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    Caleb Kerney
    Caleb Kerney
    May 14, 2025, 18:17
    Updated at: May 16, 2025, 22:15
    Jack Campbell (Sergei Belski-Imagn Images)

    EDMONTON – Not everything was sunshine and rainbows.

    The Edmonton Oilers know a thing or two about working through adversity. When Ken Holland first became the Oilers' GM, much work was needed. They were recovering from the mess that Peter Chiarelli created.

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    He did many good things, but he also made some questionable moves. According to Pierre LeBrun, Holland will be announced as the new Los Angeles Kings GM later on Wednesday, with a press conference scheduled for Thursday.

    In honor of Holland being named the Los Angeles Kings’ new GM (although the organization does not officially confirm it at this time), here are the 10 worst moves he made for the Oilers.

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    10- Duncan Keith Trade

    Duncan Keith was a good player for the Oilers during his short tenure. He worked well with Evan Bouchard and helped the youngster acclimate to the NHL. However, not getting the Chicago Blackhawks to retain any salary in the transaction is the only reason to include that deal on this list.

    9 - Kyle Turris Signing & Derick Brassard Trade

    Hey Oilers fans, do you remember Kyle Turris and Derick Brassard playing for the Oilers? Neither do I.

    8- Bouchard Signing

    Evan Bouchard is the future of the Oilers blueline. He has already etched his name in the record books amongst some of the greats, including his own coach, Paul Coffey.

    Holland kicked the can down the road with his handling of the Bouchard extension. Yes, having Bouchard on a short-term deal with an affordable cap hit helps the team today. However, it could cause major problems with that extension set to expire and with Bouchard expecting a handsome raise.

    7) Kostin/Yamamoto For Future Considerations

    Klim Kostin and Kailer Yamamoto are young players who had yet to find their footing with the organization. That being said, surely there was another team in the NHL that could have acquired them by offering draft compensation or the rights to a prospect who was unlikely to sign with them. 

    6) Cody Ceci Signing

    Free agency is the time when teams (typically) overpay for players. One of the biggest overpays in Holland’s tenure with the Oilers was for defender Cody Ceci. Ceci is best suited for a second- or third-pairing role on a Stanley Cup Contending team. $3.25 million for four years was too much money and two years too much for the term.

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    5) Kris Russell Extension

    For the fans of the Oilers who have been around the team long enough to remember Kris Russell – my sympathies go out to you. 

    He was a hard-working player who was forced to play on his off-side too often and was thrown into the deep end because of a lack of depth on defense. They should never have extended him, even if it was only for one-year.

    4) Zack Kassian Extension

    Zack Kassian was a fan favorite player who rebuilt his career (and life) with a trade to the Oilers. That being said, he was offered a big contract extension after a big year where he played a lot with Connor McDavid. This contract became too much for an eventual fourth-line player that the Oilers had to trade several draft picks in order to dump his salary.

    3) Kesselring Trade

    One of the biggest blunders in Holland’s time with the Oilers was trading for Nick Bjugstad. Not only did he not remain with the team once July 1st rolled around, he didn’t do much when he was on the team.

    To add insult to injury, the prospect whom the Oilers traded away (Michael Kesselring) to acquire him was a lineup regular for the Utah Hockey Club this past season.

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    2) Athanasiou Trade

    Andreas Athanasiou was acquired for two second-round picks and Sam Gagner. Trading away Sam Gagner made sense at the time. However, Athanasiou failed to do anything significant while with the team.

    The two second-round picks in the deal ended up being Aatu Raty and Brock Faber. Faber went on to play for the Minnesota Wild, eat up ice time for breakfast (25:11), and be named a Calder Trophy Finalist.

    1) Jack Campbell Signing

    No “worst of” list is complete without at least a mention of the Jack Campbell free agency signing. There were other goalies on the market that Holland could have gone with, yet he decided to pursue the one who was arguably the most inconsistent.

    He was eventually bought out by the Oilers this past summer and hasn’t seen a lick of the NHL since they sent him down early last season. Campbell is a great person and a great teammate. However, five years at $5 million was not the right deal for the Oilers to make.

    Was there any trade or signing that you would have on this list? Let us know in the comments section below.

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