The Worst of Ken Holland Tournament of 32 Preview

At this time of year the DSR usually starts the grueling preparation for the Worst Detroit Sports Media Personality Tournament. But I have decided to push that event back to the baseball All-Star break week for two reasons.

One, I am a little burned out from the Raggies presentation and preparation. And there are too many similarities between that awards ceremony and the Worst Personality bracket.

Second, by the All-Star break, the Tigers will probably be 38 games behind the Indians in the Central and that tournament will at least be SOMETHING to look forward to before the Lions report to training camp.

[Matt Patricia!!!! Goooooo Lions!!!!!]

So instead, I chose to run a bracket mocking Ken Holland. We are going to decide the worst of the worst when it comes to the Red Wings GM in a tourney of 32 options.

We have broken down the bracket into the following regions:

The Trades
The Quotes
The Signings
The Absurd

And while 97.4% of the entries occurred in the post-Salary Cap era, which Holland has completely botched, there are still some doozies from the Cup days.

The matchups will commence on Twitter on Thursday, but in the meantime, here is a thumbnail sketch of each of the contestants.


1] The Kyle Quincey Debacle

In 2009, the Red Wings had to make a decision. They needed to get rid of a defenseman. The choice came down to Quincey, Derek Meech and a 78-year-old Chris Chelios.

Holland idiotically chose to waive Quincey who was quickly picked up by the LA Kings where he had moderate success.

Then at the trade deadline in 2012, Holland decided he needed a defenseman so he acquired Quincey for a FIRST-ROUND SELECTION.

That pick eventually ended up in the hands of Steve Yzerman and the Tampa Lightning.

With that selection, the Bolts took Andrei Vasilevskiy. Who will almost assuredly be a Vezina Trophy finalist for best netminder this season.

2] The David Legwand Trade

At the deadline in 2014, Holland wanted a center because the team was ravaged with injuries up the middle.

So he acquired the Corpse of David Legwand. The Detroit native was a pending unrestricted free-agent. In 21 games, Legwand scored four goals and was a defensive liability. The team made no effort to re-sign him that summer.

In exchange the Wings sent Nashville Calle Jarnkrok, Patrick Eaves and a conditional draft pick that ended up being a second rounder.

Jarnkrok developed into a very solid two-way forward for a Stanley Cup contender and Eaves turned himself into a 30-goal scorer. And that’s before you even get into the 46th overall pick they sacrificed.

3] Holland Has Made ZERO Blockbuster Trades Since Hasek/Kozlov

Not since agent Rich Winter contacted Holland and told him that Dominik Hasek only wanted to play in Detroit has the terrified GM made a game-changing deal.

While his former proteges (Yzerman and Jim NJill) seem to make one every season.

4] The Erik Cole Trade

Another horrendous deadline move for a pending unrestricted free-agent. Sensing a pattern here?

Cole played 11 games for the Wings before suffering a career-ending injury.

In return for Cole, the Dallas Stars received Mattias Janmark, Mattias Backman and a Mattias To Be Selected Later in the Second Round.

Janmark has played 121 games for Dallas and has registered 27 goals and 28 assists.

5] Not Trading Valtteri Filppula for a 1st-Round Pick

Nearing the trade deadline in 2013, Holland went on the radio in Toronto and bragged to Greg Brady (formerly of WDFN) that he could procure a first rounder for pending UFA Filppula.

To make matters worse, Holland had a replacement for Filppula in Grand Rapids who was ready to go Tomas Tatar.

Holland passed on the first rounder and then made no effort to re-sign the Finnish forward that summer. But I don’t want to spoil the rest of this disaster until later.

6] Not Trading Jiri Hudler for a 1st-Round Pick

Holland never knew what to do with Hudler. He lowballed him in a contract negotiation in 2009, which led to “Happy” taking his talents to the KHL for an entire season.

When he returned, Hudler developed into a consistent scorer. Approaching the deadline in 2012, Holland could have received a first rounder for a guy who scored 25 goals that season.

He passed though, and made zero effort to re-sign the miniature winger that summer.

This becomes a bigger nightmare when we get to the “Signings” Region.

