Chicago Blackhawks 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 The book is still available on Amazon, though some of the stats on active contracts are now out of date.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.

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Stan Bowman’s legacy as a builder of champions (and a piece of shit) will be firmly entrenched in hockey lore for many years to come after winning 3 Stanley Cups and constructing a dynasty (the foundation of which was laid by Dale Tallon). My policy has always been that contracts which win a championship cannot be considered “bad”, unless that player barely saw the ice in the playoffs. For this reason, constructing the Blackhawks worst contracts list was…complicated.
 
Some contenders, like Brian Campbell and Brent Sopel had to be eliminated on the basis of having produced a championship, but you also won’t find their names on the Blackhawks crowded best contracts list.
 
 
1. Brent Seabrook
 

Signed By:	Stan Bowman		Position:	D
Date:	2015-09-26		Age July 1st:	31
Term:	8 years		Playoff GP:	4
Total Money:	$55M		Playoff PTS:	0
Cap Hit:	$6.9M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	57.1	270	97	472
Per 82 GP	7.1	82	29	143	20.1

“You can’t just go pick up a Brent Seabrook. If you don’t have someone like that, to be the performer that he is on the ice as well as the leader he is off the ice, if you don’t have Brent, you’re looking for the exact same player. We know what he’s all about”

– Stan Bowman

Brent Seabrook was a warrior who helped the franchise win 3 Stanley Cups. It’s defensible why Stan Bowman felt this reward was necessary, but giving an 8-year deal to a 31-year-old with all those hard miles on his odometer is bad asset management. Stan should have made Seabrook’s previous contract his last and gone full-term on that treaty instead of 5-years.
 
Brent was a decent player in season one when he scored 39 PTS, but the depreciation kicked in the following campaign. By year three his ice time dropped under 20 minutes per game and he started becoming a healthy scratch. In year four he suffered a serious injury to his hip, requiring multiple surgeries. The best-case scenario for the organization was Brent finishing the rest of the contract on “Robidas Island”.
 
 
2. Nikolai Khabibulin
 

Signed By:	Dale Tallon		Position:	G
Date:	2005-08-05		Age July 1st:	32
Term:	4 years		Playoff Wins:	8
Total Money:	$27M		Playoff SV%:	0.898
Cap Hit:	$6.75M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	12.0	202	90	2.81	0.904

"I know our fans have gone through some difficult times, but we said that we would remain flexible and give ourselves a chance to improve our team under the new rules governing the NHL with a new Collective Bargaining Agreement. We planned ahead with this day in mind and we are extremely happy that we were able to achieve some of our goals."

– Dale Tallon

Nikolai Khabibulin was the Stanley Cup winning starting goaltender for the 2004 Tampa Bay Lightning and one of the most prized commodities available on the open market following the 2005 lockout. The Russian chose Chicago, who made him one of the highest paid players in the league. His year one salary is equivalent to a $14.3M cap hit in 2022. At age 32, he was only able to procure a 4-year term, and lucky for Blackhawk fans it wasn’t any longer.
 
Year one was an immediate disaster, with Nikolai recording an abysmal .886 SV% in 50 GP. The good news, that terrible performance helped the Hawks get the 3rd overall pick in the draft which became Jonathan Toews. In year two Nikolai was slightly better, but the team was even worse. Ultimately their goaltender helped them tank another season and draft Patrick Kane.
 
As bad as this contract was, it did have a happy ending for Hawks fans, none of whom would ever consider getting into a time machine to undo this transaction. If they had signed a good goalie here, Toews and Kane might never have joined the team. Do the 3 Stanley Cups even happen without Saint Nikolai? Once they got this contract off the books in July 2009, the following season resulted in a championship.
 
 
3. Cristobal Huet
 

Signed By:	Dale Tallon		Position:	G
Date:	2008-07-01		Age July 1st:	32
Term:	4 years		Playoff Wins:	1
Total Money:	$22.5M		Playoff SV%:	0.914
Cap Hit:	$5.6M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	7.8	89	46	2.51	0.902

"We have created a buzz here in this market – we're starting to sell more and more tickets, more and more sponsorships. We decided that we'd try and make an impact today to continue that momentum."

