Looking Back At Ken Holland’s Five Year Oilers Tenure

When I released my Trade Deadline Recap in March, I said that my overall view of Ken Holland as the General Manager of the Edmonton Oilers would come down to how his last roster did in this year’s Playoffs. Three months after being underwhelmed by his Trade Deadline Day, he was OH SO CLOSE; he only needed one more win. He didn’t get it, though. At the end of the day, that’s what most people will think more about. The Stanley Cup needed to be the cherry on top. But how “bad” per se was he?

Some of the big names in mainstream Oilers media talk about him as if the Pope should declare him a saint. A lot of Oilers fans talk about him as if he’s worse than the Devil. It’s hard to find a middle ground between two extremes on such a polarizing topic. Though I try to have a more neutral opinion, it is fair to believe that just being good enough is no longer good enough. Again, Holland just came up short. But I’m left scratching my head whenever someone online says he’s “Worse than Chiarelli.” That’s a pretty weird way to critique a Cup Final appearance, compared to only one Playoff appearance in general through 4 years from the former. It’s a funny job to critique because even if they do all or most of the right things, there are no guarantees in the Postseason. There are lots of good GMs, great GMs, who build rosters that finish high in the Standings and should win it all on paper. But then, for whatever reason, they just can’t get over the hump, and they always have early Playoff exits. Sometimes, a team makes a deep run after barely clinching the last Playoff spot. Sometimes, a team wins the Cup with a rookie, backup, or third-string goalie turning into a Playoff hero. I’m not saying this to make excuses, that’s just how hard it is to win in this league. The shiniest looking team isn’t always the most successful. Going on longer runs is what gets more favorable reviews. Did I agree with all of Holland’s decisions? Not 100%, but that’s every GM. They won’t get every single thing right all the time. Was I praying for Holland to get a contract extension? No. Do I also think he’s been over-hated? Yes.

A week after losing Game 7, starting the offseason, I felt like giving my two cents on five separate points in the five years that Holland spent in Edmonton. As this has all been typed, and as it gets published, Jeff Jackson’s work this summer will not be accounted for. That’s for a different article all together. I’m solely talking about the days between Holland’s hiring and the moment Game 7 was over.

