Boston Bruins 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 The book is still available on Amazon, though some of the stats on active contracts are now out of date.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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Some of the team’s greatest mistakes in the salary cap era were made on the trade market, not the negotiating table (with 2 notable exceptions). Most people remember Chiarelli for the Edmonton debacle, and may forget that his Boston tenure was largely a success, winning the Stanley Cup in 2011. 

Peter’s replacement Don Sweeney has done an admirable job building a top contender in recent years, but is also responsible for the Matt Beleskey and David Backes mistakes, so there are blemishes on his record. Overpaying for toughness and grinders has been his biggest issue, but that hasn’t hindered the product on the ice given the number of stars they have playing for below market price.

 

1. Matt Belesky

Signed By:	Don Sweeney		Position:	F
Date:	2015-07-01		Age July 1st:	27
Term:	5 years		Playoff GP:	3
Total Money:	$19M		Playoff PTS:	0
Cap Hit:	$3.8M		Stanley Cups:	0

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	20.7	148	46	267
Per 82 GP	4.1	82	25	148	14.3

“We learned this the hard way a few years ago. About overspending and getting yourself in trouble. We’ve made a really fair offer and God bless him if he gets more.”

– Anaheim GM Bob Murray

Matt Belesky registered a career year at age 26 in Anaheim, scoring 22 goals (doubling his previous career high) and adding 156 hits (656 for his career) as he was scheduled to become an unrestricted free agent. Don Sweeney took the bait and made an awful mistake.

Year one of Belesky in Boston was actually quasi-decent, scoring 15 goals with 260 hits, while averaging 15.9 minutes of ice time. Most of that success came playing with Krejci, but once Belesky found himself on the Riley Nash line the following season, the goal scoring drastically dried up.

By year three Sweeney packaged him with Ryan Lindgren, Ryan Spooner, and a 1^st round draft pick in trade with the New York Rangers for Rick Nash. Boston retained 50% of Belesky’s cap hit to make that happen, and paid him millions of dollars to play for the Hartford Wolf Pack.

 

2. David Backes

Signed By:	Don Sweeney		Position:	F
Date:	2016-07-01		Age July 1st:	32
Term:	5 years		Playoff GP:	33
Total Money:	$30M		Playoff PTS:	12
Cap Hit:	$6M		Stanley Cups:	0

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	31.8	238	101	528
Per 82 GP	6.4	82	35	182	14.5

 

"I'm into winning games, so if he thinks that we're going to win more games with me playing wing, then I'm in. if he thinks that we're going to win more games with me playing center, I'm in. Whatever he thinks, I'll do it to the best of my ability."

– David Backes

David Backes accumulated over 2,100 hits (not counting playoffs) in a St. Louis Blues jersey, which should have been a red flag to General Managers when he became an unrestricted free agent on July 1st 2016. The center had already seen his scoring rate start to decline after his 30th birthday, so the warning signs were already on display before Don Sweeney placed the winning bid. This was right before Belesky had turned sour, so that sting hadn’t fully stung when Don made a similar error with a similar type of player, this time investing an even larger sum.

Once Backes arrived in Boston, the depreciation hit full bloom. In year one he had his worst season since entry level with 74 GP and 38 PTS. His ice time and point totals dropped significantly each year. As bad as this looks on Sweeney in retrospect, it wouldn’t surprise me if there were even bigger offers on the table for Backes and that he actually took less to play on a contending team. By year four Sweeney attempted to send Backes to the minors, but the proud veteran refused to report. Instead he was packaged with a first-round pick and shipped to Anaheim for Ondrej Kase.

 

3. Dennis Seidenberg

 

Signed By:	Peter Chiarelli		Position:	D
Date:	2013-10-03		Age July 1st:	32
Term:	4 years		Playoff GP:	0
Total Money:	$16M		Playoff PTS:	0
Cap Hit:	$4M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	18.3	143	26	169
Per 82 GP	4.6	82	15	97	20.9

"'D' like Dennis are hard to find. The way that he plays, it's hard to find."

– Peter Chiarelli

Peter Chiarelli gave the 32-year-old Dennis Seidenberg a 4-year extension on October 3^rd 2013 and two months later the defenseman tore both his ACL and MCL, knocking him out for the rest of the season. This is a classic example of how signing an aging veteran to a long-term extension too early can lead to an unforced error.

