Detroit Red Wings 15 Worst Contracts (2005-2022)

This was originally published in my 2020 book The Definitive Guide to Salary Mismanagement, and has now been updated with new contracts. I will continue to update each team’s list every summer going forward. The rule is that only active contracts can move up or down. Expired deals cannot pass each other. Next summer it may even be expanded to top 20. The book is still available on Amazon, though some of the stats on active contracts are now out of date. You may yet find it interesting because there were detailed stat graphics that you won't find here.
 
My latest book The Hockey Economist’s Betting Prospectus is now available. It's a comprehensive commentary on the last 3 years of hockey betting, broken down by team, by category, by strategy, by season. There is plenty of useful information for bettors of all skill levels. It covers pre-pandemic, peak-pandemic, post-pandemic. What worked, what failed. Lessons learned, market trends, team-by-team analysis. What impact did the pandemic have on hockey betting? The market differences between these 3 seasons are discussed at length, and there's a lot to talk about. To read more, visit the Amazon store.
 
Enjoy! Please note: The formatting on the graphics got scrambled being copied from Excel into Google Blogger. It's among the reasons my blog is looking for a new home.

-----------------------------------

The line between the Detroit Red Wings best and worst contracts in the salary cap era has a very clearly defined boundary, the retirement of Nick Lidstrom. Most of their best deals were signed before he walked away from the game, and 100% of their worst were signed afterwards. Infact, their entire worst contracts list is squeezed into a 4-year period from his retirement in 2012 to the end of their playoff streak in 2016.
 
It’s fascinating how the retirement of Lidstrom suddenly transformed Ken Holland into a worse General Manager. Their roster struck an iceberg in May 2012, but it took 4 years for the Titanic to sink. Most of the new free agents he acquired to fill the holes failed, but several mistakes were also existing players getting re-signed to long-term extensions beyond the window. The words “we can’t keep losing players” or “we can’t afford to lose him” was the repeating justification.
 
Full disclosure, I’m a life-long Red Wings fan who still suffers residual PTSD from the Lidstrom retirement. The playoff streak was extended a few extra years beyond Saint Nick’s departure, and not because Holland orchestrated brilliant transactions, but rather the greatness of Pavel Datsyuk and Henrik Zetterberg. Once the Magic Man retired, they started a new streak of consecutive playoffs missed. Though once the playoff streak was over, Holland did make some shrewed moves to kick start the rebuild, and there haven’t been any disabilitating blunders since. Steve Yzerman did not sign any of these contracts.
 
 
1. Stephen Weiss
 

Signed By:	Ken Holland		Position:	F
Date:	2013-07-05		Age July 1st:	30
Term:	5 years		Playoff GP:	2
Total Money:	$24.5M		Playoff PTS:	0
Cap Hit:	$4.9M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	28.7	78	29	80
Per 82 GP	5.7	82	30	84	12.5

"Coming from Florida, only being in the playoffs one time, it was pretty easy decision to come play for Red Wings"

– Stephen Weiss

The Red Wings have a 1A and 1B situation atop their list of bad contracts, but my preference is to rank Stephen Weiss as the bigger blunder. There was every reason to be nervous about Weiss when he hit the UFA market at age 30. In the lockout shortened 2013 schedule the center scored only 4 PTS in 17 games before wrist surgery ended his season (hold on a second while I check my Twitter history to make sure I wasn’t jacked about this treaty when it was signed).
 
Weiss had been close to a 60-point player one year earlier, but never again regained that form. Hernia surgery in year one of the contract did not help either. This deal only lasted 2 seasons before being bought out, with Weiss averaging 30 PTS per 82 GP and only 12.5 minutes per game.
 
 
2. Justin Abdelkader
 

Signed By:	Ken Holland		Position:	F
Date:	2015-11-12		Age July 1st:	29
Term:	7 years		Playoff GP:	0
Total Money:	$29.75M		Playoff PTS:	0
Cap Hit:	$4.25M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	31.0	259	78	349
Per 82 GP	4.4	82	25	110	15.3

"We couldn't afford to lose him.”

– Ken Holland

For years Abdelkader’s primary purpose was a complimentary player for Pavel Datsyuk, who abruptly returned to the Soviet Union before this contract even started. It’s no coincidence that Abdelkader’s production suddenly plummeted, without such a dynamically talented player feeding him the puck. Buyer beware if you’re giving out 7 years of term to a 29-year-old banger who has accumulated many hard miles in their careers.
 
