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On Ken Holland’s Legacy with the Red Wings

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Detroit Red Wings Stanley Cup Victory Parade Photo by Gregory Shamus/Getty Images

With the recent departure of Ken Holland for Edmonton, we here at WIIM wanted to take a look back at his tenure in Detroit. Because there was so much to talk about, JJ and I decided to team up and have a two person “roundtable” type discussion.


JJ: Ok so I guess the starting question is where do we stand RIGHT NOW in terms of Ken Holland’s tenure in Detroit.

I’ll fully admit that when it comes to our corner of the fandom (both the WIIM Community and the parts of the Twitter community we’re most-familiar with), that I have always leaned much farther to the apologist side than the hater extreme. Even with that, I have for the past few years been ready for the team to move on from him; but, now that his exit is official and we’re left to make sense of things, I do find myself looking more for excuses to view his time fondly than for reasons to spit on his name. I find myself simultaneously missing Holland and glad he’s gone. I guess this is what a rebuild does to you, but it does feel like the right time to begin a new chapter for the organization and that this chapter could not truly have started with Kenny still around.

I’m really interested to see how the next five years plays out because my knee-jerk feel right now is that by the time the story of Ken Holland’s career as a hockey executive is truly complete, he is going to go down as under-appreciated. Honestly, it kind of makes me laugh because I couldn’t think of a more-fitting career epitaph for the longtime GM of guys like Nick Lidstrom, Pavel Datsyuk and Henrik Zetterberg. I also know full well I absolutely would not be saying this if Ken Holland hadn’t been joking when he said his retirement would take place about five minutes after Nick Lidstrom’s.

In the time leading up to that split, Ken Holland failed to steer the Red Wings away from the post-Lidstrom collapse. He tried to re-load the team and recapture the same magic he captured when the team’s core transitioned from Steve Yzerman, Brendan Shanahan, and Nick Lidstrom over to Pavel Datsyuk, Henrik Zetterberg and...welll... Nick Lidstrom; in that attempt he failed and found himself floundering through semi-contention while the ravages of time ate away at his team’s ability to make meaningful runs deep into the playoffs. Holland either became the unluckiest GM in the sport, the most-shortsighted GM in the sport, or just some unfortunate combination of those things. However, there’s also all that context we have to take into consideration (not to mention speculate heavily on how much is of it is true and to its true effect).

This is the biggest key for me: it’s not necessarily excuses for Holland, because that makes it sound like the mistakes made were somehow beyond his control or are acceptable on some level. I don’t feel that way. The story of Ken Holland after the Lidstrom retirement isn’t one of inexplicable blunders. Honestly, if it were then this whole ordeal would be much easier because he very likely would have been fired much sooner. But, you don’t have to reach too far to make sense of a whole lot of Holland’s mistakes based either on what we outright know or can reasonably surmise: the Red Wings have been owned by the Ilitch family since well before Holland took over and the family’s sports-loving patriarch was nearing the end while anchoring an empire built on consistent excellence in a city that’s been suffering from a diminishing population base for years. Ownership was nearing completion of a plan to create a transformative base for the entire city that was centered around a brand new arena for their cornerstone franchise (and I don’t want to get into the politics of the cynical/hopeful side of what motivated the Ilitches to this goal).

From a fan’s perspective, it’s not an excuse one has to accept, but I also feel it’s silly to simply ignore that the business optics of what was going on would motivate an edict that the team take unnecessary risks to push off a much-needed rebuild until a time that’s perhaps easier to manage financially (and, to potentially pay off with a championship run that could have paid enormous dividends during that timeline).

So if we accept the ownership edict to keep the streak alive as long as possible, how does that change the optics of what Holland actually did while running the team? I think the actions he’s taken since the Red Wings have been forced to drop the facade and admit they’re rebuilding has shown promise for Holland’s ability to do so and my naturally apologetic-leaning fandom does find me less-angry about how we got here. However, I have trouble describing exactly how many grains of salt I’m taking all of that with because at one point, I’d have to give credit to Ken Holland for playing 4D chess while signing deals like Frans Nielsen and Justin Abdelkader, and I just cannot find a way to suspend disbelief that heavily.

Peter: I also find myself more on the optimist side of the coin in general. Sometimes it feels like some of the defending I’ve found myself doing of Ken Holland in the recent past is influenced by what I feel to be overwrought vitriol in his direction. I found myself feeling defensive of his tenure in the wake of the negative onslaught on Twitter from some areas of Detroit and Edmonton fandoms, as well as from third parties.

