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 The book is still available on Amazon, though some of the stats on active contracts are now out of date.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

If you’d like to browse my other best/worst contract lists, click here. 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.
 
-----------------------------------------------------

Recruiting players to come play in San Jose is a much easier task than the challenge faced by his counterparts in Northern Canada. For years Doug Wilson avoided long-term obligations to older players, convincing his stars to take less term. From 2005 to 2015, Wilson only signed one contract over 5 years in length (to a 23-year-old Milan Michalek). Then in 2016 he inked an over-30 Brent Burns to an 8-year deal, and eventually Logan Couture, Marc Vlasic, Evander Kane, Erik Karlsson followed suit. The team had a catastrophic collapse in 2020, as the team is now boxed into a precarious situation.
 
 
1. Marc-Edouard Vlasic
 

Signed By:	Doug Wilson		Position:	D
Date:	2017-07-01		Age July 1st:	31
Term:	8 years		Playoff GP:	18
Total Money:	$56M		Playoff PTS:	8
Cap Hit:	$7M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	56.5	268	60	274
Per 82 GP	7.1	82	18	84	18.5

“We’re thrilled we could get this extension done early and ensure one of the League’s top defensemen will remain in San Jose for the long term.”

– Doug Wilson

During the Covid crisis of 2020, I posted a series of Twitter polls in a “bracket challenge” to determine the worst contract in the NHL, and Marc-Edouard Vlasic emerged victorious. After more than a decade of Doug Wilson convincing his best players to take either a discount or shorter term to stay in beautiful San Jose, Brent Burns long-term extension opened the floodgates. Doug was unable to get either a discount or a shorter term with Marc, who would have been reaching the UFA market at age 31.
 
It didn't take long for Vlasic to become a profound liability, for a few different reasons. The team’s salary cap situation eroded their depth, forcing the coach to use the aging veteran far more than he should. Edouard’s personal offensive numbers plunged, but more alarmingly, most of his teammates were demonstrably worse when Marc was on the ice (both in shot and expected goal differential). The Sharks went from Stanley Cup contender to one of the worst teams in the league in just a few months, and Ed bears significant personal responsibility.
 
At one point, Vlasic admitted that he considered risking contract termination to play for Canada in the 2018 Olympics. Perhaps more Sharks fans should have been encouraging him the leave and fulfill his patriotic duty. Hindsight is always 2020….
 
 
2. Erik Karlsson
 

Signed By:	Doug Wilson		Position:	D
Date:	2019-06-17		Age July 1st:	29
Term:	8 years		Playoff GP:	0
Total Money:	$92M		Playoff PTS:	0
Cap Hit:	$11.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	92.4	158	97	347
Per 82 GP	11.6	82	50	180	23.9

"I'm excited to continue the chase for the ultimate prize: the Stanley Cup"

- Erik Karlsson

Doug Wilson paid a hefty price to acquire Erik Karlsson from the Ottawa Senators, hoping it would be enough to push the team over the top in their pursuit of a championship. They fell short of their goal and Doug didn’t want to let the 2-time Norris Trophy winner depart in free agency. Erik was 2 weeks away from hitting the open market and was fully aware that somebody was going to meet his asking price. It’s likely that Doug’s initial bid was much smaller than $11.5M per season, but Karlsson had all the leverage. He could just say “this is what I’m going to get, take it or leave it”.
 
The risk here is that Erik had accumulated a concerning injury history and is at an elevated risk of deterioration. In the summer of 2022, Karlsson finished first place in my worst NHL contract Twitter poll series, and Erik responded with a vengeance, playing like a Norris contender. This might need to be demoted in future updates. He has me doubting this is even bad.
 
 
3. Martin Jones
 

Signed By:	Doug Wilson		Position:	G
Date:	2017-07-01		Age July 1st:	28
Term:	6 years		Playoff Wins:	10
Total Money:	$34.5M		Playoff SV%:	0.898
Cap Hit:	$5.75M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	5.8	137	68	3.04	0.896

"We're very happy we could get this extension done with Martin and feel that he is just beginning to hit his peak in terms of growth and prime playing seasons. He has proven that he is more than capable of excelling in high-pressure situations and big games, and we feel he has become one of the top goaltenders in the League.”

