Sunday, February 26, 2023

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 The book is still available on Amazon, though some of the stats on active contracts are now out of date.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

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The Winnipeg Jets have spent the last decade under the astute management of Kevin Cheveldayoff, who has made relatively few egregious errors at the negotiating table, at least compared to some of his peers who have governed that long. The franchise struggled mightily over the first 10 years of the salary cap era, struggling to overcome their calamitous start as an expansion team in 1998.

It was Don Waddell who managed the Thrashers Jets for the first 12 years of their existence, resulting in one playoff appearance. While he might be celebrated for the job he’s done in Carolina, he laid a poor foundation in Atlanta Winnipeg that took Chevy years to tear down and rebuild. During the 2020 Covid Cup, I was concerned that I would lose Zach Bogosian from this list, then remembered that Buffalo terminated his contract, with Zach signing a new one in Tampa before winning a championship.
 
The Jets had to rebuild on the fly in 2019/20 after a disastrous exodus of defensemen led them to fall short of a playoff spot, but fortunately their roster is not currently saddled with any overly onerous contracts. Bryan Little was going to be high on the ranks, but received an injury exemption after booking an all-inclusive vacation to Robidas Island.
 
 
1. Zach Bogosian
 

Signed By:

Kevin Cheveldayoff

Position:

D

Date:

2013-07-29

Age July 1st:

22

Term:

7 years

 

Playoff GP:

18

Total Money:

$36M

 

Playoff PTS:

4

Cap Hit:       

$5.1M

 

Stanley Cups:

1

 

 

Adj Cap Hit

GP

PTS

SOG

ATOI

Total

40.7

347

93

604

 

Per 82 GP

5.8

82

22

143

21.6

“I made it clear since obviously my first time being in Winnipeg it was obviously a place that I wanted to be for a long time”
Zach Bogosian was the third overall draft pick in 2008 and was immediately rushed to the NHL by Thrashers Jets management. It might have been better for his development to take the longer path to the big stage, as young defensemen tend to take longer to acclimate to pro hockey. Zach hasn’t had a fully healthy season since age 19, as injuries did contribute to the negativity of this treaty. They paid him like a 40-point top pairing defenseman, and the results were nowhere near that sum.
 
For the Jets part, it was not bad at all. Cheveldayoff was able to flip Bogosian to the Buffalo Sabres with Evander Kane to get Tyler Myers among other quality assets. It was the Sabres who bore the brunt of Zach’s demise. Chevy cashed out at the right time. This contract might have been eligible for injury exemption, however Bogo had injury issues prior to this deal, and was still $2M overpaid on a per 82 GP basis.
 
 
2. Bobby Holik
 

Signed By:

Don Waddell

Position:

F

Date:

2005-08-02

Age July 1st:

34

Term:

3 years

 

Playoff GP:

4

Total Money:

$12.75M

 

Playoff PTS:

1

Cap Hit:       

$4.25M

 

Stanley Cups:

0

 

 

Adj Cap Hit

GP

PTS

SOG

ATOI

Total

23.9

228

96

481

 

Per 82 GP

8.0

82

35

173

16.4

"I didn't expect to be in this situation. Things didn't work out. That's O.K. You move on."
Bobby Holik was an expensive mistake for the New York Rangers prior to the 2004/05 lockout, when they overpaid for a defensive center who had won 2 Stanley Cups in New Jersey. Bobby only managed to play 2 seasons in the Big Apple (scoring 54 PTS in 2004) before becoming a compliance buyout for the Rangers after the salary cap was introduced. Thrashers Jets GM Don Waddell made the same mistake, albeit for less term.
 
Holik would go on to average 35 PTS per 82 GP in Atlanta Winnipeg, the type of production you might expect from a $3.5M center. Unfortunately, Bobby was locked in at an $8M pay grade (adjusted for cap inflation). That’s awful. Perhaps I’m not appropriately valuing his defensive contribution, but it couldn’t have been that good given Atlanta Winnipeg was among the league’s worst defensive teams, finishing dead last in goals against in year three.
 