7] Not Trading Jimmy Howard When He Could

The Wings longtime goaltender was coming off a pretty good season in 2015 (2.44 GA, .910 save percentage) and was a decent trade chip considering his moderate salary.

Holland could have easily swapped Howard for some desperately needed cap space but passed.

The failure to move on from Howard has totally stunted Petr Mrazek’s growth and now the team is left with no goalie of the future.

It’s comedic that Mrazek is coming off of back-to-back shutouts as I write this.

8] The Bill Ranford Trade

The Wings were looking to win their third straight Cup in 1999 and Holland decided to go all-in at the trade deadline.

They acquired Chris Chelios, Wendell Clark, Ulf Samuelsson as well as Ranford to add depth behind Chris Osgood.

(In an unrelated note, I played blackjack at the Windsor casino the night after they all arrived in town — with the exception of the fuckhead who took out Cam Neely’s knee.)

The Wings easily dispatched of the Ducks in the first round and then faced a matchup with the hated Avalanche in the second round. Unfortunately, Osgood was injured in that Anaheim series.

After going up 2-0 against the Avs, Ranford couldn’t stop a beachball the rest of the series and the Wings lost four straight because Holland didn’t acquire a reliable backup.

Thus ended any hope of a three-peat™ (Pat Riley).


1] Franzen Over Hossa

The decision to prioritize the signing of Johan Franzen over Marian Hossa was ALWAYS A DISASTER, which really began the downfall of Holland, but the subsequent results earned this decision a #1 seed.

While Hossa continued his Hall of Fame career in Chicago racking up Stanley Cups with Scotty Bowman, Franzen became an unreliable, streaky goal scorer who unfortunately suffered numerous brain injuries, leading to the end of the “Mule’s” career.

This one makes you sick just typing it.

2] The Chychrun/Cholowski Debacle

Holland decided to swap the 16th overall selection to Phoenix for the 20th pick so he could rid himself of Pavel Datsyuk’s contract.

A contract Holland had signed with Datsyuk while knowing full well that #13 was itching to go back to Russia.

Holland wanted Datsyuk’s cap space so he could make a run at Steve Stamkos. Of course, the Lightning superstar never had any intention of leaving TB for Detroit.

Stamkos visited with a handful of teams that summer and Detroit wasn’t among them. The city had a better chance of getting Amazon HQ2 than the 50-goal scorer.

After losing out on Stamkos, Holland blew that cash on Frans Nielsen and re-signing Darren Helm.

The Coyotes quickly snatched up one of the best defensemen available in that draft (Jakob Chychrun) while Holland settled for Dennis Cholowski.

Chychrun became a regular in the NHL as a DEFENSEMAN at the tender age of 18 and is well on his way to becoming a top pairing D-Man.

Meanwhile, Cholowski failed at St. Cloud State and then couldn’t even make the Canadian World Junior team this past Christmas.

At least he met his girlfriend in college.

3] Overripe Youth

While the rest of the league figured out that in the cap era that you needed to get your prospects to the NHL as quickly as possible to assist with budget constraints, Holland still stuck to his “overripe” theory.

Nothing personified this asinine and antiquated thinking more than Gustav Nyquist and Tomas Tatar playing a total of 402 (!!!!!!!) games in the AHL!!!!!!

Because who couldn’t have used Tatar in the 2013 playoffs when the team blew a 3-1 series lead against the eventual Cup champion Blackhawks?

Tatar was too busy scoring 16 goals and leading the Griffins to a Calder Cup because who the fuck cares?


4] Signing Free-Agent Senior Citizens

During their dynasty years, the Wings had tremendous luck with over-the-hill players. Larry Murphy, Chris Chelios, Freddy Olausson, Mathieu Schneider, Brett Hull, Igor Larionov, Luc Robitaille, etc.

Holland never grew tired of this blueprint.

(Actually this Wings’ strategy predated Holland. Just ask Darryl Sittler, Borje Salming, Rick Green, Bernie Federko ….)

Guys like Mike Modano, Todd Bertuzzi, Daniel Alfredsson & Brad Richards were brought in to play important minutes and were well past their primes.