The Draft: This first point is still sort of too early for me to tell, and sadly, not every prospect winds up being on your NHL team or even a full-time NHLer in general. However, my optimism for it now is cautiously higher than it was a year ago. Because we as a fanbase grew too accustomed to picking First Overall, it’s easy for us to sometimes forget that most prospects take longer to mature and properly develop. It doesn’t mean that they’re total busts or you kept picking the wrong guys. Not being Alex Ovechkin doesn’t mean they’re going to be Alex Daigle. Admittedly though, this is where Peter Chiarelli does have Ken Holland beat so far. Evan Bouchard, Stuart Skinner, Ryan McLeod, and Vincent Desharnais were already part of the organization prior to 2019. If drafting were the only thing Chiarelli did, he’d be given a more favorable rating among Oilers fans. Holland’s prospect pool still requires a wait-and-see approach. Xavier Bourgault(22nd in 2021) put up great numbers in the Quebec Major Junior Hockey League but is having offensive struggles in the American Hockey League. I’d give him at least one more season down in Bakersfield and, if he’s showing more promise, perhaps a brief 2025 Oilers audition. If not, he will be viewed more as a bust. Tyler Tulio(126th in 2020) and Carter Savoie(100th in 2020) are similar to Bourgault but also haven’t had the ideal size for how this new Oilers team looks. You can have 1 or 2 Jonathan Marchessaults, not 20. One selection I really liked last summer was right-handed defenseman Beau Akey(56th in 2023). If his shoulder injury hasn’t messed him up too much, I’d be more than content with him turning into a 30-35 point player, as long as he’s also competent defensively. Maybe Luca Munzenberger(90th in 2021) and (Max Wanner(212th in 2021) sound good for third pairing depth. Before this year’s Playoffs, I started leaning my way into the Trade Philip Broberg camp. I mean no disrespect to Desharnais, but I felt that after the 2019 8th pick lost out on a third-pairing spot to a 25+-year-old rookie, that was the end of the Edmonton road for him. He went from being the most despised Draft choice in five years to being an unexpected postseason hero starting in the second half of Round 3. He was the team’s third-best defenseman, averaging close to 20 minutes a night on his offside and even killing penalties. Moments of inexperience were still expected, but if he continues his postseason play next season, it looks promising for the team’s Top 4. Dylan Holloway (14th in 2020) had really shown a spark as a second-line forward these couple of months. He scored some key goals, 2 of them were on the 4th line in Round 1. He blocked shots and threw hits. The Oilers need to strike gold with the last two prospects I’ve just mentioned. If possible, I’d also like to see Raphael Lavoie(38th in 2019) and James Hamblin(Undrafted)/signed in 2020) as the 13th/14th forwards on the team. Part of my concern with Edmonton’s Draft record is their long-time age bias with Game-Day lineups. I understand they have a history with a select few young players who didn’t pan out. But at some point, you have to loosen the leash a tad and not be so paranoid about how they look. Just because they go one game or two without getting a point doesn’t mean they suddenly got worse. Holloway needs to stay a Top 6 forward, and Broberg needs to stay a Top 4 defenseman. We’re not asking these guys to be McDavid, Draisaitl, and Bouchard. We just want them to be trusted with bigger roles. It’s especially crucial in a salary cap league where you need solid players on cheaper contracts and ELCs. I’m really hoping that this recent Cup run will make the coaching staff confident in using them more. If current Condors players are concerned about their futures in Edmonton, they can look to the aforementioned Desharnais as an inspiration.

Trades: Most of the time, he didn’t like paying a lot for pure rentals or parting with picks and prospects. Chiarelli was too willing to make risky trades, and Holland wasn’t willing enough. Acquiring Mike Green and Andreas Athanasiou was his first Detroit Nostalgia moment. Green only played 2 games for Edmonton due to injury and Athansiou was a AA battery that never recharged. Also, sprinkle in the likes of Dmitry Kulikov, Tyler Ennis, and Derek Brassard. I initially hated the Duncan Keith trade because he was well past his prime as a player, and I didn’t like his cap hit. But he retired before his contract expired and Bouchard appreciated having him as a veteran leader to learn from. So I no longer feel as spiteful towards Keith’s time on this team. Warren Foegele put up respectable numbers in the regular season, but that was mostly on the part of playing on Draisaitl’s wing. He’s struggled to produce consistently in the Playoffs, though productive in the Cup Final, he was. We don’t like that the pick we traded for Brett Kulak was used on Lane Hutson, but he has been a solid third-pairing defenseman who can also slot into the second pairing if need be. Holland’s best trade, without debate, was for Mattias Ekholm. It cost Edmonton Tyson Barrie, who signed with them in the summer of 2020, a couple of draft picks and a pretty good prospect in Reid Schaefer. There is no understanding of what Ekholm has done for this team’s blueline. He and Bouchard have been one of best pairings in the league since he was acquired. Moving Barrie also made way for Bouchard to take hold of the Top PP spot and shine even more as an elite offensive defenseman. It was the franchise’s best trade since Chris Pronger. Klim Kostin and Nick Bjugstad were good in their bottom six roles, Kostin became a fan favourite, but both chose not to re-sign. There was poor luck due to a pair of this year’s Deadline acquisitions dealing with injuries. Troy Stecher never even practiced with the team from April onward, as he had surgery on a cyst in his leg. Adam Henrique cost Edmonton a first round pick and missed all but one game in Round 2. Since coming back in Round 3, he was a very effective third line center. Sam Carrick was good for faceoffs and physicality. But not using him in the Finals against a strong Florida team tells me it’s not worth giving him a future here. The most impactful “Addition By Subtraction” trade was Milan Lucic going to the Flames for James Neal. The Oilers were able to buy out Neal’s contract in the summer of 2021 and use the spare money on their greatest free-agent signing ever.