Like you wrote above, that’s certainly not to say that he does not bear some blame for the current state of the team in term of the bad contracts that he signed. He absolutely does.

I don’t really have too much to say about the first few paragraphs you wrote because I agree with your sentiments. I think that when the dust settles years down the road, his legacy will be far more positive than negative. The issue currently is that a lot of the negative is in the recent past, which understandably leads to it taking up more space in the current conversation.

I did want to talk about the ownership aspect you brought up because I believe strongly that any analysis of Holland’s tenure in Detroit is completely undercut if one does not take the playoff streak and the (seeming) ownership edict to continue that streak into account.

Like you said (and I’m really hoping we find something to disagree on so this article is not just the two spidermen pointing at each other meme), some of his moves make more sense when viewed in that context.

I think that even with that being said, Holland certainly made mistakes that he didn’t have to. When I wrote about the Daley signing, I said that I liked Daley as a player, but I didn’t agree with the signing. The Abdelkader and Nielsen contracts have become large stumbling blocks in the way of moving forward with the rebuild.

I’m sure there are other earlier examples, but for me the Nielsen contract is the recent deal that was most affected by the “go for the playoffs every year mandate.” Datsyuk left. They missed on Stamkos. The team needed a player who could play 2C, and it was entirely understandable at the time not to count on Larkin being able to do it.

The contract is too much money and too much term, but the vast majority of the bigger UFA signings are (which is why I’m a major proponent of avoiding UFAs until the team is ready to contend.) It made sense in the short term, which I think both of us are arguing was what he was told to focus on. It didn’t make sense in the long term.

I want to transition to another topic that is often discussed by Red Wings fans, but I want to focus specifically on Holland’s impact on it: the defensive logjam.

I feel that even assuming the “playoff mandate,” a valid criticism of Holland is that he didn’t shift away quickly enough from what worked in the past in term of “over-ripening” prospects. We saw with Dylan Larkin, and more recently Dennis Cholowski and Filip Hronek that he was moving more in the direction that most of the NHL seems to be going in near the end of his tenure.

He made some good moves since the streak ended, such as buying out Xavier Ouellet, but roster decisions prior to that have hurt the team in a way that still needs digging out from.

For example, Libor Sulak and Joe Hicketts are both RFAs. Neither has played enough in the NHL for the management team to have a real view of what their NHL potential is. I certainly don’t think either is going to be an NHL star, but I don’t think it’s unrealistic to think that they could both be solid NHL defensemen. Villi Saarijarvi will be an RFA after this coming season, and it doesn’t seem like there will be the chance for him to crack the NHL roster this season, as the team is currently constructed.

Considering that so many of our defensemen are considered replacement level or below, not having open roster spaces to have some of these players get an extended look is a roster construction issue that I think is largely due to mistakes by Holland.

JJ: Yeah the defensive logjam is something that very much shatters the ideal of mistakes-with-a-complex-reason that we can get into with a lot of individual veteran contracts and trades. Holland either failed to draft and develop NHL-caliber defensemen or he failed the defensemen he drafted by stunting their development using “The Red Wings’ Way”—There’s potential for an argument that the general lack of success of those picks since leaving Detroit is an indication that me maybe just got unlucky with a WHOLE BUNCH of draft picks along the blueline, but that stretches credulity too far for me, and it ignores the possibility that the too-slow development process essentially turned them into lost causes. Ryan Sproul, Xavier Ouellet, Alexey Marchenko, Brendan Smith, Kyle Quincey, Derek Meech, am I forgetting anybody? Either those guys should not have been drafted in the first place or they should have been developed differently. The only one we can argue the Red Wings got acceptable value out of was Smith.

Like you mentioned, we haven’t really cleared that jam either. Sulak and Hicketts remain essentially limbo prospects where nobody can accurately value them because we simply don’t have enough to go on. This makes them simultaneously too-valuable to just cut ties with and not valuable enough to trade. With a new Finnish defender coming into the mix next season and Gustav Lindstrom pending a transfer across the Atlantic for next season, it very much looks like we’ll be counting on injuries to veteran D-men in order to fill out the roster, but are we going to be able to get enough data about the NHL viability of these guys before they age out of their primes? I mean, that’s no longer Holland’s problem, but it’s something that concerns me going forward.