Holland refused to adapt to a game that was becoming younger and faster. The Modano signing was a disaster. Bertuzzi prominently appears on the Mount Rushmore of slow linemates Datsyuk was forced to play with.

Alfredsson (drastically overpaid) had a decent year, leading an injured Wings team in scoring. Richards was basically quarterbacking one of their PP units the entire season. Then retired days after their first-round loss to Tampa.

An important side effect of these “roster cloggers” was they made it virtually impossible for young players in Grand Rapids to break through.

5] Fucking Over Andreas Athanasiou

Great strategy! Play hardball with one of your most dynamic offensive players. This was never about money. They’ve treated him horribly, on and off the ice. Because why not splurge on Luke Glendening while making your best 5-on-5 scorer play for peanuts?

The double standards at play within this organization are astounding. I have no problem if a coach wants to sit a player or cut his minutes in an attempt to rid said player of bad habits. Just be consistent.

You can’t tell me AA’s pitfalls are any worse than those of Darren Helm or Justin Abdelkader. Look at the money and term that’s been thrown around here. But THIS is where you draw the line?

The most entertaining part of this saga was Holland repeatedly telling anyone who would listen, “This isn’t a cap issue, we’re fine.” And then Riley Sheahan was promptly dealt to make room for AA.

6] The Dan Cleary Obsession

Cleary was close to never becoming a Red Wing. As the story goes, coming out of the lockout the Wings had one spot left at training camp. Holland had promised Dan’s agent a PTO for him. Babcock preferred Kyle Calder though. Holland ultimately prevailed in what would be his first, last and only argument win over Babcock.

A few positives: Cleary rejuvenated his career, overcoming the demons which plagued him during his younger days. He hit the 20 goal mark three times while in Detroit and scored some big playoff goals. He had 12 points in 18 games during the 2007 playoff run and 15 points in 23 games during the 2009 postseason.

The Flyers allegedly had a three-year offer on the table when he became a UFA. But Babcock didn’t want to lose him, enlisting several players to speak on his behalf. The end result was Cleary playing in 117 games over the final 3 years he was here, for 14 goals and 11 assists. The whole situation became a punch line among Red Wing fans. Yet another “roster clogger.”

You want to know why Tatar was the Crash Davis of the AHL?

Holland’s refusal to be his own man and part ways with Dan Cleary.

7] Overpaying 4th Liners

Even the most basic of tasks, filling out the bottom of your line-up, baffles Ken Holland.

4th line guys are the most readily available commodity EVERY off-season and trade deadline. If you wait long enough, you can find steals late in the summer. But Ken hates uncertainty. Guys like Steve Ott are signed just seconds after the clock hits noon on July 1st.

What’s the rush? Where’s the fire?

There are literally dozens of players in the AHL who can provide the same contributions as Luke Glendening and Drew Miller.
For a team that relies solely on the eye-test, how can you keep getting these moves wrong? Four years for Glendening should probably have its own seed. And to make matters worse, the brain trust thinks that skilled players on the roster, guys like AA and Martin Frk, need to cut their teeth grinding it out with these below replacement players.

You could make the argument that Detroit is currently spending over $13M on what SHOULD be their 4th line (Helm, Abdelkader, Nielsen).

8] Thomas Vanek for a 3rd rounder

Vanek is the perfect example of a signing you make while in the midst of a rebuild. A low-risk, high reward player on a one-year deal that can be flipped for assets at the deadline.

(SIDEBAR: His shootout prowess likely cost the Wings 3 to 5 points worth of lottery balls.)

Vanek finished with 38 points in 48 games for the Wings and was ranked high on virtually every trade deadline availability list except Florida’s.

A 3rd-round pick and career AHLer Dylan McIlrath was all that Holland could muster in exchange for Vanek. The same return Tomas Jurco fetched.

Patrick “Throw In” Eaves netted Dallas a 2nd-round pick. Yzerman got a 2nd rounder for Brian Boyle.

After spending years being the main reason for a seller’s deadline market (Quincey for a first rounder, Cole and Legwand for a King’s Ransom), he couldn’t even get a SECOND for Vanek. Unreal.