Over the first 4 years, Abdelkader averaged 25 PTS per 82 GP. The Wings received roughly 38 cents of value for each dollar invested. Year four saw Justin score just 3 PTS in 49 GP, playing 11.5 minutes per game, prompting Yzerman to buy out the remaining 3 years of the deal.
 
 
3. Frans Nielsen
 

Signed By:	Ken Holland		Position:	F
Date:	2016-07-01		Age July 1st:	32
Term:	6 years		Playoff GP:	0
Total Money:	$31.5M		Playoff PTS:	0
Cap Hit:	$5.25M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	33.1	319	124	526
Per 82 GP	5.5	82	32	135	15.6

“He's a 200-foot player. He can play power play, penalty kill, is good in shoot-outs. No one can replace Pavel, but we think we’ve added a legitimate No. 2 center.”

– Ken Holland

Ken Holland had a giant hole to fill in July 2016 in the wake of Pavel Datsyuk’s surprise early retirement, and needed a new 2-way center. The solution was giving $31.5M to Frans Nielsen following a 20-goal, 52-point performance. Let this be a lesson to NHL General Managers, don’t give 6-year deals to 32-year-old players, no matter how desperate you might be for a decent pivot. Perhaps Holland knew the back half was going to be painful, but was willing to do whatever it took to milk that playoff streak as long as humanly possible. By the time this deal turned bad, Zetterberg would likely be gone and the team would be rebuilding anyway.
 
Regrettably, the streak ended immediately and the Red Wings have not played a single playoff game since Nielsen was added to the roster. He was a decent player for the first 3 seasons, albeit at far too high of a price tag. This really started to turn ugly in year four, when he scored 9 PTS in 60 GP with the team finishing in dead last.
 
 
4. Jonathan Ericsson
 

Signed By:	Ken Holland		Position:	D
Date:	2013-11-27		Age July 1st:	30
Term:	6 years		Playoff GP:	12
Total Money:	$25.5M		Playoff PTS:	5
Cap Hit:	$4.25M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	28.2	355	57	343
Per 82 GP	4.7	82	13	79	18.6

“You can't keep losing players. After a while, you wake up and there's not enough players.”

– Ken Holland

When Nick Lidstrom retired, Jonathan Ericsson’s ice time jumped from 17 to 21 minutes per game as he was among those tasked with filling the void. But unlike Lidstrom, nobody ever had any illusions that Ericsson was going to be an offensive contributor in this league, or that he’d be effective in a top pairing role. The decision to extend him for 6 years past his 30th birthday was more about stopping the exodus of defensemen and keeping the playoff streak alive.
 
This might have been acceptable had it been 4 years at $2.5M, instead Holland dumped another $25M into the Lidstrom void. By the final year, Ericsson was waived and sent to the AHL. He would average 13 PTS per 82 GP over these 6 years.
 
 
5. Jimmy Howard
 

Signed By:	Ken Holland		Position:	G
Date:	2013-04-11		Age July 1st:	29
Term:	6 years		Playoff Wins:	1
Total Money:	$31.8M		Playoff SV%:	0.914
Cap Hit:	$5.3M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	6.1	282	113	2.71	0.911

“Jimmy is one of our most valuable players who is entering the prime of his career. He gives us a chance to win every night.”

– Ken Holland

Jimmy Howard was an effective goaltender during the lockout shortened 2013 season, posting a .923 SV% and helping the Wings to the 2nd round of the playoffs. He was set to become an unrestricted free agent at age 29, forcing Ken Holland to pay the UFA price. Add this to the pile of “players we can’t afford to lose”.
 
The Red Wings still considered themselves a contender, and the depth chart behind Jimmy was bleak. Petr Mrazek had still only played 2 NHL games, so the team had no certainty that he’d be able to handle a full-time load. Jonas Gustavsson was under contract for one more year, but the Monster had just posted an .879 SV% as the back-up. There were zero good UFA goalies coming available that July. Anyone who needed a goaltender would have been pursuing Howard. It was a perfect storm.
 
The Red Wings got a below average goaltender for an above average price. Howard was a very streaky goalie who often ran hot and cold, but the faucet was mostly chilly. Over these 6 years, he was only an above league average save percentage once, in an injury shortened 2017. Ken Holland did try hard to dump this contract for years after Mrazek emerged and could never find a buyer.
 
