The Edmonton Oilers hired Ken Holland on May 7th, 2019. The Oilers finished 23rd in the NHL in 2018 with 78 points and followed that up with a 25th place finish in 2019 with 79 points. Over two years they were 25th in total points with 157. Holland inherited two great players in Connor McDavid and Leon Draisaitl, but he inherited a bad hockey team.

Since arriving Holland made many moves to support his two superstars and during his four seasons the Oilers amassed the 8th most points and third most regulation wins. They’ve played the 9th most playoff games and Holland has built the Oilers into a legitimate Stanley Cup contender.

He has made significantly more good moves than bad. He’s always been honest that every move won’t work, but it seems foolish to suggest Zack Kassian’s four-year, $3.2m AAV deal overshadows the Zach Hyman signing. Kassian’s signing didn’t work out, but Hyman’s has. You can go across the board and there are more positive signings/trades than bad ones.

The most impressive aspect, for me, has been Holland’s rebuilding of the blueline despite two significant losses that were out of his control. Oscar Klefbom played in Holland’s first season as GM in 2020, but a career-ending shoulder injury forced Holland to find a replacement. The following off-season, Adam Larsson opted to leave in free agency. The main reason was that his mother didn’t want to return to Edmonton where her husband suddenly died a few years earlier. The organization gave Larsson all the time he needed to make a decision, and he ultimately felt a new city would be best for him and his family.

Losing two of this top-three defenders in less than 10 months was a big blow, but Holland navigated it quite well. He brought in Tyson Barrie as a UFA and Barrie played very well for the Oilers, especially during the playoffs. He eventually moved Barrie to Nashville for Mattias Ekholm. He replaced Larsson with Cody Ceci. Ceci was excellent in his first season in 2022 but had a tough 2023. Holland acquired Brett Kulak for a 2nd rounder and Kulak has been a very solid addition with a good cap hit.

McDavid, Draisaitl and Ryan Nugent-Hopkins are the only forwards who remain from the 2019 team. The remaining forwards from that season included Milan Lucic (79GP), Zack Kassian (79 GP), Alex Chiasson (73), Kyle Brodziak (70), Tobias Rieder (67), Jujhar Khaira (60), Ty Rattie (50), Jesse Puljujarvi (46), Colby Cave (33), Drake Caggiula (29), Sam Gagner (25), Josh Currie (21), Kailer Yamamoto (17), Brad Malone (16), Joseph Gambardella (15).

With a variety of trades and signings Holland has now constructed a forward group to support his top players by adding Zach Hyman, Evander Kane, Connor Brown, Warren Foegele, Dylan Holloway, Mattias Janmark, Derek Ryan and Raphael Lavoie. Ryan McLeod was already drafted when Holland arrived. We’ll find out this October if Lavoie is ready to compete for an NHL job, and Holland still needs to find a 4th line centre to push Lane Pederson.

I don’t think the 2023 roster is complete, and I expect Holland will make more moves leading up to the trade deadline.

Holland has added some much-needed stability to the organization. The dysfunction is gone. Holland treats everyone in the organization with respect. He is demanding without being a prick. The Oilers have improved every year since he arrived.

They were 12th in points % 2020 when the season was shut down unexpectedly due to COVID.
They finished 11th in 2021 but lost in the first round to Winnipeg.
They were 11th in 2022 and made it to the Conference Final.
They finished 6th last season before losing to Vegas in the second round.

The players have learned some valuable lessons the previous few postseasons, especially this past May when they lost to Vegas. They were good enough to win, but self-inflicted errors cost them. Holland’s decisions have put the Oilers in a position to compete for the Stanley Cup for the next few seasons at least.

Since he replaced Dave Tippett with Jay Woodcroft on February 10th, 2022, the Oilers have the second most points and second most wins in the NHL, trailing only the Boston Bruins.

Holland hasn’t been perfect, but no GM, or human for that matter, is. He has made more good moves than bad, and as he enters the final year of his five-year contract, I keep hearing whispers this might be his final season in the NHL as GM. If it is, Holland has left the Oilers in a much better position than they were in when he arrived. His successor will inherit a much better team than Holland did in May of 2019, regardless of if Holland opts to leave at the end of this season or the year after.

Up to this point Holland has done a very good job. This season, specifically leading up to the trade deadline, might be his defining moment as GM of the Oilers. The unpredictability of injuries at inopportune times can impact any team, coach or GM, but thus far Holland has done a solid job of navigating through injuries, COVID, and a season with no fans in the stands to make the Oilers a contender.

Will he make one franchise-altering move to push the Oilers closer to a Stanley Cup this season? His core is in place, so I’m not sure he has to make a major move, but as we near the trade deadline the areas of need will be clear. The Oilers should be a Cup contender this season, and whether they win this season or in the next two or three, Holland’s fingerprints will be all over that championship whether he is sitting in the GM chair or not when the Cup is lifted.

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