– Dale Tallon

Cristobal Huet had logged 3 NHL seasons mostly as a quality back-up before 2008, when he set a new career high with 52 games played and a .920 SV%. Many prognosticators concurred that the French goalie was ready to step into a primetime role, and Dale Tallon agreed. Huet signed with the Blackhawks on the same day as Brian Campbell, and was brought in to challenge a struggling Nikolai Khabibulin for the starting job. In year one Huet played in half Chicago’s games, providing league average goaltending, but losing the starting job to Khabibulin in the playoffs.
 
Year two was where this investment took a sharp downward turn. Huet was asked to take a greater role with Khabibulin’s deal expiring, but Cristobal was not equal to the task, posting an .895 SV% in 48 GP.  Antti Niemi supplanted him as the primary goaltender in the playoffs, winning the Stanley Cup. Generally, Cup winners are excluded from my worst contract lists, except if their contribution to glory was minimal. Huet played one period that whole playoffs. Under enormous salary cap pressure that summer, Stan Bowman found a loophole that allowed the team to loan him to Europe to save money against the cap (but he still collected all his dough).
 
 
4. Seth Jones
 

Signed By:	Stan Bowman		Position:	D
Date:	2021-07-23		Age July 1st:	27
Term:	8 years		Playoff GP:	0
Total Money:	$76M		Playoff PTS:	0
Cap Hit:	$9.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	76.0	0	0	0
Per 82 GP	9.5	0	0	0	0

"I think it changes the complexion of our defense in particular, but our team in general.”

-Stan Bowman

It’s not common practice for me to declare a contract awful at the beginning of the term, as I’ll often give the player a chance to earn his money before making an official declaration of badness. I’m making an exception for Jones, who qualified for my 2022 NHL worst contracts list, and solicited many votes in the polling. 

It’s also never a good sign when a General Manager gets fired not long after a big contract is signed (like Peter Chiarelli and Mikko Koskinen). It’s even worse when a team’s effectiveness collapses after a major acquisition and begin tearing down their roster to tank and rebuild. Chicago is now in a position to suck for Seth Jones prime years, and the contract is virtually untradeable at that price point.
 
 
5. Jonathan Toews
 

Signed By:	Stan Bowman		Position:	F
Date:	2014-07-09		Age July 1st:	27
Term:	8 years		Playoff GP:	16
Total Money:	$84M		Playoff PTS:	10
Cap Hit:	$10.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	88.8	449	346	1121
Per 82 GP	11.1	82	63	205	19.6

“There's nothing we want more as players than to continue to win Stanley Cups for the best hockey fans on the planet.”

– Jonathan Toews

Jonathan Toews certainly was not a bad player on this contract (aside from one dismal campaign), but his annual cap hit was at least $3M too high. Being overpaid does not always equate to a bad investment and if the salary cap were abolished, 32 General Managers would want this Toews deal. Where this contract was problematic was trying to build the rest of the team with the remaining cap space, when Kane and Seabrook were also collecting big pay cheques. 
 
The Blackhawks have enjoyed a dynasty under the Toews regime, but also have not won a playoff series since this deal officially kicked in. Stan Bowman was able to build championship rosters around Toews and Kane’s previous pacts, but never the same after this.
 
 
6. Cam Barker
 

Signed By:	Dale Tallon		Position:	D
Date:	2009-07-06		Age July 1st:	23
Term:	3 years		Playoff GP:	0
Total Money:	$9.25M		Playoff PTS:	0
Cap Hit:	$3.08M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	12.7	122	26	149
Per 82 GP	4.2	82	17	100	15.9

“You’re not going to walk in there in the dead of night and steal a guy like Cam Barker. You’re going to have to give up something that hurts.”