– Doug Wilson

Martin Jones had provided 2 consecutive seasons of mostly reliable goaltending for the Sharks (including backstopping the team to within 2 wins of the Stanley Cup in 2016), when Doug Wilson decided to give him a 6-year extension on the same day that he re-upped Vlasic. On July 1st 2017 Wilson committed $90M to Vlasic and Jones, which is in the conversation for worst day any GM has had in the salary cap era (Sather signing Drury and Gomez on the same day is probably still #1). Jones still had relatively few miles on his odometer for his age, but Doug could not foresee that Martin would hit a wall at age 28.
 
Over the first 2 years, Jones was among the worst starting goalies in the league with an .896 SV%, eventually getting supplanted as the primary starter by Aaron Dell in year two. It’s always especially painful when a deal is this bad right out of the starting blocks. Fans don’t get the opportunity to enjoy a few good years before it starts breaking bad. He did manage to win 10 playoff games in 2019 with an .898 SV% as the Sharks were able to outscore their problems. Infact that quest to maximize offense by sacrificing defense might have had something to do with Jones demise. He may have been a victim of a different problem, but even so, it was a waste of money.
 
 
4. Logan Couture
 

Signed By:	Doug Wilson		Position:	F
Date:	2018-07-01		Age July 1st:	30
Term:	8 years		Playoff GP:	0
Total Money:	$64M		Playoff PTS:	0
Cap Hit:	$8M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	64.3	182	126	439
Per 82 GP	8.0	82	57	198	18.9

“I see the guys under contract that we have. We have some very good players. Marc-Edouard Vlasic, Brent Burns, Martin Jones, Evander Kane, Joe Pavelski. Very, very good players”

– Logan Couture

Logan Couture played like a $7M player for the final 2 years of his previous contract, which did not expire until after his 30th birthday. The price tag wasn’t necessarily egregious, but there is considerable risk giving an 8-year deal to a 30-year-old player. He would have been around the same production in year one of this pact had it not been for injury, but the real regression wouldn’t come until the Covid shortened 2021 season.
 
The 2021 schedule started reasonably strong for Logan as the Sharks enjoyed some success against the weaker opponents in a weak division. But as the schedule wore on, the scoring started drying up. He would finish the season scoring at a 48-point pace, his weakest performance since he was a rookie. It’s hard to judge whether that decline was solely attributable to being on such a bad team, or due to injury, but he rebounded back to a 60-point pace in year three. He qualified for both my 2021 and 2022 Worst NHL Contracts list as voted on by my Twitter followers.
 
 
5. Paul Martin
 

Signed By:	Doug Wilson		Position:	D
Date:	2015-07-01		Age July 1st:	34
Term:	4 years		Playoff GP:	37
Total Money:	$19.4M		Playoff PTS:	6
Cap Hit:	$4.9M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	21.5	173	48	112
Per 82 GP	5.4	82	23	53	19.5

“I haven’t won a Cup yet. That was at the top of the list. Besides last year missing the playoffs, San Jose was one of the teams at the top of my list as far as being able to win. They’ve proven that they can win.”

– Paul Martin

Paul Martin played 5 seasons with Sidney Crosby and Evgeni Malkin, winning zero Stanley Cups. They won right before he got there, and won 2 more right after he departed. He signed a 4-year deal on July 1st 2015 at age 34 and was decent at times. The Sharks advanced to the Cup final in his first year, and he even made a decent offensive contribution in year two.
 
The warning sign that this was about to break bad was the declining ice time. Regardless of how you grade the first 2 seasons, year three was an absolute catastrophe. Paul only played 14 games, averaging 14 minutes of ice time, and was sent to the AHL for a chunk of the season. Wilson called him back up in the playoffs as an injury substitution and would buy out the remaining year that summer. Martin came to San Jose to win a Cup, and came within 2 wins of being disqualified from this list.
 
