When Ken Holland was hired as general Manager, the Edmonton Oilers had made the playoffs once in the previous 13 seasons. Even the addition of Connor McDavid didn’t lead to instant success. They did make the playoffs in McDavid’s second season but then finished 23rd and 25th in 2018 and 2019. Holland was hired in May of 2019 to try and make the Edmonton Oilers a playoff team and hopefully a Stanley Cup contender.

During his five-year tenure, the Oilers have played the seventh-most playoff games. Their path to the 2024 Stanley Cup Final was anything but smooth, and despite two major setbacks within a 10-month span, Holland has been able to surround his two superstar forwards, McDavid and Leon Draisaitl, with a support group that is four wins away from hoisting the Stanley Cup.

This was the roster Holland inherited in May of 2019.

Draisaitl – McDavid – Kassian
Lucic – RNH – Chiasson
Puljujarvi – Gagner – Reider
Khaira – Brodziak – Caggiula
Malone – Cave – Rattie

Klefbom – Larsson
Nurse – Russell
Sekera – Benning
Gravel

Koskinen

Only McDavid, Nurse, Ryan Nugent-Hopkins and Darnell Nurse remain from that team. They Oilers had draft picks Vincent Desharnais (2016), Stuart Skinner and Ryan McLeod (2017) and Evan Bouchard (2018) in the system, but none were playing pro when Holland arrived.

He did a major reconstruction of the roster, and the biggest challenge was losing Oscar Klefbom and Adam Larsson in a span of 10 months. Not many teams can remain competitive while losing two of their top-three defenders for reasons outside of the organization’s control.

Holland’s first year also included the pandemic. It wasn’t a typical transition to a new club, but despite the challenges, Holland has had made more good decisions than bad, and a few key ones have led to the Oilers to the Stanley Cup Final.

I spoke with Holland about his time in Edmonton and how they got to this point.

Ken Holland: They’d finished 25th and 23rd the previous two seasons, but I knew that we had an engine, a group of people who could drive your team. I think I said at the press conference, I was hoping that year one, it’s hard to say you’re going to make the playoffs after finishing 25th, but I thought that we needed to be in the playoff hunt and make progress and challenge to make the playoffs.

The big curveball, obviously, was after year one when I knew that (Oscar) Klefbom’s career was over and that Adam (Larsson) was leaving. You’re losing half of your top four, so that certainly was a massive setback. When I took over, the hope was that within two, three years you could be competitive, you could get into the game.

I’ve been at this a long time. It’s hard to get into that area in the standings. It’s easier to go from 25th to 11th, 12th, or 13th than it is to go from 11th, 12th or 13th to the top six or eight teams. Those are the teams who are established. They’ve got a culture. They do it year after year.

That’s what we’re all trying to build. But certainly, I knew that with Connor, with Leon, with Nuge, with Nurse, with Klefbom, with Larsson, I felt that this team had a nucleus of players. We obviously had to build around it. However, when you lose two of your top three defensemen in a span of 10 months, Klefbom’s career was over due to shoulder surgery and for personal reasons, Larsson didn’t want to play in Edmonton (his father passed away unexpectedly while visiting in Edmonton, and Larsson’s mother couldn’t come back to Edmonton; it was too hard for her).

That’s why I went out and signed Cody Ceci, and then acquired Duncan Keith. I wanted the veteran leadership on the backend to try and keep your team going in the right direction while trying to develop Evan Bouchard, Vincent Desharnais, Philip Kemp and Ethan Bear. Bear made the team the first year, but you’ve got to try to be competitive while you’re behind the scenes, you’re drafting and developing. Also, we were capped out the first year I got there, so I couldn’t make any major salary cap additions.

Then obviously, the pandemic hit and the salary cap barely moved for five years, so that certainly was another challenge for all the teams in this league.

Holland: Probably after year one when we went through our analytics. We were more of a rush team. I think if you want to win in the playoffs, you need to be a cycle team. You want to score off the rush, but you have to be able to cycle the puck. So that was a big focus moving forward.

In the summer of 2021 two of the top-five forwards in the National Hockey League, in terms of cycling and forechecking, were (Warren) Foegele and (Zach) Hyman. I talked to Don Waddell, who was my assistant manager in 1998 in Detroit, and we had a good relationship. He was looking for a defenseman. We wanted to bring in some forwards who were going to forecheck and hang on to pucks down low. So, we got Foegele for Bear.

I would say to you, you start out with a plan, but along the way, you need some luck. You need some things to fall your way. Certainly, we were fortunate that Zach Hyman, who could have chosen to go any one of a number of spots, elected to come to Edmonton. That’s good fortune. Certainly, having Connor McDavid and Leon Draisaitl on the team I’ve got to believe played a big factor in Hyman making the decision to sign with us, but you still need him to make that decision.

We also made the decision to trade Milan Lucic for James Neal a year earlier. As it turns out, in hindsight, we had the ability to buy out Neal, which we couldn’t have done with Lucic, and that freed up $3.5 million, which we put towards the Hyman deal.

You have these plans, but then you need some things to fall your way. When we added Hyman and Foegele, who we thought both were top nine forwards, that was when I thought we were making progress and going in the right direction.

Holland: I guess, from my perspective, fortunately, I was on teams that were in the playoffs, and then into the final eight, the final four, and I certainly understand the importance of depth. And I’m not the only one. Some people understand it, but you’ve got to find it.

