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.
Looking at their bad contract report card below with their league rank, this list ranked much lower in playoff games than their best contract list because nobody who won a Cup with Chicago is on this. They whiffed pretty hard on Seabrook and Toews last deals, among others as their average rank is high relative to my difficulty building it (at least the initial version).
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 (with a few exceptions). The book is still available on Amazon, though some of the stats on active contracts are now out of date.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. One thing you won't find here are entry level contracts because they all come from the same cookie cutter and require less skill at the negotiating table.
Updated June 23, 2024: Adjusted for $88M cap and added Nick Foligno. Seth Jones was moved down 1 spot.
1. Brent Seabrook
Adjusted Cap Hit: $60.9M, $7.6M (avg)
Value Returned: $17.9M, $2.2M (avg)
% Earned: 29%
“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”
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
Adjusted Cap Hit: $50.9M, $12.7M (avg)
Value Returned: $15.0M, $3.7M (avg)
% Earned: 29%
"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."
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
Adjusted Cap Hit: $33.9M, $8.5M (avg)
Value Returned: $7.1M, $1.8M (avg)
% Earned: 21%
"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."
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. Jonathan Toews
Adjusted Cap Hit: $94.8M, $11.9M (avg)
Value Returned: $50.4M, $6.3M (avg)
% Earned: 53%
“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 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.
5. Seth Jones
Adjusted Cap Hit: $77.1M, $9.6M (avg)
Value Returned: $51.1M, $6.4M (avg)
% Earned: 66%
"I think it changes the complexion of our defense in particular, but our team in general.”
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.
6. Cam Barker
Adjusted Cap Hit: $13.6M, $4.5M (avg)
Value Returned: $3.0M, $1.0M (avg)
% Earned: 22%
“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.”
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
Adjusted Cap Hit: $30.0M, $7.5M (avg)
Value Returned: $17.3M, $4.3M (avg)
% Earned: 58%
"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 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
Adjusted Cap Hit: $15.0M, $3.8M (avg)
Value Returned: $3.3M, $0.8M (avg)
% Earned: 22%
"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."
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
Adjusted Cap Hit: $14.1M, $4.7M (avg)
Value Returned: $4.8M, $1.6M (avg)
% Earned: 34%
"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."
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
Adjusted Cap Hit: $10.9M, $3.6M (avg)
Value Returned: $2.6M, $0.9M (avg)
% Earned: 24%
“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.”
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 Salt Lake City 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
Adjusted Cap Hit: $31.8M, $10.6M (avg)
Value Returned: $19.4M, $6.5M (avg)
% Earned: 61%
"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."
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
Adjusted Cap Hit: $25.8M, $5.2M (avg)
Value Returned: $15.0M, $3.0M (avg)
% Earned: 58%
"They play the game so well. The past six years, three Stanley Cups, it's very good. I'm really excited."
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. Nick Foligno
Adjusted Cap Hit: $9.0M, $4.5M (avg)
Value Returned: $3.2M, $1.6M (avg)
% Earned: 36%
The Chicago Blackhawks signed Nick Foligno and Corey Perry to inflated 1-year contracts because they had cap space to burn and wanted veteran influences around Connor Bedard. Perry’s deal was terminated after allegations of improper relations with Bedard’s mom (very likely completely fabricated by internet conspiracy theorists), whereas Foligno stood-up for Connor after sustaining a broken jaw, fighting the assailant. They signed him to a new 2-year deal at a similar price tag not long afterwards, which is still an overpayment. Mentorship is not a stat in my spreadsheet, but it tends to get cited far more often on bad contracts than good. They’re going to pay him roughly triple what he’s worth, it would seem so he can drop the gloves if anyone assails the golden boy.
PS: I’d love to share my idea for a parody music video of “Stacey’s Mom” called “Connor’s Mom” performed by a Corey Perry look-a-like, but that could get me sued.
