before the Hlinka-Gretzky tournament. Hlinka-Gretzky signals the beginning of the new amateur scouting season.

If Jackson is planning a change in this area, it’s likely to occur soon.

The next window of opportunity would be after the draft lists are put to bed for the 2024 selection.

General manager

Jackson inherits several possible succession plans as he arrives in Edmonton. Here’s a quick look at the in-house candidates.

• Keith Gretzky is one of the Oilers’ assistant general managers and GM of the AHL Bakersfield Condors. His most famous contribution to the NHL team is helping in the development of prospects at the AHL level, but he was interim general manager when Edmonton dealt Ryan Spooner for Jackson client Sam Gagner in February 2019.
• Bill Scott is another AGM and the team’s capologist (his official title is director of salary cap management) and former AHL general manager. He is best known for discovering centre Mark Arcobello, who went from undrafted free agent to NHL player.
• Brad Holland has helped improve pro scouting and is considered a rising star in the organization. It’s unknown if he would be considered for the general manager’s role but he possesses a strong resume and has done well in his brief time with the Oilers.
• Steve Staios is the latest arrival and was considered the odds-on favourite to replace the elder Holland not long ago. However, an ownership change in Ottawa has the Senators rumoured as Staios’ landing spot as the GM.

What we know today is this: If any of these men were going to be taking over before the start of the 2023-24 season in the GM role, it’s likely that announcement would have been made as part of the media avail by the team. Any of these names could emerge, but Jackson will have time to evaluate.

The favourite 

It goes without saying Jackson himself may slide into the GM’s chair at some point. His knowledge of the league, of player negotiations and of the other 31 general managers would give him an edge.

The Coffey announcement dovetails with Jackson taking on both roles.

One important item: McDavid’s influence on the Oilers’ front office and in personnel decisions was massive before today. The hiring of his longtime agent will only serve to increase that influence in the years to come.

Long-term applications

A former agent like Jackson will have knowledge of free-agent opportunities because he is just now removed from being on the other side of negotiations.

That can be a massive advantage for an NHL team, and may happen at this year’s trade deadline. Fresh knowledge of a rental player’s willingness to re-sign with Edmonton could be advantageous both for the 2024 postseason and beyond.

For fans, the relationship between Jackson and McDavid is brilliant news. If this signing secures a third McDavid contract and keeps Leon Draisaitl in Edmonton for another long-term deal, Oilers fans will view the addition of Jackson as a home run.

Bob Nicholson

The team website gave a hint about the Thursday announcement recently. A slight alteration of Bob Nicholson’s bio reads, “from 2019 to June 2023, Bob held the role of Chairman, Edmonton Oilers Hockey Club, devoting his energies to OEG’s hockey franchises and growing sports businesses.”

The job being in the past tense, it became clear Nicholson was stepping back from his previous heavy involvement in the team’s day-to-day operations.

As is the case with much of the news, it isn’t completely clear what role Nicholson will play moving forward. It is likely to be less public.

Analytics

One of the difficulties in proving that management is making progress in the important area of analytics comes in giving credit for successes.

As an example, the Zach Hyman signing was supported by the numbers and the eye test. So, which is it?

The answer comes in having someone in upper management who both understands and values what analytics brings to a team.

When the Oilers employed Tyler Dellow (now senior vice president of hockey strategy and analytics with the New Jersey Devils) it was possible to identify areas that needed to be addressed, and obvious analytics solutions, but the follow-through wasn’t there.

The Oilers under Peter Chiarelli were not giving enough value to what the numbers were saying. The only transaction during that period that was both out of character for the organization and a strong analytics solution was the signing of Andrej Sekera.

Trading Taylor Hall, signing Milan Lucic and other moves ran counter to optimizing value. The advanced numbers can help teams predict erosion due to age, fair compensation for free agents, and the difference in real value between an outscoring winger and a shutdown defenceman.

Jackson will be comfortable making big decisions using both the eye test and the math of hockey. He will also know what elite teams in the NHL value most.

Fans will be able to see quickly what kind of analytics team the new CEO envisions. Although rosters are set on and off the ice for 2023-24, there are dozens of excellent options in the public market that would be available right now to a team like the Oilers.

Edmonton needs help in finding people to crunch numbers, find the truth in them and then communicate those important pieces of information in a timely way. Perhaps a team could work together and proactively produce a proposal to acquire a player that management hadn’t contemplated.

It’s uncertain whether any general manager in Edmonton’s employ has enjoyed that kind of advantage, but Carolina Hurricanes general manager Don Waddell has that on call every day of the year.

Bottom line

Oilers fans, struck by the news, are contemplating the changed world that Jackson will create.

Jackson himself will need to focus on what can and should be done before training camp and then before the deadline.

There are so many options for the new CEO it might be similar to ordering a meal from a 30-page menu.

One of the first items on the agenda, after signing the team’s remaining RFA (Evan Bouchard), is deciding if a transaction is necessary in order to have room to wheel under the salary cap during the 2023-24 season.

Holland is running it right up to the cap, pressure brought on by miles and miles of free-agent signings, buyouts and trades made to shed dollars.

Jackson will also need to decide on what to do about a thin group of prospects bubbling under at this time.

For now, the news is out and Oilers fans have fresh ideas and arguments to make.

The first big move, if there’s going to be a change, will come at the general manager level or in scouting.

New general managers mean change. The Oilers will be no different than any NHL team. Expect movement with the new CEO bringing in his people.

One question remains unanswered: Did the Oilers ask Ken Holland to step back a la Nicholson? That might have been the play here.

Finally, the only conclusion that can be drawn from this announcement has owner Daryl Katz increasing his chances of signing his most important asset — McDavid — by hiring the individual closest to him professionally.

At first blush, it’s hard to find anything negative in this hire.

If the Oilers win the Stanley Cup in the next few seasons, this week will be remembered fondly.