Photo: Carlos Osorio (AP)

Ironically, the Edmonton Oilers’ signing of Ken Holland as their new GM has all the hallmarks of Holland’s recent moves in Detroit. You know, the ones that made Red Wings fans so excited to see Steve Yzerman arrive back home last month. Edmonton giving so much money—a reported $25 million over the next five years—to a big name whose best years are behind him puts Holland in a category with current Red Wings signings like Frans Nielsen or Justin Abdelkader—each symptoms of Holland’s over-reliance on veterans and his unbreakable loyalty toward former winners.

Holland is a weird study, with missteps in recent years that have retroactively stripped him of the credit for three Stanley Cups as the GM for the Red Wings from 1997 to 2019 (four Cups with the organization, total). Detroit was thrilled to see him politely move along for Yzerman because, as the salary cap took hold of the league, Holland could never seem to make the belt-tightening, unsentimental decisions that look towards the future instead of preserving the past. Since the team made so many shortsighted moves to tack a few first-round exits onto the end of its impressive playoff appearance streak, the Red Wings have been stuck near the bottom of the standings for the past three seasons.

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But the Oilers couldn’t afford to be too choosy in their hiring of a new GM, because Peter Chiarelli did a real number on this franchise, and that $25 million Holland’s getting reflects just how difficult and unappealing this job is going to be. What a ridiculous thing to say about a team with Connor McDavid and Leon Draisaitl, but it’s true. The Oilers are hamstrung by ill-advised long-term deals with essentially useless players like Milan Lucic, Andrej Sekera, and Kris Russell, which means Holland probably won’t be able to make any splashy signings for a couple of years.

The most drastic thing Holland could do in his first weeks on the job is deal Edmonton’s first-round pick (eighth overall) for someone who can help them win now (a defenseman, specifically). But more likely, a good chunk of Holland’s job over the next couple of years should entail crossing his fingers and hoping prospects like Evan Bouchard, Kailer Yamamoto, and Jesse Puljujärvi pan out. Even in a best-case scenario, the Oilers will have to win as a lopsided team dominated by its top two centermen, because all the help is coming from within.

For this marriage to work, owner Daryl Katz and Oilers fans will need to trust that Holland can make the small but meaningful choices that would slowly but surely pull this franchise out of its self-made disaster. But perhaps more importantly, Holland needs to show that he can be smart with his assets when he doesn’t inherit a team already set up for success. Do that, and it would shut up his doubters who love to praise Jim Nill and Håkan Andersson for earning all those trophies in Detroit. In Edmonton, Holland won’t have money, and he won’t have all those magical ’90s draft picks that sustained over a decade of winning. If he wants to prove he can win without the massive budget to bring in several future Hall of Famers, he’s come to the right place.