The Quotes

1] “These rebuilds don’t take two or three years. Once you go down that path, be prepared for eight, 10, 15 years.”

This gem came from Holland’s mouth on March 2, 2017. At the time, the Vegas Golden Knights didn’t exist. Ten months later VGK are the #1 seed in the Western Conference.

But Holland thinks REBUILDS take up to 15 years. Well, maybe with him at the helm (pun intended) they do.

It wouldn’t take 15 years for the Wings to rebuild if their team plane crashed into the Rocky Mountains.

2] “I am going to give you a history lesson.”

This condescending quote from Holland was delivered on 97.1′s “Jizz Bucket and Back Hair” Show.

Holland proceeded to explain how every defenseman on the team from 1991 to 2017 was acquired. Why? We still don’t know, other than that Holland was filibustering.

The real history lesson is this ….

You became the GM of this franchise in 1998 after the first Cup and you were gifted Steve Yzerman, Sergei Fedorov, Nick Lidstrom, Brendan Shahanan and Mike Ilitch’s pocketbook.

3] “I don’t know why they’re not coming here.” 

This was in reference to Holland being rebuffed by every available free-agent defenseman in the summer of 2014.

Just two years after Ryan Suter decided to play in Minnesota over Detroit, leading to the “Great Panic of 2012.” Or better known as the #2 seed in the “Signings” bracket.

4] “This is a Men’s League/Kids Aren’t the Answer.”

This statement was made the season that Gustav Nyquist wasn’t called up until Thanksgiving and STILL scored 28 goals that year.

Furthermore, it was made at a time when the league had NEVER been younger because every GM in the league figured out you needed quality young talent to augment the balance of your expensive veteran roster.

5] “I’m Kicking Tires.”

This is a perennial ditty at the NHL draft when there is speculation that Holland will make a trade ….. and then never does.

6] ‘Injured Player X Coming Back Is Like Our Trade Deadline Move’

There were many years at the end of Datsyuk and Zetterberg’s prime (and before the Cole and Legwand disasters) where a blockbuster deadline trade might have put the team over the top.

Instead, Holland would point to whatever injured player would be returning in March and state that that player will be “our trade deadline acquisition.”

7] “What If A Tank Doesn’t Work?”

I don’t know, you could go eight seasons and only win one playoff series? Has this guy left for Seattle, Vancouver or Edmonton yet?

8] “We Like Our Team.”

Oh, you’re the one.

The Signings 

1] The Loyalty Re-Signings (#8, #43, #52, #55, #65, etc.)

If we wanted to expand this tournament to 64 seeds we easily could have just split all these deals out, as they are egregious on their own.

Lumping them into one gives you the 22.1m cap hit that Helm, Abdelkader, Kronwall, Ericsson, and Dekeyser have combined for next season. That is almost 4.5 million per player for five guys who wouldn’t be core players on any contender.

Not one of these guys could crack the top nine forwards or top four d-men on a team trying to win the Cup and yet they are taking up more than a quarter (!!!!!!) of next year’s projected cap.

Abdelkader and Helm actually had some trade value in their UFA years heading into the deadline yet the Wings held on and extended them in moves that were widely derided at the time.

Hockey luminary Ryan Lambert had this to say about Helm’s deal

Darren Helm to Detroit
Horrible contract. Don’t like the term or the money. Speed is a great thing to have, but separate this guy from Datsyuk and he’s not even a 30-point player or a possession driver. This contract is almost as bad as Abdelkader’s.”

The trio of DeKeyser, Kronwall, and Ericsson are the anchors (in more ways than one) of one of the NHL’s worst defenses (somehow there are a couple of teams with less talent).

You can make an argument that the Wings have a credible forward corps for the 2017-18 season but the D is holding them back. These vet deals are just devastating to the team and its future as Joe HickettsVili Saarjarvi, and Filip Hronek languish in the AHL while waiting for these deals to expire.

These five guys have crippled the Wings maneuverability within the salary cap for the near future and like the delicious burger chain where you get peanuts while your order is prepared  …… these Five Guys will give us peanuts while we wait for their deals to run out.