Free Agency: Zach Hyman is the face of Holland’s offseason signings in Edmonton. I don’t think anyone expects him to score 50+ again, but watching him play always feels like Ryan Smyth came out of retirement. A hard-working winger who goes to the dirty areas for goals and never takes a shift off. But for every Zach Hyman, there is one Jack Campbell. This is the only move in my mind that ever had any impact on Edmonton’s position in the Standings. Soup was supposed to be either the #1 goalie or share a 1A/1B situation with Skinner. All he needed to do was just be league average at best, but he kept allowing beach balls two seasons in a row. $5M a year for a guy we sent down to the AHL? Yikes. His consistently bad play forced Skinner into a position where he had to play too much early and burn out often. Calvin Pickard, another Holland signing who was actually supposed to be the AHL backup/3rd string goalie, thankfully helped save them between the pipes. I felt confident that Game 4 against the Kings in 2023 would be enough to boost Campbell’s confidence this past season. I’ve said many times he deserved more 2023 Playoff starts to help Skinner reset, just as Pickard did in Round 2 this year. But alas, this experiment exceeds the word dud, and we collectively owe Mikko Koskinen an apology. When Cody Ceci isn’t putting on Game 7 magic, his minutes paired with Nurse feature the worst displays of Oilers defense I’ve seen since Justin Schultz, and that is saying a lot. Both the eye test and analytics mutually agree that those two are better separated. Nurse does too much to compensate for his contract and Ceci is not a Top 4 defenseman. It took until Round 3 to finally unstaple them every game. While Mike Smith handled the puck too much for my liking, making for some hilarious gaffes we can all laugh at now, he didn’t have the worst 3 years as Edmonton’s starting goalie. That being said, he was getting noticeably worse the longer the 2022 Playoffs went on. Tyson Barrie was the first defenseman in NHL history to not get a Norris trophy nomination while leading all defensemen in points during the 2020/2021 season. That’s a very telling indicator for which type of player he was. While he did improve somewhat defensively in 2022/2023, as I stated in my Trades point, he needed to be moved for a much bigger need on the team. Derek Ryan has been a steady leader for their bottom 6, Mattias Janmark and Connor Brown were penalty kill magicians in this past Cup run. During the regular season, you could play a drinking game for every time those two failed to capitalize on a breakaway or odd-man rush. But they eventually became clutch scorers at the right time. Brown, in particular, finally found his legs after all the patience we were losing with him getting back into foot speed due to the leg injury he had last season. The bottom 6 took pride in what they did on the ice despite the fact they weren’t always scoring a lot. Derek Ryan was once asked a question during the regular season about their need to score more. His answer was how they consistently draw penalties to help the team’s stars score on powerplays but that it was never talked about by reporters. The bottom 6 came alive in Rounds 3 and 4, but that’s still an interesting player perspective to consider. I liked Evander Kane during his first half of a season in Edmonton, in spite of how controversial that signing was at the time. He started his Oilers career with nearly a point in every game, and seemed to be putting his past drama behind him. With his swagger, physicality, and goalscoring, he was exactly what their Top 6 needed at the time. But he’s, unfortunately, had his production and effectiveness get slowed down by injuries, the most notable being his slit wrist in November of 2022. He’s a trooper for gutting out those injuries, was arguably their best forward in November, and good in the Vancouver series. But he wasn’t even healthy enough to play in the Finals this year. At his age now, with all those bruises, it’s hard to still see him as a top 6 forward anymore. We can only imagine how much more a healthier Kane could’ve done the last two seasons. For all the jokes about Corey Perry losing in all of his most recent Cup Final appearances, he still proved to be a great veteran presence for the team. He can’t really keep up offensively anymore, but I think the leadership group will forever value what he brought to them this season. Sam Gagner felt more like a nostalgia signing, and it was really special how he came back from double hip surgery. But I don’t see him being useful as an extra forward, give that duty to someone younger. Oh, we’ve also had Devin Shore and Adam Ernie. Cool, I guess.