Once upon a time Seidenberg was a very effective player as a complement for Zdeno Chara on their drive to the Stanley Cup, but after returning from the injury was just a shell of his former self. Dennis got old fast. Chiarelli would be fired after the first year of this deal, and his replacement bought out the remaining 2 years.

4. Glen Murray

 

Signed By:	Mike O'Connell		Position:	F
Date:	2005-08-02		Age July 1st:	32
Term:	4 years		Playoff GP:	7
Total Money:	$16.6M		Playoff PTS:	0
Cap Hit:	$4.15M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	29.4	186	128	554
Per 82 GP	7.4	82	56	244	19.1

''The fact that he and Joe have a good relationship certainly doesn't hurt."

– Mike O’Connell

Glen Murray had been playing for the Boston Bruins before the 2005 lockout and decided to return to Beantown once the new CBA was signed. He had scored 92 PTS in 2003 and dropped down to 60 PTS in 2004. Mike O’Connell suggested that part of the impetus for retaining Murray was his close relationship with Joe Thornton, which he believed might entice Joe to make a long-term commitment. At 32-years-old, O’Connell was taking a risk offering Murray a 4-year term, but Glen had not experienced any injury issues over the previous 3 years in Boston.

That changed at age 32, as the winger would not play more than 64 games in a season over the course of this pact, averaging 56 PTS per 82 GP at an average adjusted cap hit of $7.3M. Where the returns to a fatal dip was year three when Murray dropped down to 30 PTS in 63 GP, prompting the team to buy out the remaining year. He was not able to get himself a new contract when he tested free agency and would eventually have ankle surgery that he claimed was originally injured while he was under contract, thus the buyout should not have been permitted. He fought the case in arbitration and lost, never playing pro hockey again.

 

5. Chris Kelly

 

Signed By:	Peter Chiarelli		Position:	F
Date:	2012-06-11		Age July 1st:	31
Term:	4 years		Playoff GP:	22
Total Money:	$12M		Playoff PTS:	3
Cap Hit:	$3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	14.8	182	57	229
Per 82 GP	3.7	82	26	103	14.8

“Kells is another guy as a centerman that had he gone to the market he would've got much more money than this"

– Peter Chiarelli

Peter Chiarelli traded a 2^nd round pick to add Chris Kelly in February 2011 and the center scored 13 PTS in the playoffs helping the team win the Stanley Cup. He followed that up with 39 PTS in 2012 to earn an almost identical contract as Tomas Kopecky one year earlier (which you can read about on the Florida Panthers worst contracts list).

Kelly never came within sight of 39 PTS again. Chiarelli’s assertion that Kelly could have “got much more money than this” on the open market at age 31 is debateable. There’s always demand for recent Stanley Cup champions, but he’s got very few comparables who made even a little bit more, so saying he’d have gotten much more is a stretch. Kelly did struggle with injuries, including a broken femur in the final year.

 

6. Dave Scatchard

 

Signed By:	Don Sweeney		Position:	D
Date:	2015-06-26		Age July 1st:	28
Term:	4 years		Playoff GP:	14
Total Money:	$11M		Playoff PTS:	3
Cap Hit:	$2.75M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	12.2	229	30	173
Per 82 GP	3.0	82	11	62	17.2

"Our team is deep at the centre position and we felt we had to take this opportunity to strengthen our defence"

– Mike O’Connell

Dave Scatchard always had limited upside as offensive player, but still managed to score a career best 27 goals and 45 PTS for the Islanders in 2003. The center only played 16 games with the Bruins before they dumped the 4-year term on Phoenix Arizona for an expiring David Tanabe contract, as O’Connell felt they needed to strengthen their defense.

In Year two Scatchard saw a significant drop in his ice time, scoring just 8 PTS in 46 GP. His season was cut short by a concussion and the Coyotes bought him out that summer. His next stop was the AHL, where he played 11 games in 2008 before sitting out the entire 2009 season to recover from post-concussion issues. Scatchard would get another shot with the Nashville Predators in 2010.