2] The Class of 2012

We’ll get to the signings momentarily, but first, a little backstory.

Nick Lidstrom had just retired. Ya lost out on Ryan Suter and Zach Parise. It seemed likely there would not be a full 82-game season because of labor strife. What better time to strip away some pieces and start retooling? Filppula was entering the final season of his very affordable five-year deal and it was clear he had priced himself out of Detroit. Tough decisions loomed.

Well, not really.

Niklas Kronwall inked his seven-year deal and we were off and running.  Oft-injured Carlo Colaiacovo signed a two-year deal.

Holland then let Hudler walk and gave THREE years to Mikael Samuelsson, who was openly mocked by the head coach for his strange, recurring injuries.

The icing on the cake was THREE years for Jordin Tootoo. It’s not even worth listing any stats associated with these transactions. Colaiacovo and Tootoo would eventually take an even larger bite out of the Ilitch family inheritance pie when they were bought out by Holland.

Danny DeKeyser signed as a college free-agent late in the season and immediately became one of their top defenseman. Think about that for a second. The Wings lost Lidstrom, Brian Rafalski & Brad Stuart in a 12-month span. I never thought I’d see a more disgusting six-man defensive unit than what I saw that season.

Yet five plus years later and it’s exponentially worse.

And if you think any of this is hindsight, here is my article from July 8, 2012 regarding these signings.

3] The Uwe Krupp Signing

Probably the single worst free-agent signing in Detroit sports history. In the wake of the horrific limousine accident that severely debilitated Vladimir Konstantinov and prematurely ended #16’s career, Holland was desperate to sign a physical defenseman.

He landed on former Colorado nemesis Uwe Krupp.

I will let you Sports Illustrated explain how that went …

Yep, Krupp was too banged up to play hockey but was seemingly preparing for the Iditarod while rehabbing. In all, Krupp played 30 games in Detroit and tallied six points.

That equaled out to $2.7 million per point.

And you think the worst thing the Wings encountered with an Avalanche player was Kris Draper’s face getting rearranged.

4] The Pavel Datsyuk Front-loaded Contract

I’ve already written 3,000 words on Holland incentivizing Datsyuk to retire by front-loading his contract when he knew the future Hall of Famer had eyes on returning to Russia before the deal was up.

So read this because it’s too depressing for me to rehash again.

To summarize, Datsyuk inked a three-year extension and, one week into that contract, told Holland he wanted to be closer to his daughter in the motherland.

Datsyuk agreed to stick it out for a couple more years and then left Holland holding the bag, causing the Chychrun/Cholowski/Nielsen debacle.

5] The Frans Nielsen Signing

Where do we start? The Wings threw a six-year deal at a 32-year-old middle six center. As if they hadn’t learned from the Stephen Weiss debacle just a few years prior, the Wings landed someone comparatively older, worse, and more expensive than Weiss.

Signing a 32-year-old to a six year deal only makes sense in limited cases, and dumping Jakob Chychrun for the right to do so is emphatically not one of those cases.

Nielsen is a nice player, in a lot of ways his production and skill set compare to a poor man’s Henrik Zetterberg, and that is a compliment. He’s had a very good NHL career and was beloved on the Islanders, who struggled once he left until Matt Barzal was ready.

Players historically fall off a cliff production-wise in their early- to mid- thirties and signing a 32-year-old center is just asking to have that happen. Unsurprisingly, we are in the midst of Nielsen’s free fall into Bad Contract Land as he is at less than 0.3 points per game this season, his worst total of his career. It doesn’t seem like it will get better since aging curves head downward — something Holland should have considered at the time.

Consider this – if the Wings had traded the Evgeny Svechnikov pick, moved up a few spots to take Barzal and the following year just eaten the last season of Datsyuk’s deal and taken Chychrun, they would be in an infinitely better spot at about THREE million less than Nielsen’s contract alone.

In a couple of weeks Barzal will pass Nielsen’s career high in points.

Let that sink in.

Obviously Holland is allergic to trading up in the draft, though.

Just ask Casey Mittelstadt.