 
6. Mark Bell
 

Signed By:	Doug Wilson		Position:	F
Date:	2006-07-25		Age July 1st:	25
Term:	3 years		Playoff GP:	4
Total Money:	$6.5M		Playoff PTS:	0
Cap Hit:	$2.2M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	10.8	106	31	158
Per 82 GP	3.6	82	24	122	11.9

“He’s a top-6 forward. That’s the beauty of our group. We’ve got guys who can play center and wing. We can have different looks. We’re trying to get players together who can get it done in the playoffs, guys who play with an edge.”

- Doug Wilson

 

“Most folk heroes started out as criminals.”

- Reggie Dunlop

In July 2006, Doug Wilson traded Tom Preissing and Josh Hennessy to acquire Mark Bell from the Chicago Blackhawks, and signed him to a new deal 2 weeks later. Wilson paid a 40-point price but only received half of what he thought he bought. Bell dropped from 48 PTS down to 21 PTS before getting traded to Toronto in the Vesa Toskala trade (the Sharks adding 1st, 2nd, and 4th round draft picks).
 
Doug managed to turn a negative into a positive before it crashed and burned…quite literally. A DUI hit and run later that summer proved to be beginning of the end of Bell’s career. He would play more games for the Marlies than the Leafs.
 
 
7. Mikkel Boedker
 

Signed By:	Doug Wilson		Position:	F
Date:	2016-07-01		Age July 1st:	26
Term:	4 years		Playoff GP:	14
Total Money:	$16M		Playoff PTS:	8
Cap Hit:	$4M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	17.1	246	102	358
Per 82 GP	4.3	82	34	119	13.6

"I understand what he can do. He has some untapped upside that we haven't seen yet"

– Peter Deboer

Mikkel Boedker became an unrestricted free agent at age 26 after 7 seasons in the NHL, having just tied his career best 51 PTS in 2016.  Doug Wilson paid a fair price for a 50-point winger, unfortunately he that’s not what Fed Ex dropped on his doorstep.
 
His production dropped by half in year one and he was a healthy scratch in the playoffs. Mikkel’s scoring did increase in year two, allowing Wilson to masterfully dump his contract on the Ottawa Senators in the Mike Hoffman fiasco. By year four he was little more than a 5th line player who left to play in Switzerland when his contract expired.
 
 
8. Jonathan Cheechoo
 

Signed By:	Doug Wilson		Position:	F
Date:	2006-02-07		Age July 1st:	25
Term:	5 years		Playoff GP:	31
Total Money:	$15M		Playoff PTS:	16
Cap Hit:	$3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	23.4	272	149	739
Per 82 GP	4.7	82	45	223	15.5

“It’s pretty exciting. When they went out and got Joe Thornton, it shows they want to win. With Doug, we have a good management team and that’s why I agreed to a five-year deal. I just want to play and we have a great young team. They gave me an opportunity and I hope to pay them back.”

– Jonathan Cheechoo

Jonathan Cheechoo’s season goal total was standing at 32 tucks by February 7^th 2006 when he signed this 5-year extension. Cheech would finish the season at 56-goals, and this was an absurdly low price to pay for lighting the lamp that many times. Compared to some of his peers from the same period, this looked like larceny. The winger could have been UFA in 2 years, instead delaying his first crack at the open market until age 30.
 
I’ve got a pretty good idea what Doug Wilson might have said to Jonny to get his autograph on this treaty; “everything you’re doing right now is because of Jumbo. If you get demoted to a lower line before becoming UFA and your goals dry up, you won’t be able to get nearly this much on the open market. This way you have 5 years of security.”
 
