San Jose Sharks 20 Worst Contracts in the Salary Cap Era
Recruiting players to come play in San Jose is a much easier task than the challenge faced by GM 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 was now boxed into a precarious situation.
In the league-wide rankings, San Jose slotted much farther down then some of you might have expected given a few doozies at the top, and how perilous their cap situation looked just within the last 2 years. Brent Burns aged well and earned his contract, Erik Karlsson won the Norris trophy making it easier to ship him out, the Evander Kane deal wasn’t exactly “bad” but was bought out, so you can find it here. Aside from dragging around the lifeless body of Marc-Edouard Vlasic and trading Hertl, there aren’t many serious liabilities left on the books. This list does get thin towards the end, which is why it ranked #28 overall.
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 The book is still available on Amazon, though some of the stats on active contracts are now out of date.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 August 31, 2024: Adjusted for $88M cap, stats for active contracts updated. Tomas Hertl was considered for addition, but ultimately it was decided to let him have at least one full season in Vegas before rendering a verdict.
1. Marc-Edouard Vlasic
Adjusted Cap Hit: $59.3M, $7.4M (avg)
Value Returned: $14.6M, $1.8M (avg)
% Earned: 25%
“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.”
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 deserved 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. Martin Jones
Adjusted Cap Hit: $37.2M, $6.2M (avg)
Value Returned: $11.9M, $2.0M (avg)
% Earned: 32%
"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.”
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.
3. Logan Couture
Adjusted Cap Hit: $66.8M, $8.4M (avg)
Value Returned: $44.6M, $5.6M (avg)
% Earned: 67%
“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 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.
4. Paul Martin
Adjusted Cap Hit: $23.0M, $5.8M (avg)
Value Returned: $8.8M, $2.2M (avg)
% Earned: 38%
“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 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.
5. Mark Bell
Adjusted Cap Hit: $11.4M, $3.8M (avg)
Value Returned: $2.8M, $0.9M (avg)
% Earned: 25%
“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.”
“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.
6. Erik Karlsson
Adjusted Cap Hit: $96.1M, $12.0M (avg)
Value Returned: $64.1M, $8.0M (avg)
% Earned: 67%
"I'm excited to continue the chase for the ultimate prize: the Stanley Cup"
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 was 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, winning the Norris trophy. That hardware forced me to drop him lower down the list, and if he can sustain elite production through to the end, it might be removed entirely.
7. Mikkel Boedker
Adjusted Cap Hit: $18.4M, $4.6M (avg)
Value Returned: $7.1M, $1.8M (avg)
% Earned: 39%
"I understand what he can do. He has some untapped upside that we haven't seen yet"
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
Adjusted Cap Hit: $24.9M, $5.0M (avg)
Value Returned: $16.5M, $3.3M (avg)
% Earned: 66%
“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’s season goal total was standing at 32 tucks by February 7th 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
Adjusted Cap Hit: $22.2M, $5.5M (avg)
Value Returned: $12.1M, $3.0M (avg)
% Earned: 55%
"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 traded the 1st 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
Adjusted Cap Hit: $20.2M, $5.0M (avg)
Value Returned: $8.0M, $2.0M (avg)
% Earned: 40%
"I just gambled on myself"
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, but once the stars were shipped out or injured, Labanc’s production dried up. This may get moved higher in the next update.
11. Kyle McLaren
Adjusted Cap Hit: $13.1M, $4.4M (avg)
Value Returned: $6.5M, $2.2M (avg)
% Earned: 49%
"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 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
Adjusted Cap Hit: $10.0M, $2.5M (avg)
Value Returned: $3.1M, $0.8M (avg)
% Earned: 31%
“Adam is rugged, aggressive and brings a physical presence night in and night out”
“Whether it was injuries or whatever, it just didn’t work”
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. Brenden Dillon
Adjusted Cap Hit: $19.2M, $3.8M (avg)
Value Returned: $9.3M, $1.9M (avg)
% Earned: 48%
"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 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.
14. Douglas Murray
Adjusted Cap Hit: $14.5M, $3.6M (avg)
Value Returned: $8.7M, $2.2M (avg)
% Earned: 60%
"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."
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.