- Wild Asst GM Tom Thompson

Cam Barker enjoyed a breakout season in 2009, scoring 40 PTS in 68 GP, earning himself an appropriately priced bridge deal for a 40-point campaign. It only took 51 games the following season for Bowman to realize that he might have made a mistake, shipping Barker to the Minnesota Wild for Nick Leddy and Kim Johnsson (in a trade that Wild fans still lament to this day).
 
Cam played 71 games for the Wild before they bought out the remaining year. The former 3rd overall draft pick would never again come close to 40 PTS in a season, playing only 39 more NHL games before crossing the Atlantic to play the rest of his pro career in Europe.
 
 
7. Adrian Aucoin
 

Signed By:	Dale Tallon		Position:	D
Date:	2005-08-02		Age July 1st:	31
Term:	4 years		Playoff GP:	13
Total Money:	$16M		Playoff PTS:	6
Cap Hit:	$4M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	28.3	249	91	402
Per 82 GP	7.1	82	30	132	21.6

"We weren't even close to where we wanted to be and I seemed to battle through injuries the entire time I was there. It wasn't anything easy.”

– Adrian Aucoin

Adrian Aucoin posted a career high 44 PTS with the Islanders in 2004 before the lockout, and was a very coveted commodity when the league resumed play. Aucoin landed in Chicago with Nikolai Khabibulin, which had Dale Tallon incredibly excited as though he had just won the lottery. The defenseman was later named team captain, though his tenure was anything but successful…unless you consider tanking for Toews and Kane a success.
 
Injuries did play a role in Aucoin’s problems and would have earned an injury exemption had he not also been bad when healthy.  He was brought in to provide offense and run the power play, but only produced 22 PTS in 92 GP. Prior to the 2007 draft, Aucoin’s contract was dumped on Calgary in return for a bad Andrei Zyuzin contract. After his arrival in Calgary, Aucoin’s play did improve once his healthy stabilized.
 
 
8. Steve Montador
 

Signed By:	Stan Bowman		Position:	D
Date:	2011-06-30		Age July 1st:	31
Term:	4 years		Playoff GP:	0
Total Money:	$11M		Playoff PTS:	0
Cap Hit:	$2.75M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	13.9	52	14	57
Per 82 GP	3.5	82	22	90	14.8

"The first step is to place them on waivers, which we were going to be doing, and then following that if they go unclaimed, then we're going to proceed with the buyout."

– Stan Bowman

Steve Montador had provided the Buffalo Sabres with two quality seasons of play (including a career best 26 PTS in 73 GP in 2011), prompting Stan Bowman to trade a draft pick to acquire his rights. The Hawks signed him to a 4-year extension the following day (getting a similar contract to Derek Morris and Toni Lydman a year earlier). Montador saw his ice time plunge in Chicago, dropping from 19.7 down to 14.8. He scored 14 PTS in 52 GP in year one before a concussion ended his season. Year two he played 14 games for the Rockford IceHogs before being bought out. Steve would play one more season in the KHL before retiring from pro hockey.
 
Head injuries unquestionably played a role in his downfall, and it’s with a heavy heart that I put him on this list. RIP dude. He might have qualified for an injury exemption if not for the fact that he was bad before the concussion too. There just aren’t that many bad Blackhawk contracts to choose from given my rule that Cup winners are excluded. I ran into a similar problem constructing the Pittsburgh Penguins worst list.
 
 
9. Martin Lapointe
 

Signed By:	Dale Tallon		Position:	F
Date:	2005-08-03		Age July 1st:	31
Term:	3 years		Playoff GP:	4
Total Money:	$7.2M		Playoff PTS:	0
Cap Hit:	$2.4M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	13.5	234	68	300
Per 82 GP	4.5	82	24	105	12.9

"He wanted to come to the Blackhawks and is very excited about playing in Chicago. He's not afraid to go to the front of the net. He is the type of player who fits into the style we want to play."

– Dale Tallon

Martin Lapointe scored a career high 57 PTS for the Red Wings in 2001, earning himself a pricey deal from the Boston Bruins that is among the biggest free agent busts in Bruins franchise history. He had declined all the way down to 25 PTS in 75 GP in 2004 before becoming a free agent after the lockout.
 