 
3. Ondrej Pavelec
 

Signed By:

Kevin Cheveldayoff

Position:

G

Date:

2012-06-25

Age July 1st:

24

Term:

5 years

 

Playoff Wins:

0

Total Money:

$19.5M

 

Playoff SV%:

0.891

Cap Hit:       

$3.9M

 

Stanley Cups:

0

 

 

Avg Adj Cap Hit

GP

W

GAA

SV%

Total

4.7

192

82

2.75

0.907

"I'm really happy that I have the chance to stay here in Winnipeg and stay for five years. That's all you're looking for, to stay in the city you like with the great fans there.”
Ondrej Pavelec had spent most of his career as a below average goaltender at the time this deal was signed, and he continued that legacy on this long-term pact. Many people thought Pavelec was a future star based on stretches of outstanding play, but consistency was his biggest problem. Anyone who played fantasy hockey over these years knew Pav as one of the prototypical hot and cold goaltenders that was great at times, but the risk of a blow out any given night was especially high.
 
Pavelec had one good season under this contract with 50 GP and 2.28 GAA, .920 SV% in year three. During the lockout shortened 2013 season, Ondrej played in 44 of the team’s 48 GP, and that heavy usage gave him a high expected free agent value despite -9 goals saved above average. Pavelec was simply not good enough to carry a team as a starting goalie and made too much money at the position for the team to bring in a legit veteran starter. Eventually he was supplanted by Connor Hellebuyck, and the Jets became contenders.
 
 
4. Toby Enstrom
 

Signed By:

Kevin Cheveldayoff

Position:

D

Date:

2012-07-27

Age July 1st:

28

Term:

5 years

 

Playoff GP:

15

Total Money:

$28.8M

 

Playoff PTS:

1

Cap Hit:       

$5.8M

 

Stanley Cups:

0

 

 

Adj Cap Hit

GP

PTS

SOG

ATOI

Total

33.7

317

89

291

 

Per 82 GP

6.7

82

23

75

21.8

“The move to Winnipeg was fun and it feels like we have a good thing going on. I really like playing in front of all the fans in that city and it made me want to stay. I’m really happy I came to agreement with the Winnipeg Jets.”
Toby Enstrom posted back to back 50-point seasons in 2010 and 2011, then signed an early extension in 2012 after scoring 33 PTS in 62 GP (44-point pace), missing 20 games with an injured collar bone. Toby then re-injured that collarbone in the lockout shortened 2013 season with the contract already signed, and never came close to a 50-point pace again. He played a full 82 games in year one, scoring 30 PTS, averaging almost 24 minutes per night. Then the tailspin began as the positive contributions faded.
 
Over these 5 seasons his point totals were (30, 23, 16, 14, and 6). Injuries did contribute to his decline. Kevin Cheveldayoff skillfully convinced Toby to waive his no movement clause so he could be left unprotected in the expansion draft, but then traded a pair of draft picks so the Knights wouldn’t take Toby. The Jets traded down in the entry draft to select Kristian Vesalainen while Vegas took Nick Suzuki with their 13th pick, which is not aging well for Winnipeg.
 
By the end, Enstrom couldn't even get on the ice when healthy. He never played in the NHL again.
 
 
5. Steve Mason
 

Signed By:

Kevin Cheveldayoff

Position:

G

Date:

2017-07-01

Age July 1st:

29

Term:

2 years

 

Playoff Wins:

0

Total Money:

$8.2M

 

Playoff SV%:

1.000

Cap Hit:       

$4.1M

 

Stanley Cups:

0

 

 

Avg Adj Cap Hit

GP

W

GAA

SV%

Total

4.4

13

5

3.24

0.906

“Our goal is going to be able to provide the Jets with some real consistent, strong goaltending night in and night out, regardless of who is in the net. I definitely look at the Winnipeg situation as a spot where I can come in and help a team succeed, have a chance to play some hockey games and meaningful hockey games down the stretch and hopefully into the playoffs.”
Steve Mason had spent the preceding 4 seasons as the majority starter in Philadelphia, peaking at a .928 SV% in 51 GP in 2015. That save percentage dropped 10% each of the next two seasons before Mason made his first trip to the UFA market. There may not have been any long-term suitors, but he solicited a decent salary from the Jets on a short-term treaty. At this price they had to see him as more than just a mentor, that’s 1B starter money.
 