14. Connor Murphy
Adjusted Cap Hit: $18.1M, $4.5M (avg)
Value Returned: $8.9M, $2.2M (avg)
% Earned: 49%
The Chicago Blackhawks traded one of their Stanley Cup warriors Niklas Hjalmarsson to the Arizona Salt Lake City Coyotes to acquire the younger and slightly cheaper Connor Murphy. The youth movement brought a similar type of player, who liked hitting and was used more frequently in defensive situations. He was a decent enough defender, but they are paying him a premium for that service, because the offensive side of his game was nowhere near that paygrade. If we’re going just by points and ice time, Murphy was getting paid double what he deserves.
15. Brandon Manning
Adjusted Cap Hit: $5.0M, $2.5M (avg)
Value Returned: $1.6M, $0.8M (avg)
% Earned: 32%
"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"
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.
16. Brandon Bollig
Adjusted Cap Hit: $4.9M, $1.6M (avg)
Value Returned: $2.3M, $0.8M (avg)
% Earned: 48%
“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 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.
17. Kyle Calder
Adjusted Cap Hit: $5.8M, $5.8M (avg)
Value Returned: $3.1M, $3.1M (avg)
% Earned: 54%
"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.”
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.
18. Ben Smith
Adjusted Cap Hit: $3.9M, $2.0M (avg)
Value Returned: $1.7M, $0.8M (avg)
% Earned: 43%
"Being a multitasker is a great tribute to certain guys. You get more quality ice time, you get more ice time, you have a longer career because you have more opportunities. He’s done a nice job."
Ben Smith scored 26 PTS in 75 GP during his first full season of NHL duty in 2014, plus an additional 6 PTS in 19 playoff GP, earning himself this 2-year bridge to unrestricted free agency at a fair price considering the stat line. Unfortunately for Ben Smith, he would not score 26 PTS in the rest of his NHL career combined.
The winger/center would only play 61 more games for the Blackhawks before getting traded to San Jose for Andrew Desjardins. The Sharks later demoted him to the AHL before dumping the remainder of the pact on the Toronto Maple Leafs with Alex Stalock and a 3rd round draft pick for Jeremy Morin and James Reimer. He only played 40 more NHL games before leaving North America to play in Germany.
19. Cam Ward
Adjusted Cap Hit: $3.4M, $3.4M (avg)
Value Returned: $1.3M, $1.3M (avg)
% Earned: 40%
Cam Ward had registered 5 consecutive seasons with a sub .900 SV% in Carolina before departing for Chicago, and wasn’t any better upon arrival in the Windy City. The Blackhawks weren’t really a contending team at this point, but were still pretending to be. Corey Crawford was getting old and trending in the wrong direction, so Ward was seen as a veteran with championship pedigree (though it had been a decade since he played a playoff game). He didn’t play any playoff games with Chicago and never played another game in the NHL after this expired.
20. Yanic Perreault
Adjusted Cap Hit: $2.6M, $2.6M (avg)
Value Returned: $0.8M, $0.8M (avg)
% Earned: 31%
Yanic Perreault was on his way out of the NHL when the Blackhawks gave him one last kick at the can at age 36. Perreault best known throughout his career as a face-off specialist with some offensive talent, but was never really able to establish himself as a top 6 forward. He played 53 games, scored 14 PTS, and never played another minute in the NHL.
Bonus Badness
21. Nikolai Khabibulin
Adjusted Cap Hit: $2.4M, $2.4M (avg)
Value Returned: $0.8M, $0.8M (avg)
% Earned: 33%
When Nikolai Khabibulin’s aforementioned terrible contract in Chicago expired, he signed another terrible deal with the Edmonton Oilers (which you can read about on their worst contract list). When the Edmonton pact expired, Chicago brought him back for one more try. At this point Nik had no gas left in the tank, and only played 4 games with Chicago, then never signed another NHL contract. This was way too much money to pay for 4 bad games (posting an .811 SV%).