From Ken Holland’s perspective, you could see why he’d up and leave from Detroit to take on the roles of president of hockey operations and general manager with the Edmonton Oilers. 

The 63-year-old, who recently switched from his decades-long role as Detroit Red Wings GM to a senior vice president position with the franchise after Steve Yzerman returned, is taking a reported five-year, $25 million dollar deal to try and turn around the Oilers with Connor McDavid as the centerpiece. Enticing for any one, clearly, especially when given, per the official release, “full autonomy.”

But if you’re Oilers CEO Bob Nicholson and your goal is to make a rebuild into a quick transition back into a playoff team, is Holland the right choice? He has four Stanley Cups on his resume while running the Red Wings, sure. But once the franchise’s golden generation reached their golden years in the NHL, that success came to an end, and there were no younger reinforcements coming through the Red Wings’ system to sustain those years of winning, at least not immediately.

One of the things Holland was known for during his time in Detroit was allowing prospects to develop properly in the AHL, even if some thought those players were well-beyond ready for the NHL. 

Three of the Red Wings’ top five scorers this past season probably could have been up earlier in the NHL considering the franchise was and remains in a transition phase after the end of their 25-season playoff streak. Andreas Athanasiou spent parts of three seasons in the AHL before becoming a full-time NHLer. Anthony Mantha needed extra time to find the scoring touch that served him well in junior and has posted back-to-back 20-goal seasons. Tyler Bertuzzi broke out this past season with 21 goals after finding his way through 137 games in Grand Rapids. 

Jesse Puljujarvi had a roller coaster of a 2018-19 season. Kailer Yamamoto got in 17 games with the Oilers. Caleb Jones and Cooper Marody have accumulated good experience with the Bakersfield Condors. Evan Bouchard is coming soon. Those are the prospects the Oilers need to get right if they’re going to have any impact at the NHL level. Letting them overripe in the AHL would serve them well as opposed to yo-yo’ing them between levels, messing with their development.

But while prospect development could be looked at as a positive, some of the contracts Holland has handed out has ended up handcuffing him while attempting to maintain their status as a playoff team. Justin Abdelkader, Frans Nielsen, Darren Helm, Trevor Daley, and Jonathan Ericcson are some of the term-heavy, cap-eating deals that have helped put the Red Wings in the position they currently reside.

That track record can be improved if Holland surrounds himself with smart people. Pat Verbeek, who was a pro scout with the Red Wings under Holland, is leaving his role as assistant GM in Tampa to return to Detroit in the same position under Yzerman. But will the same be said for Tyler Wright, who currently works as the Red Wings’ director of amateur scouting?

The staff will need to be a strong and creative one considering the Oilers’ current position under the salary cap and some of the roadblocks that remain in place as they try to build a team around McDavid and Leon Draisaitl.

Then you have the question of the head coach now that Ken Hitchcock will not be back and possibly moving into an advisor role. Dave Tippett seems itching to return behind a bench and doesn’t want to wait for Seattle’s NHL entry. Dan Bylsma was an assistant in Detroit this past season. Jay Woodcroft has done a great job in his first season with the Oilers’ AHL affiliate in Bakersfield.

There will be plenty of options available to replace Hitchcock.

Nicholson and Oilers owner Daryl Katz feel Holland is ready for a successful second act as an NHL GM. They are, of course, also desperate to ensure time isn’t wasted while McDavid is still posting 100-point seasons. There’s plenty of work ahead for Holland to make that a reality, and this move cannot fail and set the franchise back any longer.

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Sean Leahy is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @Sean_Leahy.