 

7. Charlie Coyle

 

Signed By:	Don Sweeney		Position:	F
Date:	2019-11-27		Age July 1st:	28
Term:	6 years		Playoff GP:	18
Total Money:	$31.5M		Playoff PTS:	9
Cap Hit:	$5.25M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	31.6	133	60	210
Per 82 GP	5.3	82	37	129	17.0

“They’re hometown guys, but they clearly want to be here. They understand the pressures of playing with the Bruins and they’re really good teammates. So for us, it was a really good fit and we’re really excited to have them.”

-Don Sweeney

The Boston Bruins inked Charlie Coyle to a 6-year extension in Nov 2019 following a season where he scored 34 PTS in 81 GP (which carries an expected free agent salary of roughly half the cap hit he received). Perhaps they thought he would get more PTS when promoted to a higher line, but that never materialized. Once the contract actually began, his scoring rate actually declined, dropping to 26 PTS per 82 GP. He bounced back to 44 PTS in year two, which still was not worth the money being paid.

 

8. Adam McQuaid

 

Signed By:	Don Sweeney		Position:	D
Date:	2015-06-26		Age July 1st:	28
Term:	4 years		Playoff GP:	14
Total Money:	$11M		Playoff PTS:	3
Cap Hit:	$2.75M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	12.2	229	30	173
Per 82 GP	3.0	82	11	62	17.2

 

“My position on Adam McQuaid is I’d love to have Adam McQuaid back with our group”

– Don Sweeney

Days before Adam McQuaid was set to become an unrestricted free agent at age 28, Don Sweeney enticed him to return to Boston with a generous 4-year deal shortly after trading fellow defenseman Dougie Hamilton to the Calgary Flames (which was harshly criticized by Bruins bloggers and some in the hockey media). In his first 6 seasons with the Bruins, McQuaid had only topped 70 games in a season once. Even if his physicality was useful, it was partially to blame for his inability to stay healthy.

Defensive blueliners who mostly provide physicality should not be paid this much money, as something in the range of $1.5M AAV would have been fair compensation. For the first 2 years of this pact, McQuaid was the same player he’d always been, but his ice time dropped significantly in year three when a leg injury cut his season short. Sweeney then pulled off an incredible trade, shipping McQuaid to the Rangers for 4th and 7th round draft picks and depth defenseman Steven Kampfer at the start of year four. When it turned out the Rangers sucked, they were able to move him to Columbus before the trade deadline for 4th and 7th round draft picks.

 

9. Marco Surm

 

Signed By:	Peter Chiarelli		Position:	F
Date:	2007-02-24		Age July 1st:	28
Term:	4 years		Playoff GP:	23
Total Money:	$14M		Playoff PTS:	7
Cap Hit:	$3.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	20.8	210	122	534
Per 82 GP	5.2	82	48	209	16.7

 

“Marco is a highly skilled and extremely fast player who scores goals and shows enthusiasm to play in traffic. He could have easily tested the free agency market, and in all likelihood would have received higher compensation, so we are thrilled that he chose to commit to Boston and our goal of building a highly competitive team for both now and for the future.”

– Peter Chiarelli

Marco Sturm had impossible expectations to fulfill in Boston as the centerpiece of their haul in the Joe Thornton trade, and the German surely gets more “hindsight hate” from Bruins fans than he deserves. Had he come to town as a free agent, he might even be remembered fondly. Injuries were partly to blame for Marco’s demise, as he had a strong year one on this deal, scoring 27 goals and 56 PTS (which looks less impressive in the shadow of Jumbo’s achievements). This came off the rails in year two when knee surgery and a concussion cut his season short.

Sturm was never the same player again. During the 2010 playoffs he tore both his ACL and MCL, delaying his start to the following season. The center was eventually moved to the LA Kings for future considerations, later claimed off waivers by Washington. After this contract expired, he signed with the Vancouver Canucks on a 1-year term. It would be his last NHL campaign before returning to Germany where he played 5 more games before retiring from professional hockey.

