The Edmonton Oilers will formally announce Ken Holland as their seventh general manager in franchise history later this week. They started in 1979/1980 with Larry Gordon (one year), then Glen Sather (20 years), Kevin Lowe (eight years), Steve Tambellini (five years), Craig MacTavish (two years) and Peter Chiarelli (three and a half seasons). Keith Gretzky has held the interim GM tag since January 23rd.

Holland began his career in hockey operations in the summer of 1985 with the Detroit Red Wings as a scout for western Canada. A few years later he was promoted to director of amateur scouting, then he spent three seasons as assistant GM, before getting the GM title on July 18th, 1997.

He has 34 years of experience in scouting and management.

Holland was a major part of the Red Wings drafting that led to their championship teams.

Between 1989-1994 they drafted 18 players who played 500+ NHL regular season games.

In 1989 they drafted Mike Sillinger, Bob Boughner, Nick Lidstrom, Sergei Fedorov, Dallas Drake and Vladimir Konstantinov (Only 446 due to car accident), and Keith Primeau, Vyacheslav Koslov and Jason York in 1990.

In 1991 their first four picks were Martin Lapointe, Jamie Pushor, Chris Osgood and Mike Knuble.
Darren McCarty and Dan McGillis followed in 1992 and they drafted Anders Eriksson in 1993 and Mathieu Dandenault and Tomas Holmstrom in 1994.

The Red Wings signed and traded for some big ticket free agents, but much of their team was built through the draft, and the only first round picks were Sillinger (11th), Primeau (3rd), Lapointe (10th) and Eriksson (22nd).

From 1998-2005 they drafted and developed Pavel Datsyuk, Henrik Zetterberg, Niklas Kronwall, Tomas Kopecky, Jiri Hudler, Tomas Fleischmann, Valtteri Filppula, Jonathon Ericsson, Kyle Quincey, Jimmy Howard, Johan Franzen, Darren Helm and Justin Abdelkader. All of them played 500+ games and only Kronwall (29th in 2000) was a first round pick.

Since their last Stanley Cup victory in 2008, the Red Wings have still managed to draft and develop well. But it is very difficult to continually find Hall of Fame players in the later rounds.

The drafting and developing of later picks like Lidstrom, Federov, Datsyuk and Zetterberg created a solid foundation for three decades.

Expecting to maintain that level of excellence in scouting and developing is unrealistic. I don’t believe it means Holland and his staff in Detroit lost their touch over the past decade. They still made some solid picks, but when you lose Hall of Fame talent it is very difficult to replace it. They were able to replace Steve Yzerman and Federov with Datsyuk and Zetterberg, but when the latter two and Lidstrom retired the drop in talent was apparent.

The Wings have some solid young players, and some believe they are now on the track back up towards becoming a contender. Holland won’t be around to guide them, as he handed the GM title to Yzerman and now Holland will come to Edmonton.

Holland helps build the Red Wings Championship teams and then he continued to keep them at the top for two decades.

He inherits an Edmonton organization as the opposite end of the NHL spectrum.

The Oilers are the worst franchise in the NHL under Daryl Katz. They have the most losses, and fewest wins, since Katz purchased the team in the summer of 2008. Since his arrival as owner, the Oilers have a losing culture, both on and off the ice.

Some cringe at the term culture, mainly because there is no exact formula to define it, but losing is synonymous with the Oilers for over a decade and Bob Nicholson hired Holland hoping he can reverse what seems like an unbeatable and never-ending trend.

Holland has a major challenge in front of him, much different than when he took over the Red Wings, but also different than when Peter Chiarelli was hired in April 2015.

I’ve read a lot of people comparing Holland to Chiarelli. Yes, both had experience, had won Cups with their previous team, but had some struggles near the end of their tenures, but from my seat the comparisons end there.

They are different people, with different personalities. I can only speak about my interactions with both men. I’ve spoken to Holland numerous times over the past 18 years and he was always open and inviting. Chiarelli not as much, other than a lengthy conversation we had once at a golf clubhouse. I’m not saying one approach is better, just outlining I noticed a major difference in how they interacted with me when they GM teams outside of Edmonton, and then in the time Chiarelli was here.

The other fact is the difference in the talent pool of the Oilers organization in 2015 compared to now.

When Chiarelli came to Edmonton he had no organizational depth, but he had a lot of top-end skill. Sadly, for Oilers fans, he gutted the skill with some horrific trades that saw him trade away a first, a second, Taylor Hall and Jordan Eberle for Griffin Reinhart, Adam Larsson and Ryan Strome. He added to that with more downgrading of skill when he moved Strome and Drake Caggiula for Ryan Spooner and Brandon Manning. However, during his tenure, the Oilers have created a pipeline of solid prospects in Evan Bouchard, Caleb Jones, Ethan Bear, Tyler Benson, Cooper Marody, Kailer Yamamoto, Dmitri Samorukov, Kirill Maksimov, Filip Berglund and Ryan McLeod. They also signed Joel Persson. (William Lagesson was drafted prior to Chiarelli’s arrival).