 
6. Danny DeKeyser
 

Signed By:	Ken Holland		Position:	D
Date:	2016-07-26		Age July 1st:	26
Term:	6 years		Playoff GP:	0
Total Money:	$30M		Playoff PTS:	0
Cap Hit:	$5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	31.5	313	71	321
Per 82 GP	5.3	82	19	84	20.4

"Danny is Detroit born, he's happy with his role, happy to be a Red Wing. We are happy with his play"

– Ken Holland

Danny DeKeyser was one year away from unrestricted free agency in the summer of 2016, so Ken Holland would have to pay the UFA price if he wanted the defenseman’s signature on a long-term deal. By that time, their depth on the blueline was dreadfully shallow and they really could not afford to lose one of their top minute eating D-men.
 
Danny played a lot of tough minutes against other team’s top lines, but had limited offensive upside. This was not exactly a terrible deal, initially, but injuries severely worsened towards the end. Had it been 6 years at a $3.5M cap hit. When this expired, he did not get any contract offers to play in the NHL.
 
 
7. Darren Helm
 

Signed By:	Ken Holland		Position:	F
Date:	2016-07-01		Age July 1st:	29
Term:	5 years		Playoff GP:	0
Total Money:	$19.25M		Playoff PTS:	0
Cap Hit:	$3.85M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	20.4	301	89	531
Per 82 GP	4.1	82	24	145	14.8

“As you watch the Stanley Cup playoffs it re-emphasized the importance of speed and that’s something Darren has. He’s a homegrown player, a draft pick of ours, and we’re glad to keep him because he’s becoming a bit of a leader.”

– Ken Holland

Darren Helm already had an extensive and concerning injury history when he became an unrestricted free agent on July 1st 2016 at age 29. Darren had managed to stay healthy for back-to-back seasons, and was still an effective complementary role player (peaking at 33 PTS in 2015). The center listened to offers from around the league, and decided that Ken Holland’s bid was indeed his best option (good chance that the final agreement was close to what Holland had been offering all along).
 
Helm would suffer multiple injuries in year one and was quasi-decent (though still overpaid) in year two when he potted 31 PTS and played 15.6 minutes per game; but it was a downhill slope from there. A 3-year deal around $2.5M would have been acceptable.
 
 
8. Mikael Samuelsson
 

Signed By:	Ken Holland		Position:	F
Date:	2012-07-01		Age July 1st:	35
Term:	2 years		Playoff GP:	5
Total Money:	$6M		Playoff PTS:	2
Cap Hit:	$3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	7.7	30	4	40
Per 82 GP	3.8	82	11	109	10.7

“We wanted to keep him three years ago, but the salary was beyond where we wanted to go. He can skate, play the right side on the power play.''

– Ken Holland

Mikael Samuelsson won a Stanley Cup with Detroit in 2008 and left for a big pay day in Vancouver, where the first 2 years were the best of his career, before taking a step backwards in 2012. He returned to the UFA market at age 35 where he received one of those overly generous “thanks for the memories” contracts.
 
That’s when his body started breaking down, suffering a variety of different injuries in year one. The winger followed that up with 3 PTS in 26 GP. While injuries did play a factor in his demise, Mikael also proved ineffective when healthy, scoring just 12 PTS per 82 GP, averaging under 11 minutes of ice time per game. Samuelsson played one more season in Sweden before retiring from hockey.
 
 
9. Jakub Kindl
 

Signed By:	Ken Holland		Position:	D
Date:	2013-06-28		Age July 1st:	26
Term:	4 years		Playoff GP:	6
Total Money:	$9.6M		Playoff PTS:	0
Cap Hit:	$2.4M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	11.4	184	44	251
Per 82 GP	2.9	82	20	112	16.0

“That's the way the business is now and hopefully he gets picked up and can go and play somewhere else."

– Henrik Zetterberg

Jakub Kindl was a 1st round draft pick of the Red Wings in 2005, taking the slow road to the NHL. The Czech defenseman put up good numbers in the AHL and certainly passed the eyeball test as a quick skating puck distributor. Kindl was seen to have a bright future and was an analytics darling with high corsi numbers. He produced at a 26-point pace during the lockout shortened 2013 season, earning himself a 4-year extension at a fair price given the stat line.
 
