Edmonton Oilers, Ken Holland

Oilers: Signs Point to 2023-24 Being Holland’s Last Season As GM

In one of the most pivotal scenes in the movie “Silver Linings Playbook,” Jennifer Lawrence’s character revealed, “If it’s me reading the signs,” which showed exactly where she stood. It almost seems as if the Edmonton Oilers have taken a page out of “Silver Linings Playbook” because there are more and more signs indicating that this could be Ken Holland’s final season as general manager in Edmonton.

The Most Obvious Signs

This one almost goes without saying; Holland is in the fifth and final year of his five-year contract with the Oilers. So much of his future, and many others in the organization, depends on the success of the franchise in 2023-24. It’s Stanley Cup or bust for Connor McDavid, Leon Draisaitl and the team this season.

Edmonton Oilers general manager Ken Holland
Edmonton Oilers general manager Ken Holland (THE CANADIAN PRESS/Jason Franson)

Holland will be turning 69 years old on Nov. 10, and that’s getting up there for an NHL general manager these days. Although Holland seems like he is in fine shape, you have to know that he doesn’t have anything to prove as he is already a member of the NHL Hall of Fame having won four Stanley Cup championships with the Detroit Red Wings during his tenure with the team.

Another Big Sign Was the Oilers Naming Rick Pracey Director of Amateur Scouting

The move to bring in Pracey and replace Tyler Wright has new CEO of Hockey Operations Jeff Jackson’s fingerprints all over it. Wright came over to Edmonton with Holland from Detroit in 2019, and based on how loyal and patient Holland has been over his career with players, coaches and management, you get a sense that relieving Wright of his duties was not an easy decision for Jackson, Holland and the Oilers.

Winning A Stanley Cup in 2024 Could Be Holland’s Swan Song

During this past off-season, Oilers players and management have mentioned numerous times how the team is “all-in to win” in 2023-24. This included Holland, who you have to know would dearly love to win one more Stanley Cup championship.

Related: Ken Holland’s 4 Biggest Decisions as Oilers GM

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If Holland were to win one more, his legacy would clearly be cemented as one of the best general managers of all time in the NHL, joining the likes of Sam Pollock with the Montreal Canadiens, Bill Torrey of the New York Islanders, Glen Sather of the Oilers and Lou Lamoriello when he was with the New Jersey Devils. Holland already ranks high on this list, but winning one more Stanley Cup in Edmonton would take him to a whole new level.

The Oilers Feel Like They’re More Jeff Jackson’s Team Now

When Jackson was hired as CEO of the Oilers on Aug. 3, there was a sense that changes were afoot. However, the recent signing of Pracey as Director of Amateur Scouting came quickly, just 16 days after Jackson was hired. That indicates that Jackson is definitely in charge of the future of the Oilers. As the 2023-24 NHL season progresses, there is sure to be more signs of change within the Oilers’ organization. It’ll be interesting to watch especially when it comes to Holland.

Edmonton Oilers Wayne Gretzky Philip Broberg Ken Holland
Edmonton Oilers Wayne Gretzky, Philip Broberg and Ken Holland (THE CANADIAN PRESS/Jonathan Hayward)

Right now, he and the Oilers are holding their cards close to their chest, but a succession plan surely must have been talked about. If Holland does indeed retire from his general manager duties after this season, you have to wonder if Brad Holland or Keith Gretzky will get their opportunity to take over as general manager. Or does Jackson have someone else in mind? Whatever the case, the signs are pointing to more change in the front office for the Edmonton Oilers.

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