Who has been running this team’s draft lately anyhow?

A dart board?

6] The Derian Hatcher Signing

Coming off a four-game sweep at the hands of the Anaheim Ducks — a series where the Wings only gave up 10 goals and scored SIX — it was clear what needed to be done. What? Fix the defense?

“Let me give you a history lesson.” Everyone in the hockey world knew a work stoppage was coming. Teams started operating under the assumption that a salary cap was inevitable. Holland flipped those people the bird and proceeded to extend Darren McCarty, sign Ray Whitney, let a guy named Fedorov walk, and pay huge dough to the big, bruising D-Man DET fans (the dumb ones) had coveted for years.

Hatcher battled injuries during his only year wearing the Winged Wheel. He appeared in just 15 regular season games, tallying FOUR points. He was bought out within seconds of the compliance window opening. Whitney and McCarty suffered the same fate.

Hatcher will be forever remembered for skating into a puddle of wet cement during Game 6 of the 2004 playoffs. This clip is NSFW. I can’t take my eyes off him. He was Jonathan Ericsson, before Jonathan Ericsson.

Seriously, that might be the worst shift in NHL history.

7] The Stephen Weiss Signing

Although Weiss was injured in his last season with the Panthers, his prior five seasons of his bridge deal with Florida were all over 40 points and twice over 60 (a total Johan Franzen never hit).

He was a borderline elite player and the Wings were desperately in need of a quality middle six center after letting Filppula walk for nothing.

Weiss’ deal made sense on its face but the former #4 overall pick had hernia surgery just 26 games into his first season and Detroit fans know from Justin Verlander and Miguel Cabrera how long that recovery is.

Apparently the Wings didn’t know the recovery times and rushed him back not once, but twice. Weiss was never the same and was bought out just two seasons into his five-year deal and has not played since.

While the signing was defensible at the the time, there are some real questions about the handing of Weiss’s situation by the medical staff. Amusingly enough, Wings fans now get to watch from afar as Mike Babcock gets to passive aggressively pressure an injured Auston Matthews back into the lineup.

There are risks in signing an older UFA, as Weiss was 30 and not 27 at the time of the deal. Injuries become more common as players age and this was a situation where the Wings got a little unlucky, although they might have been ambitious signing someone as old as Weiss to that kind of deal.

Almost all of the critiques of Holland’s moves have occurred in real time. This is the exception to the rule and involves a lot of hindsight.

8] The Henrik Zetterberg Poison Pill Contract

Honestly, this isn’t that bad as poison pill contracts were commonplace in the NHL between lockouts. There were seven of these deals signed and teams are putting these stars on LTIR to save the pain of the cap recapture penalty once they hit the point in the contract where it’s no longer worth playing financially since the deals are all heavily front-loaded.

This is the last season of Zetterberg receiving the front-loaded portion of his deal. Next year his salary drops from 7 million to 3.5 million and the remaining two years after that are 1 million each. Its likely this year or next will be his last season.

The problem is that the deal has handcuffed the Wings into keeping Zetterberg happy so he doesn’t retire early and hit the team with a nasty recapture penalty in 2019-2021.

The penalty is the cap hit minus the actual salary. In this case it would be 5.6 million. Because folks like Holland tried to circumvent the spirt of the salary cap, it would appear the Wings are going to artificially have their budget reduced by seven percent for at least two seasons.

The tangible damage from this deal is yet to be determined as Zetterberg is still playing quite effectively, but the intangible damage, i.e. the Swedish Mafia, has undermined the middle of this decade for the Wings.

Maybe there is a light at the end of this tunnel of despair leading to one more Swede — Rasmus Dahlin? A man can dream.

So there you have it. The 32-seed tournament of the worst moves during Ken Holland’s tenure in Detroit

Voting will start immediately. If you haven’t already washed this article down with a glass of Clorox Bleach.

(You can follow Moss on Twitter @JeffMossDSR. You can discuss this article on Facebook by clicking here. You can also go fuck yourself if you’d like. Totally up to you. Topher Ryan and Ant C. also heavily assisted with the bracket and preview.)