Cheechoo never again came close to 56 goals, and saw his goal and shot totals shrink substantially each season. He pumped a respectable 37 tucks in year one, but would eventually be traded to the Ottawa Senators in year three with Milan Michalek and a draft pick for Dany Heatley. He played one season in Ottawa before the Senators bought out the remainder of the contract.
 
 
9. Craig Rivet
 

Signed By:	Doug Wilson		Position:	D
Date:	2007-06-22		Age July 1st:	32
Term:	4 years		Playoff GP:	19
Total Money:	$14M		Playoff PTS:	7
Cap Hit:	$3.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	20.8	253	78	281
Per 82 GP	5.2	82	25	91	19.1

"When we acquire a player, we do a lot of due diligence. We were thinking he would be a stabilizing influence and a veteran player for us for a long time."

– Doug Wilson

Doug Wilson traded the 1^st round draft pick that became Max Pacioretty to Montreal to acquire veteran defenseman Craig Rivet, who was a pending unrestricted at the age of 32. Then 8 days before July 1st, Wilson retained Rivet on a 4-year extension. Craig was actually pretty good in year one, scoring a career high 35 PTS.
 
Doug pulled off a marvelous “sell high” that summer, flipping Rivet to the Buffalo Sabres for a pair of 2nd round draft picks. This took a turn for the worse in Buffalo, as the Sabres bore the brunt of the badness. By year four Rivet’s returns had diminished down to 4 PTS in 37 GP at age 36 before getting claimed on waivers by Columbus. He never signed another NHL contract.
 
 
10. Kevin Labanc
 

Signed By:	Doug Wilson		Position:	F
Date:	2020-10-10		Age July 1st:	24
Term:	4 years		Playoff GP:	0
Total Money:	$18.9M		Playoff PTS:	0
Cap Hit:	$4.7M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	19.0	76	34	165
Per 82 GP	4.8	82	37	178	15.6

"I just gambled on myself"

– Kevin Labanc

Kevin Labanc did a huge favor for Doug Wilson on his previous contract when the Sharks were in a cap crunch (accepting $1M when he should have been worth at least $3M after a 56-point season), so Doug owed him. Sadly for San Jose, Labanc’s production would decline substantially in the next 3 seasons, bottoming out 23 PTS per 82 GP in 2021/22, which was year two of this treaty. He started finding some success on the top line with Couture and Meier in year three, so may rise into his pay grade eventually, but this proved to be just a bad contract on a bad team.
 
 
11. Kyle McLaren
 

Signed By:	Doug Wilson		Position:	D
Date:	2005-08-11		Age July 1st:	29
Term:	3 years		Playoff GP:	16
Total Money:	$7.5M		Playoff PTS:	4
Cap Hit:	$2.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	12.4	128	28	82
Per 82 GP	4.1	82	18	53	20.0

"Kyle is a big, strong, punishing defenseman who is trending up in his career and he will continue to be one of our anchors on the back end."

– Doug Wilson

Doug Wilson wouldn’t have been expecting much of an offensive contribution when he re-signed Kyle McLaren to this 3-year deal, paying instead for the veteran defenseman to throw his body around and punish opposing players. But as Kyle had already played over 600 games (including playoffs), years of gruelling punishment started to take their toll.
 
Kyle was beginning to slow down at a time when the rest of the league was speeding up. By year three McLaren cleared waivers and spent the season in the AHL. That marked the end of his professional hockey career.
 
 
12. Adam Burish
 

Signed By:	Doug Wilson		Position:	F
Date:	2012-07-01		Age July 1st:	29
Term:	4 years		Playoff GP:	6
Total Money:	$7.4M		Playoff PTS:	0
Cap Hit:	$1.9M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	9.1	81	6	70
Per 82 GP	2.3	82	6	71	10.5

“Adam is rugged, aggressive and brings a physical presence night in and night out”

– Doug Wilson

 
“Whether it was injuries or whatever, it just didn’t work”

- Doug Wilson

Adam Burish was never able to attain double digit points as a Chicago Blackhawk, but did have an offensive quasi-renaissance in Dallas, where he set a new career high with 19 PTS before becoming UFA at age 29. Doug Wilson bestowed him a 4-year treaty on July 1st at a salary twice as big as his stat line should have warranted.
 