Speaking of going forward, I want to punt it back to you to answer this question first because I want more time to think about it:

What are you rooting for in terms of Holland’s upcoming tenure in Edmonton?

Peter: I’m going to fair catch that punt and go back to something that I should have mentioned earlier. Pursuing the streak cost the team dearly in terms of high draft picks. The reason I wanted to bring that up is that I think it ties into your logical argument that either the team missed on a lot of defensive draft picks or that they weren’t developed properly (or a combination of both). I think it’s the combination option, but I do think that the dearth of first round draft picks is a factor.

Now, that definitely could have been inferred by those reading this based on the discussion of the cost of pursuing the playoff streak, but I wanted to make sure that I explicitly pointed that out, since I think it is a factor. That raises the question of how much of that is Holland’s fault, i.e. could he have continued to pursue the streak in a way that didn’t give up so many first round picks?

I’m going to say yes, but since this article is going to be very long already, I’m not going to go transaction by transaction. It seems like this could be a fruitful discussion for our community to have in the comments, and I’m interested to see the cases made for both sides of the argument.

To get back to your question: I want Holland to succeed as long as it’s not at the cost of Detroit.

I know from past discussions that you and I have different overall philosophies towards former players, etc going on to other teams. I’m of the mindset that as long as a member of the Red Wings organization left on good terms, I want them to do well as long as it doesn’t affect our team.

For example, recently, Tomas Tatar and Gustav Nyquist were traded. I’m glad to see them doing well with their new teams, although I’ll obviously root against them when they play Detroit.

In this same vein, I want Holland to do well in his new position. As we laid out above, he’s certainly done things that have hurt Detroit in terms of signing bad contracts, but I absolutely don’t think he did anything nefarious to cause me to wish that he crashes and burns in his next job.

Outside of that, I want him to do well in Edmonton because I think that having the best player in the world succeed is good for hockey in general. It’s certainly fun as fans of other teams to point and laugh at the ineptitude of a team that has been gifted high draft pick after high draft pick, but Connor McDavid plays a highly entertaining style of hockey, and that’s the type of hockey I want to see more of. While I absolutely do not buy into the idea of “having so many higher seeds losing in the first round of the playoffs is bad for the league,” I do think it’s bad for the league to not have its best player in the playoffs.

I want to be very careful about how I phrase this next part, because it’s mostly speculation, but there seems to be something very wrong in Edmonton other than the fact that they had a GM who was continually being fleeced in trades.

Even though much of my analysis has a basis in statistics, there are things that can’t be measured. A team’s culture is important, even though I think in some cases, it can be overemphasized.

I wish I could remember the name, but I heard an interview earlier this season with a former player who went from a team that was successful at the time to Edmonton. He talked about how different the culture was in a negative way. Now this was more than a couple years ago, but I can’t help but thinking there is something deep-seated in the Oilers organization that needs to change before they can find success.

The thing that convinced me this was the case was this season. They brought in Ken Hitchcock, who, regardless of what people might think of him as a coach overall has a very clear track record of instilling a style of play that leads to short term success. They still missed the playoffs.

Ken Holland is someone who very much believes in team culture, and assuming that he has the autonomy that is reported, I think he will have a chance to succeed. How do you feel?

JJ: I will say that my stance of “once he’s no longer a Red Wing, he can get bent” has softened quite a bit. I enjoy watching Gustav Nyquist have a good time, and I was really liking Tomas Tatar before he re-entered the Atlantic division. It really depends for me on how much I cared about them before they left. Calle Jarnkrok and Matty Janmark never established themselves as Red Wings, so they can get lost. I suppose I’d root against Riley Sheahan if he were better but I’m honestly just kind of sad about what’s happened to his career. Petr Mrazek is a personal thing that I’m still not going into detail about, but I do like the Hurricanes.

In terms of Holland though? I definitely agree with your point that Holland doing well in Edmonton with Connor McDavid is good for hockey, and I do want that. Mostly, the more I think about it, I want Holland to succeed in Edmonton so that it can accelerate the process where I’ll be able to look back on his entire tenure in Detroit without grimacing over what’s happened during the Wings’ collapse. I guess when you boil it all down, I’m rooting on hindsight telling me I was right to believe that a bunch of the mistakes weren’t entirely his fault.