Marty’s years of deterioration with the Bruins did not seem to be of concern to Dale Tallon, who offered the 32-year-old a very generous bounty to lure him to Chicago. Marty played a significant role helping the team acquire Toews and Kane, so in that sense this could be considered a success. He was traded away at the end for a 6th round pick that became Ben Smith.
 
 
10. Marcus Kruger
 

Signed By:	Stan Bowman		Position:	F
Date:	2016-03-08		Age July 1st:	26
Term:	3 years		Playoff GP:	4
Total Money:	$9.25M		Playoff PTS:	1
Cap Hit:	$3.08M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	10.1	192	35	187
Per 82 GP	3.4	82	15	80	11.8

“His work ethic, reliability and strength as a two-way player made him a valuable member of the organization. We wish him the best with Vegas.”

– Stan Bowman

Marcus Kruger played an important depth role while helping the Blackhawks win 2 Stanley Cups. They rewarded him with a generous extension at age 26 after the center scored just 4 PTS in 41 GP in 2016, a stat line that warrants a salary under $1M. Kruger did bounce back and play much better in year one of this deal, but still fell short of earning his salary.
 
Bowman decided to ship him off to Vegas that summer, and the Golden Knights then flipped him to Carolina for a 5th round draft pick 2 weeks later. Kruger showed a significant regression in Carolina, eventually getting demoted to their farm team. That summer the Hurricanes dumped him on the Arizona Coyotes, who then shipped him back to Chicago 2 months later in the Marian Hossa trade. Kruger only averaged 11.8 minutes of ice time over these 3 seasons with 4 different teams.
 
 
11. Martin Havlat
 

Signed By:	Dale Tallon		Position:	F
Date:	2006-07-09		Age July 1st:	25
Term:	3 years		Playoff GP:	16
Total Money:	$18M		Playoff PTS:	15
Cap Hit:	$6M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	29.8	172	161	512
Per 82 GP	9.9	82	77	244	18.9

"He is 25 years old and has averaged about a point per game. His numbers have improved every season, and he definitely will help our goal scoring."

– Dale Tallon

Martin Havlat only played 18 games in 2006 because of a major shoulder injury, but he did return in time for the playoffs where he contributed 13 PTS in 10 GP. Havlat’s agent was threatening to only sign a 1-year contract with Ottawa so his client could test unrestricted free agency. That prompted the team to turn around and trade him to Chicago for a slew of prospects and a 2nd round draft pick. Tallon enticed him to sign a 3-year deal and forfeit some UFA status in return for a very high salary (equivalent to $11.1M in 2020).
 
Marty wasn’t exactly terrible in Chicago, just often injured and very over-priced. His 3rd year was certainly a success, scoring 77 PTS in 81 GP, including another 15 PTS in 16 playoff GP. Once he finally did test the UFA market, Havlat left the Blackhawks for greener pastures in Minnesota, which you can read about on the Wild worst contracts list.
 
 
12. Artem Anisimov
 

Signed By:	Stan Bowman		Position:	F
Date:	2015-07-01		Age July 1st:	28
Term:	5 years		Playoff GP:	4
Total Money:	$22.75M		Playoff PTS:	0
Cap Hit:	$4.55M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	24.1	282	142	494
Per 82 GP	4.8	82	41	144	16.1

"They play the game so well. The past six years, three Stanley Cups, it's very good. I'm really excited."

– Artem Anisimov

Artem Anisimov originally arrived in Chicago as part of the trade that shipped Brandon Saad off to Columbus, and Stan Bowman signed the Russian to an extension the next day, before he ever played a game in a Blackhawks jersey. Initially Anisimov was a success, finding chemistry with Patrick Kane and Artemi Panarin, whom he played with almost exclusively for his first 2 years in Chicago.
 