Obviously Wilson wasn’t bringing him to San Jose to score, as he would be deployed in a more defensive physical role. Unfortunately, not even that part of it worked out. A back injury did cost him most of year two, playing under 10 minutes per game when he was healthy. By year three, he found his scoring touch once again, potting 19 PTS in 54 GP for the San Jose Worcester Sharks, after which the remainder was bought out.
 
 
13. Douglas Murray
 

Signed By:	Doug Wilson		Position:	D
Date:	2008-09-24		Age July 1st:	29
Term:	4 years		Playoff GP:	53
Total Money:	$10M		Playoff PTS:	11
Cap Hit:	$2.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	13.5	255	41	285
Per 82 GP	3.4	82	13	92	19.2

"He brings an ingredient of toughness in addition to the rest of his game. He's shown tremendous growth over the last few years, and we look forward to that continuing."

– Doug Wilson

Douglas Murray never brought offensive upside to the table, earning his money with physicality deployed in a defensive role. He had taken the slow road to the NHL and didn’t have a prohibitive amount of damage on his odometer, but was still a risk.
 
The defenseman would have a decent first season, but began so see his ice time decline after that. By year three the offense had dried up too. Wilson still managed to trade Murray to the Pittsburgh Penguins as a rental for a pair of 2nd round draft picks, a nice haul. Murray signed one more deal in Montreal that turned sour. He played 8 more games in Germany then retired from hockey.
 
 
14. Brenden Dillon
 

Signed By:	Doug Wilson		Position:	D
Date:	2015-06-29		Age July 1st:	24
Term:	5 years		Playoff GP:	65
Total Money:	$16.4M		Playoff PTS:	10
Cap Hit:	$3.3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	17.8	389	79	396
Per 82 GP	3.6	82	17	83	17.5

"Brenden is an important part of this team going forward and we look forward to him playing an integral role on our blue line for years to come"

– Doug Wilson

Doug Wilson traded Jason Demers and a 3rd pick to acquire Brenden Dillon in November 2014 and signed him to a new 5-year extension the following June. The price was nearly double what this level of player should get paid, so Wilson likely believed the youngster would grow into earning his wage. They bought 2 years of unrestricted free agency, which often comes with a wage premium early in the contract.
 
Over the first two seasons he averaged 16.6 minutes of ice per game, which was far too low for his pay grade.  Dillon did show growth in his offensive output, coming close to earning his salary on the back half of the deal. Not a terrible contract, but still an overpayment. Wilson was able to trade him as a rental to the Washington Capitals for 2nd and 3rd round draft picks.
 
 
15. David Schlemko
 

Signed By:	Doug Wilson		Position:	D
Date:	2016-07-01		Age July 1st:	29
Term:	4 years		Playoff GP:	6
Total Money:	$8.4M		Playoff PTS:	3
Cap Hit:	$2.1M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	9.0	117	25	185
Per 82 GP	2.2	82	18	130	17.6

"David is a solid puck-moving defenseman with good speed who can play the game at both ends. He is coming off of a very productive season in New Jersey and we think he will fit well with our group."

– Doug Wilson

David Schlemko came to San Jose as an unrestricted free agent defenseman on July 1st 2016, a day that will go down in infamy for cursed contracts. He had just managed to string together the best season of his career before he scratched this winning ticket.
 
His first season in San Jose was decent, so the Vegas Golden Knights decided to claim him in the expansion draft as they were hoarding more veteran defensemen than they could carry. Vegas then flipped Schlemko to the Montreal Canadiens for a 5th round pick, and that’s where this story hit the skids. He played parts of 2 seasons in Montreal, earning a demotion to the farm. The Habs eventually flipped him to Philly for Dale Weise, in a mutual salary dump. The Flyers sent him to the AHL before eventually buying out the final year