Before we wrap this up, I just realized there was another line of thinking I maybe wanted to get into, but I’m not sure it’s worth shoehorning into the discussion at this point.

The idea of Ken Holland being “pushed out” is interesting to me. It’s easy to look at his quotes and what actually happened and see that those two narratives don’t really seem to match up. He loves the Wings, he wanted to get Steve Yzerman back, but he also left to take over the GM job of another club in less than two weeks? It just doesn’t feel right.

However, I do think there’s a way to manage that into a narrative that does bridge these two ideas, and I think that goes back to the theory of the playoff mandate: If Ken Holland knew he was lying to the fans trying to sell a streak he didn’t really want to keep alive, then he also knew that these last few years absolutely WOULD become the years that the Red Wings’ fanbase would largely turn on him.

It’s not like it matters terribly much, but we’ve all joked to varying degrees about seeing Steve Yzerman doing things that we know Ken Holland would have done and having a completely different outlook on such a signing/trade/announcement. If part of a GM’s job is selling the team to the fans, then knowing you’re not the guy who’s capable of most-effectively doing that has to be a hard-turn realization.

”If you love something, let it go” may ring a bit treacly here, but it does allow one to fit the narrative that Ken Holland sincerely loves this franchise but also loves being a GM and what’s ended up transpiring here is a mixture of making both of those loves work. I will also fully admit that this once again sounds like Ken Holland playing 4D chess and jumping on a grenade for us and, as such, I’m not sure how much I want to believe such a narrative.

Peter: Yeah, there’s been a lot of discussion about that since the Yzerman move was announced, and specifically following the press conference, during which Holland appeared to be on the verge of tears. We talked about this on the latest edition of WIIM Radio.

I think that ultimately, the more I think about it, it doesn’t really matter to me if he was pushed out. I mean, I don’t want to say that I don’t care as a person who possesses the ability to empathize, but from the perspective of someone who cares about the Red Wings, it doesn’t make much of a difference either way.

I think you can certainly fit the publicly available facts into a narrative that Holland was pushed out, but I also think you can fit them into a narrative that his quote in the recent Sportsnet article is true (or mostly true):

What did it feel like when Chris Illitch told you that Steve Yzerman was taking over the GM job in Detroit?

“I would say to you (pauses)… I did that. I went to Chris during the season, and I said, ‘It’s time for a leadership change.’ I had asked people in that organization for a lot of years to sacrifice? It was my turn to sacrifice. I had 22 incredible years.

“As you get to know me, I’m very, very passionate, I’m very, very loyal. I try to treat people with respect. At the end of the day, I knew. I knew it was time to hand the keys to Steve.”

Of course quotes like this have to be taken with a grain of salt, but as we talk about so often, that’s not abnormal when trying to guess what’s really happening based on quotes from a GM, coach, etc. It’s important to also include something you brought up outside of this article, which was that the above quote is Holland “getting to write his own exit narrative.”

Holland could have been pushed out, but the facts could fit into a narrative in which Holland is telling the truth in the above quote (or an exaggerated version of the truth):

The reason he was so emotional could have been because a large portion of his life was drawing to a close, whether or not he stayed with Detroit longer or not. This narrative lines up with reporting from before the Yzerman announcement that he was upset at how the fans were reacting to his decisions over the past few seasons. It lines up with sightings of him and Yzerman together at the same event, scouting.

His leaving to be Edmonton’s GM can fit into that narrative too: He loves being an NHL GM, but he felt that it was time for him to give up the reins in Detroit. He stayed with the team, but eventually wanted to pursue GM opportunities. The reporting on the Edmonton GM search was that Holland wasn’t even a candidate until the very end. It also sounds like Edmonton approached him, as opposed to him pursuing the job. The opportunity to keep doing what he loved, plus a very lucrative contract was too good of a deal to say no to.

I believe more in it being his choice than him being pushed out, although I fully admit that I’m assembling the pieces the way I think makes the most sense. I could very well be wrong.

I guess since I took the time to write all that out, I do care at least a little about what happened. Ultimately, I don’t think it affects the team.

We both agreed that we want to see Holland do well in Edmonton. What would your ideal scenario be?

JJ: What I want to see is Steve Yzerman’s Red Wings sweep Ken Holland’s Oilers out of the Stanley Cup Final.

Peter: Hard to argue with that!