If you look back to the first year I came in here, we signed a whole lot of players for cheap, as you hope a few can contribute. We signed Josh Archibald, Riley Sheehan, Tomas Jurco, Gaetan Haas from Switzerland, Joakim Nygaard from Sweden. We signed a whole lot of players hoping a few could contribute.

After that year, some of them were gone, and we kept Archibald, but then he didn’t want to get vaccinated. So, he was gone too. You are trying to find players who can contribute in limited minutes. Maybe score 10 goals, be good on the penalty kill and sound defensively.

We drafted Mattias Janmark in the third round many years ago in Detroit. I kind of followed Janmark’s career, and when he became a free agent in the summer of 2022 we offered him a contract. And then, due to our cap crunch, we ended up putting him in the American League until Evander Kane had the wrist injury, and Janmark came up from the minors.

Getting depth is important and you just keep working at it, and Jason, some work out and some don’t. You want more hits than misses. Klim Kostin, we had just acquired a month before Evander Kane went down, and he and Janmark come up. They played with us all year. We tried to re-sign Kostin, but at the end of the day, we were really negotiating against the KHL.

We ended up trading him to Detroit, and we traded Kailer Yamamoto with him, because again, we were trying to create cap space. Kostin loved it here, he loved his role, loved the team, and wanted to be here. But we couldn’t match what the KHL offered, so moving him and freeing up Yamamoto’s cap space gave us a bit of cap flexibility.

With depth players you’re trying to find players who fit, but they’ve got to understand their role and they’ve got to fit the role and they’ve got to want to be on that team. Fortunately with guys like Janmark, he’s accepted it, same with Derek Ryan and Connor Brown and in January we signed Corey Perry.

Going into the deadline this year, we felt we needed more depth up front, guys who could play center, win draws, kill penalties, chip in, and we made the deal with Anaheim to acquire Adam Henrique and Sam Carrick. In a span of six weeks, leading up to the deadline we added three players who have specific skills and assets we felt we needed.

Perry shoots right, plays right wing, Henrique shoots left, can play left wing, can play center, can penalty kill. Sam Carrick shoots right, can play centre or wing, can win faceoffs and is physical. You need lots of players with versatility, and heading into the deadline that was what we hoped to add.

We also wanted to get one more defenceman, but we knew we had Broberg playing well in the American Hockey League. He was in a great place. He was playing 25 minutes a night — why call him up to be a seventh defenseman, and play limited minutes? He was the number one defenceman in the AHL, so we opted to keep him there and acquired Troy Stetcher. Unfortunately, Stetcher’s season is over because of a cyst in his ankle but allowing Dylan Holloway and Broberg to spend time in the American League down the stretch really helped us, and them.

At the deadline we had to send Holloway down for two reasons: one, we had to create some cap space and two, we had to get him playing. Scoring 10 goals in 18 American League games, he got his confidence back. He also worked on his play away from the puck and he’s been a big contributor in the playoffs because of his time in the AHL.

But with depth players, you never know truly know how it’s going to work, but they’ve all contributed, and really, it’s a credit to Kris Knoblauch. The job he’s done managing the roster and making the decisions down the stretch in the regular season and in the playoffs. He’s pushed all the right buttons… Perry is in, Perry’s out, Carrick is in, Carrick’s out, Ryan is in, Ryan’s out, as well as Foegele, McLeod, Broberg and Desharnais. We lost Henrique with an injury for a bit, but our depth has really been a big piece of the puzzle.

Holland: Obviously we are excited for the opportunity. It’s so hard to get to the Stanley Cup Final. Every team you play is better than the team before. They made the Finals last year, so, they’re battle-tested, but we’ve got lots of playoffs games under their belts as well. We are battle-tested as well.

You’re nervous and excited to get going on Saturday, it’s really in the hands of the players, and the coaching staff.

I’ll pitch in my opinion here and there, you know, leading up, and after the games, but ultimately the coaching staff, Kris Knoblauch and his people make the final decisions on rosters and matchups and the players. Both teams are going through their preparations, but once you play head-to-head, then on Sunday, you’re making adjustments because now you’ve got a feel for what’s going on. From a management perspective, you’re a very, very small piece of what’s going to happen here over the next two weeks.

Holland’s contract expires at the end of June. When I asked about his future, he said he wanted all of the focus to be on the players and the task at hand. My sense is Holland won’t be back as the GM next season. He’s had a Hall-of-Fame career, and winning another Stanley Cup would be a great way to go out. Even if the Oilers lose, I view Holland’s tenure in Edmonton as very successful. The Oilers have become a top team, and Holland added a level of professionalism and maturity that I felt the organization didn’t have prior to his arrival. Much of that is off the ice and behind the scenes, but how he treats people matters.

Of course, having McDavid and Draisaitl is a massive factor in their success, but Holland filled out the rest of the roster. He added many pieces along the way that helped shape this team. Like every GM he had some misses (the Kassian and Jack Campbell contracts, to name a few), but he’s had more big hits in Hyman, Kulak, Ekholm and other solid acquisitions that have helped shape this roster.

I’m curious if he remains in an advisor role. The next two off-seasons will be massive for the Oilers franchise. Who is going to negotiate the contract extensions for Draisaitl, Bouchard and McDavid? Maybe he will just retire to spend more time with his wife, children and grandchildren and golfing.

Holland helped oversee the Oilers return to relevance. They went from an organization who made the playoffs once in 13 seasons, to now having played the second most playoff games over the past three seasons, and now with a legitimate chance to win their first Stanley Cup in 34 years.

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