Salary Cap: Outside of the Lucic/Neal trade and Neal buyout leading to the Hyman signing, this is admittedly Ken Holland’s most visible shortcoming to discuss. Three of his four Stanley Cups in Detroit were won before the NHL introduced a salary cap. He has struggled to adapt to this style of team building and, let’s just say, doesn’t always spend his money wisely. Also understand it’s not just about the total dollars, the number of years on a contract can make it more problematic. Every Oilers fan’s biggest indicator of this is Darnell Nurse’s current contract with six years remaining on it. Now, for the record, it’s not necessarily the $9.25M cap hit that I blame Holland for. It’s the bridge deals Nurse was getting before his market inflated that I blame Holland for. I think after Nurse’s first bridge deal, signed by Chiarelli, Holland should’ve signed him to a much longer contract instead. Handing out a second bridge deal and not taking into account the risk of any player’s value suddenly increasing was totally irresponsible on his part. Nurse benefitted from really good production in the Canadian Bubble division during the COVID-19 Pandemic. Seth Jones and Zach Werenski were also given big contracts that year. It’s worth noting, however, Edmonton lost both Oscar Klefbom and Adam Larsson for reasons they couldn’t control. When they traded for Warren Foegele, it cost them Ethan Bear. Losing what used to be your Top pair in one summer sometimes makes it hard not to overpay. Yes, I do take into account that he, McDavid, and Draisaitl are the best of friends. The best Edmonton can do with him is find a good partner that’ll take pressure off of him. Holland also gave Zach Kassian a 3 year extension that paid him over $3M per season in 2020. The basis for that was Kassian having a career year offensively while playing with McDavid and Draisaitl. And with two suspensions that same season, he stopped adding his physicality to his game, so he couldn’t even be effective that way anymore. He became useless, and trading him in the summer of 2022 still doesn’t erase how bad of an idea that extension was. I’ve already mentioned Kane and Campbell. The terms for both of those players would’ve been fine if Kane’s body hadn’t worn out and if Campbell wasn’t Swiss cheese. Fans want to see just a tad more creativity with cap spending in the near future. Connor Brown got a $3M+ performance bonus after playing ten games this past season. That’ll be another thing for management post-Holland to maneuver around.