 

10. Jimmy Hayes

 

Signed By:	Don Sweeney		Position:	F
Date:	2015-07-06		Age July 1st:	25
Term:	3 years		Playoff GP:	0
Total Money:	$6.9M		Playoff PTS:	0
Cap Hit:	$2.3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	7.8	133	34	201
Per 82 GP	2.6	82	21	124	11.8

 

“You can’t really teach size, so being big, I have to take advantage of being as big as I am, and I’ve got to use my reach and use my skill set as well as I can and continue to develop my skill around the net to score a lot of goals”

– Jimmy Hayes

In July of 2015 the Florida Panthers pulled off a miraculous trade, moving restricted free agent Jimmy Hayes to the Boston Bruins for Reilly Smith in a cost-cutting transaction. Don Sweeney signed Hayes to a 3-year deal a few days later (very similar terms as Tommy Wingels got from the Sharks a year earlier). The 6’5 winger had just enjoyed a breakout season in Florida, scoring 19 goals and 35 PTS in 72 GP, receiving fair compensation for that stat line.

The Bruins got sandbagged, as Jimmy’s production was about to take a turn for the worse. The first year in Boston was almost decent, but still inferior when compared to his previous campaign. By year two this was a disaster, with Hayes dropping to 4th line spot duty, producing just 5 PTS in 58 GP with under 10 minutes of average ice time. Sweeney bought out the final year. Jimmy would get a 1-year contract from the Devils for the league minimum, and after 33 games with the Devils in 2018. He passed away in the summer of 2021. R.I.P.

 

11. Chuck Kobasew

 

Signed By:	Peter Chiarelli		Position:	F
Date:	2008-05-13		Age July 1st:	26
Term:	3 years		Playoff GP:	11
Total Money:	$7M		Playoff PTS:	6
Cap Hit:	$2.3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	10.0	180	73	274
Per 82 GP	3.3	82	33	125	13.5

 

"Certainly, in the short term, we hope it will spark our club. He's a proven NHL forward, has good skill and has scored 20 goals three times in his career. We're a little banged up right now."

– Minnesota Wild GM Chuck Fletcher

The Bruins traded 2/3 of their haul in the Joe Thornton trade (Stuart and Primeau) to the Calgary Flames at the 2007 trade deadline to acquire Chuck Kobasew and Andrew Ference. The Kobasew experience in Boston was entirely respectable, scoring 22 goals and 39 PTS to earn himself a very reasonable contract extension in May 2008.

Chucky posted similarly strong numbers in year one, scoring 42 PTS in 68 GP, which would turn out to be the best season of his career. The Bruins then traded him to Minnesota 7 games into year two after a slow start, in return for a 2nd round draft pick. Kobasew was a different player in Minnesota, seeing his ice time plummet, going on to score just 30 PTS in 105 GP for the Wild (a 23-point pace). He did get another multi-million dollar pay day from Colorado after this, but would be playing in Switzerland 3 years later.

 

12. Aaron Ward

 

Signed By:	Peter Chiarelli		Position:	D
Date:	2008-05-20		Age July 1st:	35
Term:	2 years		Playoff GP:	11
Total Money:	$5M		Playoff PTS:	1
Cap Hit:	$2.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	7.3	142	23	94
Per 82 GP	3.6	82	13	54	18.1

 

"He’s been a tremendous soldier here, bringing experience, bringing size and strength, bringing a stabilizing presence to our defense and, frankly, I wouldn’t have traded him anywhere else but Carolina. That’s where his home is and I really do appreciate the time and service and personality Aaron has brought to our organization."

– Peter Chiarelli

Aaron Ward won the Stanley Cup with Carolina in 2006, earning himself a 2-year deal with the New York Rangers that summer. He didn’t even last a full year in New York before the Bruins acquired him in exchange for Paul Mara. Ward’s time in Boston could be described as mediocre at best. Peter Chiarelli opted to offer the veteran defenseman a 2-year extension at a generous salary before Ward was scheduled to become an unrestricted free agent at age 32.

His ice dropped by almost 2 minutes per game in year one, as the Bruins decided to send him back to Carolina for Patrick Eaves and a 4th round draft pick in the summer. The Hurricanes flipped him to the Mighty Ducks for Justin Pogge at the trade deadline. That would be Ward’s last season in the NHL, retiring with a pair of Stanley Cup rings.