Once Panarin was shipped out of town, Anisimov’s scoring rate dropped from 58 PTS per 82 GP down to 35. The magic had vanished. As he depreciated into overpaid status beyond his 30th birthday, the Hawks could no longer afford to keep him around, trading the center to Ottawa for another overpaid (but slightly less expensive) Zack Smith contract. Artem’s ice time and production dropped even further in Ottawa.
 
 
13. Brandon Manning
 

Signed By:	Stan Bowman		Position:	D
Date:	2018-07-01		Age July 1st:	28
Term:	2 years		Playoff GP:	0
Total Money:	$4.5M		Playoff PTS:	0
Cap Hit:	$2.25M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	4.6	48	5	41
Per 82 GP	2.3	82	9	70	14.1

"He has a style that's a bit different. He has some physicality to his game, coming into his own. He's 28 but his last season was his best. One of those later bloomers"

– Stan Bowman

Brandon Manning had never played more than 50 NHL games in a season until age 25 with the Philadelphia Flyers. Stan Bowman decided to roll the dice on Manning as an unrestricted free agent on July 1st 2018, after the defenseman had just scored 19 PTS in 65 GP while averaging 18 minutes per game with the Flyers.  That all took a sharp nosedive upon arrival in Chicago, prompting Bowman to ship him to Edmonton for Drake Caggiula after just 27 games.
 
Manning has played more games for the Bakersfield Condors than the Edmonton Oilers, and was one of the moves that cost Peter Chiarelli his job. At best, Manning was worth the league minimum to have on a taxi squad. He was suspended in the AHL for dropping a racial slur.
 
 
14. Brandon Bollig
 

Signed By:	Stan Bowman		Position:	F
Date:	2014-03-03		Age July 1st:	27
Term:	3 years		Playoff GP:	11
Total Money:	$3.75M		Playoff PTS:	2
Cap Hit:	$1.25M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	4.4	116	9	123
Per 82 GP	1.5	82	6	87	8.9

“We take a great amount of pride in having watched Brandon come up through our system and become a big part of our lineup on a daily basis… We are pleased to be able to come to this agreement with him, ensuring that he will remain a part of our organization. We look forward to seeing his continued development with the Blackhawks.”

– Stan Bowman

Stan Bowman signed Brandon Bollig to a 3-year extension in March 2014 during his first full season of NHL duty, playing mostly a 4th line winger role. Bollig was set to become an unrestricted free agent and had to be paid accordingly, even if the price was expensive for an inexperienced 4th line grinder.
 
Unfortunately for Bollig, he would not get to hoist the Stanley Cup with his teammates 15 months later because Bowman traded him to Calgary for a 3rd round pick at the 2014 draft. Bollig averaged under 10 minutes per game with the Flames before earning himself a full-time demotion to the AHL in year three. He never played in the NHL again.
 
 
15. Kyle Calder
 

Signed By:	Dale Tallon		Position:	F
Date:	2006-07-27		Age July 1st:	27
Term:	1 years		Playoff GP:	13
Total Money:	$2.95M		Playoff PTS:	1
Cap Hit:	$2.95M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	5.5	78	35	130
Per 82 GP	5.5	82	37	137	15.5

"Calder is a player who we have coveted for a long time. He can score; he can kill penalties; he can play on any of our top three lines. He is a left wing player somewhat similar to what Michal was for us as a center iceman.”

– Bobby Clarke

Kyle Calder generated a career best 59 PTS in 2005/06 at age 26, prompting an arbitrator to award him the 2020 equivalent of $5.5M. Dale Tallon accepted the arbitrator’s ruling, but decided to trade him to Philadelphia a few days later for Michal Handzus. Kyle generated just 21 PTS in 59 GP in Philly before they decided to trade him back to Chicago Lasse Kukkonen and a 3rd round draft pick. Tallon then immediately flipped him to the Red Wings for Jason Williams.
 
This disappointing season proved to be more than just a blip in Calder’s career, it was actually the beginning of the end. He did get another multi-million dollar deal that you can read about on the LA Kings worst contracts list. He was out of the league 3 years later.