On June 20th, six days before the 2015 draft, Chiarelli fired Stu MacGregor and three other amateur scouts. They’d done their scouting reports, but he wanted to move forward in a different direction. It was the right move, excluding the Reinhart trade, and the Oilers drafting in the 2nd round and on has improved recently. At least to the point where they have prospects who look like they could help the NHL team in a season or two.

Holland inherits an organization which should see some roster spots filled internally from drafted players during the next few seasons. But he doesn’t have as much NHL top-end depth that the Oilers had in the summer of 2015.

Luckily for him, he gets to shape his team around Connor McDavid and Leon Draisaitl. He has some other high-end pieces in Ryan Nugent-Hopkins, Darnell Nurse and Oscar Klefbom. The cupboard isn’t completely bare, but he needs to fill in the gaps on the roster, and use his 22 years of GMing experience to find ways to shed one or two of the big contracts.

Of course Holland’s GM resume has a few contracts that didn’t work out. Overpaying in free agency rarely works. Frans Nielson hasn’t been as productive as they’d like. He signed veterans Danny Dekeyser, Justin Abdelkader and Darren Helm to over-priced contracts. I believe the toughest challenge for any GM is to avoid the emotional-home-grown re-signings. I’m not naive enough to see why teams sign veterans, and players epitomize what an organization wants. Good people, who play hard, but rewarding them for past success can be dangerous.

The thing is if you let them walk, you need someone internally ready to replace them, otherwise you overpay on a player you don’t really know, and I understand why GMs will stick with the person they know.

It is a fair critique of Holland to say some of his recent re-signings of veterans in Detroit haven’t worked out, but that doesn’t mean he will do that here. He has no deep emotional connection to any Oilers players. He hasn’t drafted them, developed them, got to know their family, wife and children.

I see more positives than negatives on Holland’s resume. But there are some key questions that need answers.

I strongly believe Bob Nicholson should have made some of those changes prior to hiring a new GM. I don’t think it should be the new GM’s responsibility to remove people he has never worked with. Nicholson should know who didn’t excel in their job the past four seasons. It wasn’t only Chiarelli.

Regardless, Holland will make some more changes. I expect them to be in pro scouting and management, more than on the amateur scouting side. I could see him keeping Keith Gretzky, and I could Gretzky accepting a spot under Holland much easier than if a rookie GM came in.

So ultimately, which other changes are coming? It can’t remain status quo. Chiarelli’s only move within upper management was bringing in Gretzky, and he arrived in August of 2016, after the Reinhart and Hall trades.

All the other people remain the same from prior to Chiarelli’s hire and after his firing. It is irresponsible and misleading to think he was the only one who erred in player evaluation.

Bob Nicholson reported that Pat Verbeek will join Steve Yzerman in Detroit as assistant GM. So will Holland bring anyone from Detroit with him? Ryan Martin (Assistant GM), Kris Draper (Assistant to the GM) and Shawn Horcoff (Director of Player Development) are currently in Detroit. (Does the fact Draper has a Dwight Schrute-like title make anyone else chuckle or only me?)

The Oilers lack of an experienced and professional analytics group needs to be fixed immediately.

The organizations approach to developing players. It improved under Chiarelli, but still not enough. Their rushing of Jesse Puljujarvi, when he clearly wasn’t NHL ready was wrong. Same with Kailer Yamamoto. Holland has always been patient with players, and he wisely had Filip Zadina, 6th pick in 2018, in the AHL this season, not floundering in the NHL. I expect he will maintain his patient approach with prospects.

I expect a new head coach, but do they have to change the entire staff? Wouldn’t it be prudent to keep one or two of them around? Do they really need another new defence coach? That would be the third new defence coach in three seasons. Not ideal. I’ve been told by many players they liked the assistant coaches and they expressed this to Nicholson in their exit interviews.

It isn’t as much about learning a new system, because let’s be honest there aren’t that many systems in the NHL. The players have been exposed to them already. It is more about communication and understanding a player’s personality, emotions and what they do best. Put them in the best position to succeed. Connecting with them is arguably more important than the system you want them to play.

I completely understand why Dave Tippett, or any other coach, would want to hire at least one assistant coach. I get that, and I fully expect him to bring in at least one coach, maybe two. But I see benefits in keeping one of two of the existing staff. Glen Gulutzan, Trent Yawney and Manny Viveiros have only been around one year. They haven’t been around five plus seasons, and I don’t see them in the same situation as the management team.

Holland is a different GM than Chiarelli, but if the organization wants Holland to have more success then they must be willing to make more changes within the current management structure.