15. Evander Kane
Adjusted Cap Hit: $52.3M, $7.5M (avg)
Value Returned: $23.4M, $3.4M (avg)
% Earned: 45%
The San Jose Sharks acquired Evander Kane from the Buffalo Sabres before he was set to become an unrestricted free agent, and Wilson signed him to a 7-year contract that initially started off productive. This was only added to the list in 2023 because he mostly earned his money until it was terminated for violating AHL Covid protocol. He filed a grievance that the team had insufficient grounds to terminate his contract and withhold the rest of his money, which he won. Because he had already signed a new contract with Edmonton for a similar amount of money, they agreed to just make him whole and end the relationship. I personally feel like this should have been treated like a buyout and Evander should have been entitled to the money from both teams. There must have been legal reasons why that would have been prohibitive. Technically the Sharks financial liability here was reasonably small, but it still makes the list as an embarrassing episode for both sides.
16. David Schlemko
Adjusted Cap Hit: $9.7M, $2.4M (avg)
Value Returned: $4.7M, $1.2M (avg)
% Earned: 48%
"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."
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.
17. Brad Stuart
Adjusted Cap Hit: $14.6M, $4.9M (avg)
Value Returned: $8.0M, $2.7M (avg)
% Earned: 55%
“I can be a guy that can play in the top four and just be steady, physical, and play some hard minutes, penalty kill”
Brad Stuart had been an effective defenseman with the Detroit Red Wings for 4 years, playing an important role in their 2008 Stanley Cup victory. Stuart had played his first 7 seasons in San Jose before getting traded to Boston in the Joe Thornton trade, and his heart yearned for a return to California.
Brad signed this 3-year contract at age 32 and saw an immediate decline in his PTS production, going from 21 PTS in 81 GP down to 6 PTS in 48 GP in year one. After 2 years, Wilson traded him to Colorado for 2nd and 6th round draft picks. Not a bad haul for a 34-year-old declining defenseman.
18. Radim Simek
Adjusted Cap Hit: $9.6M, $2.4M (avg)
Value Returned: $3.1M, $0.8M (avg)
% Earned: 33%
Radim Simek received an expensive extension from Doug Wilson shortly before Covid shut-down the rest of the NHL season, having never played a full campaign in the NHL. The extension, despite early promise, carried risk due to his injury history. His susceptibility to injuries made his long-term deal concerning. The investment risked tying up cap space in a player whose availability and performance were uncertain. His usage declined for the first two years, even as the Sharks traded away their blueline depth and desperately needed anyone to fill their minutes, he became a healthy scratch. That’s too much money to watch from the press box. He was demoted to the AHL, and this might get moved higher in the next update.
19. Raffi Torres
Adjusted Cap Hit: $8.0M, $2.7M (avg)
Value Returned: $2.3M, $0.8M (avg)
% Earned: 29%
“Every player comes with some level of risk and obviously we’re very comfortable with this. He’s really transformed and evolved his game. He’s a very effective player. I won’t comment and can’t comment on the suspension in the playoffs. We think he brings all the skill sets we’re looking for: speed, strength, he can shoot and he has a high skill level to play with high-end players.”
“He’s not playing, he’s suspended”
- Slapshot
Doug Wilson traded a 3rd round pick to rent Raffi Torres from the Phoenix Coyotes, signing the controversial banger to a 3-year deal. It was nearly identical to what Jordin Tootoo signed with the Red Wings one year earlier (which you can read about on the Wings worst contracts list).
Torres would miss most of the first 2 seasons with an injury, then came year three. Raffi delivered a dirty hit in preseason and received a 41-game suspension as a repeat offender. When he returned, San Jose dumped the rest of this contract on the Maple Leafs with a pair of 2nd round picks to add Nick Spaling and Roman Polak, but Raffi never played in Toronto. This contract marked the end of Torres NHL career.
20. Tyler Kennedy
Adjusted Cap Hit: $6.4M, $3.2M (avg)
Value Returned: $1.8M, $0.9M (avg)
% Earned: 28%
The San Jose Sharks sent a second round pick to the Pittsburgh Penguins for Tyler Kennedy one year before he was set to become an unrestricted free agent, locking him into a 2-year deal a few days later. This was a pay raise on his previous contract, yet Tyler’s last season in Pittsburgh saw a substantial drop in scoring rate from 45 down to 20. This regression did not deter Wilson from raising the stakes, as he had to believe the winger would return to form in a new environment. The answer proved to be no. He was never that good again. In the last year they dumped him on the Islanders for a 7th round pick. Kennedy was out of the league a year later.