August 5, 2024 by Ryan Lotsberg

It’s not often that a team loses their general manager mere days after losing in Game 7 of the Stanley Cup Final, but that’s the exact position the Edmonton Oilers found themselves in this past June. Outgoing Oilers GM Ken Holland has since been replaced by controversial new GM and Executive Vice President of Hockey Operations Stan Bowman.

Bowman finds himself in the enviable position of inheriting a team that came within a goal of the Stanley Cup, and that was bolstered during the first day of free agency. As far as the 2024-25 season is concerned, Bowman has been left with the small but important tasks of re-signing restricted free agents Dylan Holloway and Philip Broberg as well as making the roster cap compliant by opening night. That will be the easy part of Bowman’s task with the Oilers.

Holland built his Oilers team to win during his tenure with the team at the earliest, and in the final year of McDavid’s contract (2025-26) at the latest. Holland only signed three players beyond 2026: Ryan Nugent-Hopkins, Zach Hyman, and Darnell Nurse.

Many fans were frustrated that Holland didn’t swing big at the trade deadline consistently. I would argue that he made trades to add to the team at the trade deadline in all five of his seasons at the helm. Holland traded a draft pick from the 2027 NHL draft to acquire Troy Stecher at the 2024 trade deadline for Pete’s sake. Think about that. His consistent activity at the trade deadline left the team in a situation where they don’t have their full collection of picks until 2028. Combine that with a poor drafting and development record in five seasons, and you’re left with a team whose resources are depleted with zero Stanley Cup wins to show for it.

Related: Oilers Acquire Stecher

The new GM might be in a cushy situation for the 2024-25 season, but the seat will get hot in short order. Bowman’s challenge will not just be to extend the team’s superstars, but to build a winning team around them and the three other players signed beyond 2026 with limited amounts of draft picks and prospects at his disposal.

The only way to do that is to sacrifice players off the current roster. The crux of the problem is that there are “Cup or bust” expectations in Edmonton, and those lofty but entirely realistic expectations will continue to exist as long as McDavid and Draisaitl don the blue and orange. It’s hard to justify subtracting from the current roster to prepare for the future while the team is in “win now” mode. That will have to happen sometime in the next two years though.

Draisaitl’s situation is expected to come to a head this summer, but McDavid still has another year before he can re-sign and two years before his contract expires. Bowman will need to show McDavid concrete evidence of a plan that will keep the team competitive for the entirety of his next contract to ensure that McDavid chooses to re-sign in Edmonton. 

That will involve taking from Peter to pay Paul without upsetting the team’s current status as Stanley Cup contenders. It will take some crafty ingenuity similar to what we saw from Oilers CEO Jeff Jackson in his recent stint as acting GM. Trading Ryan McLeod for top prospect Matthew Savoie because Adam Henrique re-signed is the perfect example of the type of creativity that Bowman will need to show going forward to keep the Oilers competitive as they enter McDavid’s next contract.

Bowman was selected for this role in part because of his three Stanley Cups, but also in part because he has been in a similar situation before. His Chicago Blackhawks had won those three Stanley Cups before Patrick Kane and Jonathan Toews signed their matching eight-year, $84 million contracts that each counted for $10.5 million against a $69 million salary cap. It’s too early to tell for certain, but McDavid and Draisaitl are poised to account for a larger percentage of the salary cap in 2026-27 than Kane and Toews did in 2015-16. Evan Bouchard’s impending large contract won’t help the cap situation any either.

The Blackhawks never made it beyond the first round of the playoffs after Kane and Toews signed those contracts. They lost to the St. Louis Blues in seven games in the first round of the 2016 playoffs. Then they were swept by the Nashville Predators in the first round of the 2017 playoffs. They qualified for the play-in round of the 2020 playoffs staged in the COVID bubble at Rogers Place as the twelfth place team in the Western Conference, and they beat the Oilers in four games. They were dispatched by the Vegas Golden Knights in five games in round one of the 2020 playoffs. That hardly counts as a playoff appearance in my opinion. Aside from 2020, the Blackhawks didn’t make the playoffs after 2017, just two seasons after Kane and Toews signed their mega deals.

Bowman was forced to move Brandon Saad and Patrick Sharp to afford Kane and Toews’ new contracts in the summer of 2015. They had Artemi Panarin waiting in the wings, and he was great for them in his rookie season, stealing the Calder Trophy away from McDavid. The Oilers don’t have a player like Panarin waiting in the wings. Savoie is intriguing, but he will not have finished in a tie for second in KHL scoring before coming to the NHL like Panarin did.

Bowman tried to re-create some magic from 2010 by acquiring Andrew Ladd at the 2016 trade deadline. He also added Christian Ehrhoff at that deadline. The worst move he made at that deadline was trading 2011 second round pick Philip Danault, who has become a high-end defensive centre, for nineteen games of Tomas Flieschmann and fifteen games of Dale Weise. That deadline was really the beginning of the downfall of the Blackhawks. Bowman will need to learn from that mistake and from the situation that Holland being aggressive at the trade deadline every year has left him to handle. It’s like using a credit card. You get something now, but you eventually have to pay it back. Scream all you want about needing to load up at every deadline because the team must “win now”, but a team can’t load up at every deadline and expect to be competitive for a decade or more.

Bowman’s drafting and development record also fell off a cliff after the Blackhawks’ last championship in 2015. Only seven players that Bowman drafted after 2015 have played over or near 100 NHL games, as opposed to the fourteen such players that he drafted between 2010 and 2014. 

Bowman, Oilers Director of Amateur Scouting Rick Pracey, and Oilers Senior Director of Player Development Kalle Larsson will have to be better than Bowman’s Blackhawks team was at drafting and development from 2015-2021 to keep the Oilers competitive into McDavid’s next contract given the Oilers’ limited resources.

Bowman might get a Stanley Cup before his real work as GM of the Oilers really begins, which would unfairly skew the public’s opinion of his work in his favour. I won’t start truly evaluating Bowman’s work until the 2025-26 season because the 2024-25 roster is all but set. That could change if he was to make an impact trade to stabilize the defence group though. 

Related: Oilers name Stan Bowman GM & EVP of Hockey Operations

I still feel that Bowman was the wrong choice for this job not just because of what happened in 2010, but because of how he handled the Blackhawks after Kane and Toews signed those mega deals; but Bowman has a chance to prove me wrong. He has a chance to prove that he has learned from his previous mistakes. I want to be wrong because I want McDavid and Draisaitl to win multiple Stanley Cups as Oilers.