Culture: This final point doesn’t always get much appreciation, and that’s partially because it can be overexaggerated sometimes. But it is Holland’s strongest point, and I have a feeling that after this past season, people may appreciate it just a little more. Despite his mistakes, and he’s had them, this is what he excels at the most. Much to the chagrin of Oilers fans, including myself, we didn’t always see the big headline-making deals. It is true that some targets still preferred other teams over Edmonton, we sometimes forget that the players we want also have to want to play for our team. But Holland mostly respected the comradery in the Oilers locker room. It was a controversial decision to keep Cody Ceci at the Trade Deadline, but the leadership group wanted that. You can’t hang onto every friend you make for so long, some tough calls need to be made. But it was a very tight group, the tightest we’ve seen in Edmonton in a really long time. You always hear it in the interviews with players about how much they’ve grown together and the lessons they’ve had to learn through Playoff disappointments. In 2021, Kulak and Hyman were on opposite ends of a first round comeback/collapse. Perry was also on the winning side. Having teammates with different perspectives on the same series can be beneficial, as we saw in this year’s regular season and Playoffs. Holland may not have brought in the flashiest people, but he brought in the right people. It’s kind of similar to when you work a 9-5 job. How well do you perform tasks with your boss and fellow employees? Are you building a strong and professional relationship that presents a wider range of ideas? Having an overabundance of highly skilled players with big point totals isn’t worth celebrating if they frequently underachieve and lose the first or second round every year. Neither is having 20 BFFs worth celebrating if they all move slower than snails. Rather than asking “Statistics OR Culture”, you need Statistics AND Culture. It was reported during this month’s Cup Final that Mattias Janmark opened up with a speech about what Edmonton needed to do to turn their season around after their Carolina loss on the road in November. I could never imagine this team handling adversity like that during the Decade Of Darkness. Of course, the Cup is the goal, but you learn to appreciate the journey as you get older. Considering where they were at the end of the 2018/2019 season, I have a hard time saying this five-year tenure was quote-unquote terrible. Holland took a franchise that was still finishing as a bottom 10 team with two 100+ point players, got them to make the Playoffs every season, built them a window to contend and they came just one win away from winning it all. Wishing the window was built sooner, even in hindsight now, wasn’t a realistic expectation. If all your team does is miss the Playoffs before a managerial change, why would our preferred trade or free agent targets want to play for our team? Until now, nobody was taking them seriously. They needed to learn how to get better first. Now that they have, they did just become a popular option for free agents and trade targets. Some people will still say that the Oilers were just a one or two man team. But you don’t post the best penalty kill in the Playoffs with just one or two men. A team that used to try winning every game just with offense became comfortable playing tight one goal defensive games and keeping leads. They learned how to not give up when their backs were against the wall. If your argument is they had all the pieces before Holland took over, they also had good pieces when Chiarelli took over. How did that pan out? We had good young players get hindered by a losing environment many years ago, and that could’ve easily happened again with one of Bouchard or Skinner. I understand we were once heavily scarred by the Steve Tambellini era, the Dallas Eakins era, and the Peter Chiarelli era. But we’re no longer in those eras. You don’t see that in Edmonton anymore. Opposing teams view the Oilers in a different light now. Losing Game 7 of the Stanley Cup Finals by 1 goal is the most heartbreaking loss, but it’s far from the worst. After all the years this franchise spent being a basement dweller and the punchline for Draft Lottery jokes, recognizing the big improvements on and off the ice shouldn’t be controversial. As Ryan Nugent-Hopkins stated, it’s the most proud he’s ever been to be an Edmonton Oiler. If they keep building on this past season, we’ll one day talk about that heartbreaking 1 goal Do-Or-Die loss switching to being a joyous 1 goal Do-Or-Die win. Ken Holland started it, and now the new management team is tasked with finishing it. Connor McDavid and Leon Draisaitl aren’t the first couple of great players to lose their first Cup Final. A lot of NHL greats and a lot of great teams needed to have growing pains and tough losses, too. As long as those two remain in Edmonton together, I firmly believe this past season won’t be the last time they go far in the Playoffs. 

We Got The Jack Inside The Rink

In episode 8 of the Inside The Rink podcast, Matty and Smitty are joined by new co-host Conrad Jack. After the long hiatus, we get back to hockey with a PACKED episode!Matt Rempe & the Devils vs. Rangers Line BrawlCould the Vancouver Canucks squander a playoff opportunity? Have the Winnipeg Jets finally figured out their lines?Flyers Head Coach John Tortorella is a sound byte MACHINEOvechkin is on his way to 895, Who is next?McDavid joins elite company with 100 Assists in a seasonRyan Hartman was suspended 3 Games, was it worth 3 games??Can Auston Matthews hit 70 Goals this season?The Eastern Conference Wild Card race is heating up, who lands the two playoff berths?For all of your hockey news and more from the show, visit us at insidetherink.com and watch us on YouTube! How to support us and our sponsors:TicketmasterColumbia Sports ApparelESPN+ SubscriptionFanaticsDraft Kings – CODE ITR
  1. We Got The Jack
  2. Episode 7. Player Safety First!
  3. Episode 6. Early Trade Season
  4. Episode 5. Longing For The Chiarelli Years
  5. Episode 4. Ottawa’s On Fire

Stephen Vani

Oilers fan in Toronto. Staying up past my bedtime for Western games since the mid 2000s.

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