We would soon find out that the analytics were just a mirage with Jakub getting waived in year three and sent to the AHL. Holland was able to swing a trade with the Florida Panthers for a 6th round pick by eating some salary. Somebody in the Florida front office surely looked at his Corsi and decided he was a potential steal, which turned out to be a “false positive”. Kindl scored more PTS for the Panthers farm team than he did on their big league roster. Players making this kind of money aren’t supposed to still be playing in the AHL.
 
 
10. Carlo Colaiacovo
 

Signed By:	Ken Holland		Position:	D
Date:	2012-09-13		Age July 1st:	29
Term:	2 years		Playoff GP:	9
Total Money:	$5M		Playoff PTS:	1
Cap Hit:	$2.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	6.4	6	1	12
Per 82 GP	3.2	82	14	164	18.9

"I just want to be straightforward: I'm no Nick Lidstrom, but I think I'm a good complement to what they have there"

– Carlo Colaiacovo

Nick Lidstrom retired in the summer of 2012, one year after Brian Rafalski, and the team had a massive void to fill. Spoiler alert: they still have not filled that void, and have dumped a ton of bad money down that rabbit hole in the decade to follow. Among the first of those dominos to fall was Carlo Colaiacovo, who became an unrestricted free agent at age 29 after scoring 19 PTS in 64 GP for St. Louis. Carlo had gone unsigned all summer, unable to find a team willing to make a long-term commitment.
 
GMs would have been discouraged by his extensive injury history, so the defenseman settled on a 2-year offer from Detroit in the middle of September. Spoiler alert: Colaiacovo played 6 games before suffering a serious shoulder injury, prompting Holland to later buy out the final year before Carlo even had the opportunity to prove himself. His career lasted 3 more seasons after this termination, where he proved he was nothing better than a low-end replacement level player.
 
 
11. Jordin Tootoo
 

Signed By:	Ken Holland		Position:	F
Date:	2012-07-01		Age July 1st:	29
Term:	3 years		Playoff GP:	1
Total Money:	$5.7M		Playoff PTS:	0
Cap Hit:	$1.9M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	7.1	53	9	56
Per 82 GP	2.4	82	14	87	8.6

“Toots doesn’t want to be in the American League. We don’t want him to be in the American Hockey League”

– Ken Holland

Jordin Tootoo spent the first 8 years of his NHL career playing for the Nashville Predators, maxing out at 30 PTS in 2012 before becoming an unrestricted free agent at age 29.  The Preds were their division rival, and had eliminated Detroit from the playoffs a few months before Holland procured Toots autograph on a new deal. The Wings were looking to get tougher, and what better way to accomplish that goal than depriving a rival of one of their toughest bangers.
 
At least that was the theory. The experiment did not go according to plan. Year one in Detroit saw him score 8 PTS in 42 GP averaging 9.1 minutes of ice time. By year two he was an expensive addition to the Grand Rapids Griffins before being bought out. This wasn’t the end of the Tootoo train, as he played 184 more NHL games, providing decent value as a low paid 4th liner in New Jersey.
 
 
12. Petr Mrazek
 

Signed By:	Ken Holland		Position:	G
Date:	2016-07-27		Age July 1st:	24
Term:	2 years		Playoff Wins:	0
Total Money:	$8M		Playoff SV%:	0.857
Cap Hit:	$4M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	4.5	89	32	3.04	0.901

“When the wheels came off of Jimmy Howard in January and February, Petr Mrazek took the ball and ran. And when the wheels came off of Petr in the middle of February and March, Jimmy Howard took the ball and ran. We’re going to need two really good goaltenders like all teams do.”

– Ken Holland

Petr Mrazek played 54 games with 27 wins, 2.33 GAA and .921 SV% before signing this contract. That dropped down to 50 GP with 18 wins, 3.04 GAA, .901 SV% in year one. That sudden drop also coincided with the retirement of Pavel Datsyuk, when the team immediately became worse. Losing a perennial Selke nominee has to hurt a goalie.
 
Holland was able to trade Mrazek to the Philadelphia Flyers for a 3rd round pick, which could have been more had conditions been met. Mrazek was bad in Philly. The Czech gatekeeper would find redemption eventually in Carolina, which would be his next stop.
 