 

13. Paul Mara

 

Signed By:	Peter Chiarelli		Position:	D
Date:	2006-06-26		Age July 1st:	26
Term:	2 years		Playoff GP:	20
Total Money:	$6M		Playoff PTS:	5
Cap Hit:	$3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	10.5	139	40	180
Per 82 GP	5.3	82	24	106	20.3

 

"He plays a lot of minutes in all situations and his style of play fits today's game”

– Jeff Gorton

Paul Mara had by far the 2 best seasons of his career with the Phoenix Arizona Coyotes in 2004 and 2006, scoring 15 goals and 47 PTS after the 2005 lockout. Rather than sign him to a new contract, the Coyotes traded him to Boston for Nick Boynton and a 4th round draft pick. The Bruins signed him to a 2-year extension the same day, compensating Mara like a 40-point defenseman.

But when Paul arrived in Boston, the magic was gone, as his production dropped to half of what his pay grade demanded. The D-man would only last 56 games in Boston before getting traded to the Rangers for Aaron Ward. His first full season in New York produced 17 PTS in 61 GP while averaging under 18 minutes per game. Mara lasted 3 more years in the NHL, never again coming close to that miracle 47-point total.

 

14. Rich Peverley

 

Signed By:	Peter Chiarelli		Position:	F
Date:	2011-10-11		Age July 1st:	29
Term:	3 years		Playoff GP:	21
Total Money:	$9.75M		Playoff PTS:	2
Cap Hit:	$3.25M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	12.2	109	48	217
Per 82 GP	4.1	82	36	163	15.3

 

"Maybe we waited a little bit longer in signing some guys who are potential UFAs, but he's got speed, a good shot and he's still relatively young in the grander schemes. He's just a guy we wanted to have in our mix for the next four years.”

- Peter Chiarelli

Rich Peverley came to Boston in February 2011 when Chiarelli traded Blake Wheeler to the Atlanta Thrashers Winnipeg Jets, a steep price to pay, but it’s hard to argue with the results. Peverley contributed 12 PTS during the Bruins run to a Stanley Cup championship. The center was handsomely rewarded the following September with a 3-years extension for more than twice as much money as his previous contract.

This pact did not begin until after his 30^th birthday and when the league resumed after the 2012 lockout, Peverley’s scoring rate was cut in half. There was a substantial drop in both his offensive output and ice time, so the Bruins sent him to Dallas as part of the Tyler Seguin trade. He wasn’t much better in Dallas before suffering a cardiac episode and collapsing on the bench in 2014, never playing professional hockey again. This contract was already bad when that incident occurred, and no demerits were issued for the final season spent on IR when the insurance company picked up the bill.

 

15. Andrew Raycroft

 

Signed By:	Mike O'Connell		Position:	G
Date:	2005-09-16		Age July 1st:	25
Term:	1 year		Playoff Wins:	0
Total Money:	$1.3M		Playoff SV%:	0.000
Cap Hit:	$1.3M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	2.8	30	8	3.71	0.879

 

''I explained what he means to the team and how we treated him compared to our other young players in the past, and I think that might have helped get this deal done. We want to field the best team we can and Andrew is a big part of it. Having Andrew back in the fold just gives your team confidence.”

- Mike O’Connell

"It just didn't work out. The year didn't go the way he wanted or we wanted. I think it got to Andrew to be quite honest. I think the situation got to him, I think the trade of Joe Thornton got to him, I think a lot of things got to him."

– Jeff Gorton

 

"We got a 26-year-old goalie with a tremendous future in front of him."

– John Ferguson

Andrew Raycroft won the Calder trophy as Rookie of the Year the season before the 2005 lockout (posting a 2.05 GAA and .926 SV%), then spent the lost season playing in Finland. He held out past the start of training camp trying to extract more money, but ultimately the team had limited cap space and Raycroft had very little leverage.

We have no idea what happened to Andrew in Scandinavia, but he was never the same goalie again. Raycroft was downright terrible when he returned from Finland, posting 8 wins, 19 losses, with a 3.71 GAA and .879 SV% as Tim Thomas emerged as the Bruins best goaltender.

The good news was that he was young enough that the Toronto Maple Leafs believed his 2005/06 disaster was just a fluke and traded a young Tuukka Rask to acquire Raycroft. Rask would eventually win the Vezina trophy while Raycroft only every had 1 more season as a starting goalie. Ouch.