 
13. Kyle Quincey
 

Signed By:	Ken Holland		Position:	D
Date:	2014-07-01		Age July 1st:	28
Term:	2 years		Playoff GP:	11
Total Money:	$8.5M		Playoff PTS:	4
Cap Hit:	$4.25M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	10.0	120	29	152
Per 82 GP	5.0	82	20	104	19.6

''We pursued some right-shot defenseman and when they were off the market, we signed Quincey. The cap went up, and so did the cost of players.''

– Ken Holland

When Brian Rafalski retired and it became increasingly clear that Nick Lidstrom was leaning towards retirement too, Ken Holland traded a 1st round draft pick to the Tampa Bay Lightning to acquire Kyle Quincey to help fill that pending void. That draft pick would become future Vezina trophy winner and Stanley Cup champion Andrei Vasilevskiy. Quincey eventually signed back-to-back 2-year tickets that were very similar. I was tempted to package them together into a single 4-year contract and move it much higher up the list, but instead just ranked the worse of the two. Kyle made it all the way to July 1st as a UFA, but was retained by the Red Wings after Holland missed out on the more desirable acquisitions. I’d be fascinated to know what other offers Quincey had on the table.
 
The nicest thing that I can say about Kyle Quincey is that he ate some minutes while helping extend the playoff streak a few more seasons. His offensive contributions were negligible, but he played post-season games in all 4 years. The veteran defenseman’s next contract would be for a fraction of this price, playing 2 more years before moving on to Finland. My own opinion of Quincey’s legacy might be biased by my disdain for his skating style, which looked like he was sitting on a toilet.
 
 
14. Daniel Cleary
 

Signed By:	Ken Holland		Position:	F
Date:	2014-07-10		Age July 1st:	35
Term:	1 year		Playoff GP:	0
Total Money:	$2.5M		Playoff PTS:	0
Cap Hit:	$2.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	3.0	17	2	17
Per 82 GP	3.0	82	10	82	9.1

"Certainly two years ago when he made a decision to stay in Detroit and he's been offered three-year contracts in Winnipeg and Florida and Philadelphia, I know what he walked away from. So my management philosophy, part of it is being loyal and holding up my end of the bargain.”

– Ken Holland

When Dan Cleary become an unrestricted free agent in July 2013, he allegedly received a few generous offers from other suitors, but Ken Holland made a handshake agreement that he would eventually get paid all that money if he chose to remain with the Red Wings. Salary cap constraints meant that the promise could not be paid out all at once, instead getting parsed into future payments. Like with Quincey, I was tempted to bundle Cleary’s next 3 contracts into a single package and rank it higher up the list, but opted instead to choose the worst of the three.
 
The deal signed on July 10, 2014 had a $1.5M base salary, plus an easily attainable $1M bonus if he played 10 games. Danny played 17 games, scoring 2 PTS, and never played in the NHL again, but he did get one more $950K payment to play in Detroit Grand Rapids. Clearly Cleary was at the end of his road when the handshake agreement occurred, as Ken Holland bailed out the Philadelphia Flyers from making a huge mistake. That’s why you won’t be reading about a 3-year Dan Cleary treaty on the Flyers worst contracts list.
 
 
15. Pavel Datsyuk
 

Signed By:	Ken Holland		Position:	F
Date:	2013-06-18		Age July 1st:	35
Term:	3 years		Playoff GP:	12
Total Money:	$22.5M		Playoff PTS:	5
Cap Hit:	$7.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	26.1	129	114	346
Per 82 GP	8.7	82	72	220	19.4

“This deal ensures that Pavel will be in Detroit for the next four years”

– Ken Holland

It may be hypocritical/blasphemous of me to include this Pavel Datsyuk contract on the list, as there’s a 100% chance that I was thrilled when the Magic Man made this 3-year commitment to stay in North America. There is always risk giving term to 35+ players because their salary continues to count against the cap if they choose to retire early, but surely a legacy icon like Pavel wouldn’t have agreed to this treaty unless he really intended to play it out and would never f**k the team by returning to Russia.
 
I was wrong. That’s exactly what happened. It would put Ken Holland in the difficult position of having to dump the final year on the Phoenix Arizona Coyotes. They passed up an opportunity to draft Jakob Chychrun, moving down to take Denis Cholowski. The silver lining is that they also added a 2nd round pick in that trade that became Filip Hronek.