Mason’s first year in Winnipeg was a 100% bust with a 3.24 GAA and .906 SV% and was bought out before year two. This might have been okay if they brought him in as a back-up and paid him second string money, unfortunately they paid him like a goalie you’d want to play 30-50 games. The best thing about Mason’s tenure was that it brought out the very best in Hellebuyck, who played at a Vezina caliber level. Perhaps you could argue that bringing in Mason was worthwhile because it helped elevate their goalie of the future into the stratosphere. Hellebuyck’s play did decline the season after Mason left, so maybe…
 
 
6. Mark Stuart
 

Signed By:

Kevin Cheveldayoff

Position:

D

Date:

2014-03-05

Age July 1st:

30

Term:

4 years

 

Playoff GP:

4

Total Money:

$10.5M

 

Playoff PTS:

2

Cap Hit:       

$2.6M

 

Stanley Cups:

0

 

 

Adj Cap Hit

GP

PTS

SOG

ATOI

Total

12.0

176

21

114

 

Per 82 GP

3.0

82

10

53

16.6

“There was some interest. We could have gone into a selling mode very, very easily. When you really want to get into that mode, you have to be extremely aggressive with it. When the calls did come with respect to some of our UFAs … you have to set your own thoughts on what you would like in return, or if you want to go into that mode.”
Mark Stuart was scheduled to become an unrestricted free agent at age 30, and had the potential to be sold as a rental in a season where the Jets were not in contention. Chevy opted instead to give Stuart a 4-year extension. The red flag here was 30-years-old and 1000 career hits. That’s a high-risk category for a long-term commitment. Stuart was never an offensive contributor, deployed more for his physicality.
 
Stuart came close to earning his salary in year one of the contract, but it was a steady downward slide after that, leading to the Jets buying out the final year. Despite being a “heart and soul” player, he quickly fell below the threshold of play needed to sustain NHL employment. Mark was unable to secure another NHL job after this buyout, and went to play a season in Germany before retiring. They used some of these cap savings to go out and sign Dmitri Kulikov.
 
 
7. Dmitry Kulikov
 

Signed By:

Kevin Cheveldayoff

Position:

D

Date:

2017-07-01

Age July 1st:

26

Term:

3 years

 

Playoff GP:

7

Total Money:

$13M

 

Playoff PTS:

0

Cap Hit:       

$4.3M

 

Stanley Cups:

0

 

 

Adj Cap Hit

GP

PTS

SOG

ATOI

Total

13.7

170

27

142

 

Per 82 GP

4.6

82

13

68

17.5

"I had some options. When I was making the decision, I was looking at the rosters of the teams that are more closer to contending for the Cup than anything else, and the Winnipeg Jets, I made a decision to join the team because I feel like it's the team that has all the pieces and they're moving in the right direction”
Dmitry Kulikov had options when he reached the UFA market at age 26, but perhaps none as generous as this, considering he had just completed a season with 5 PTS in 47 GP for the Sabres (missing half the season with a back injury). The Russian defenseman had flashed more offensive upside in his younger years, but that output had been trending downwards prior to the Jets signing him to this 3-year deal.
 
They may have been buying damaged goods, as Kulikov required back surgery in year one with the Jets, costing him several weeks. He was reduced to a bottom pairing role in year two, and often found himself as a healthy scratch. The usage did pick up in the final year after the abrupt departure of Myers, Trouba, and Byfuglien, but he still wasn’t worth the price that was paid. His next contract would be with New Jersey for ¼ of the cost.
 
 
8. Ron Hainsey
 

Signed By:

Don Waddell

Position:

D

Date:

2008-07-02

Age July 1st:

27

Term:

5 years

 

Playoff GP:

0

Total Money:

$22.5M

 

Playoff PTS:

0

Cap Hit:       

$4.5M

 

Stanley Cups:

0

 

 

Adj Cap Hit

GP

PTS

SOG

ATOI

Total

30.9

346

107

461

 

Per 82 GP

6.2

82

25

109

21.2

"He moves the puck well, has good offensive capabilities and is a solid all-around defenceman who has taken significant strides with his game over the last few seasons."
Ron Hainsey was not a bad acquisition by Atlanta Winnipeg, he was simply paid too much for his services. Don Waddell cited “offensive capabilities” on the menu when he made this long-term commitment to the 27-year-old on July 2nd, 2008 and paid Hainsey like an offensive producer.
 
Year one actually produced good results, the best season of Hainsey’s career with 39 PTS (thanks to 3.7 minutes per game of power play time). As the power play deployment began to decline, so did Hainsey’s point production, as he started growing into more of a defensive role. The lowest point was year four when he produced just 10 PTS in 56 GP. If you need more evidence that this was a failure, the team played zero playoff games during this tenure.
 
 
9. Mathieu Perreault
 

Signed By:

Kevin Cheveldayoff

Position:

F

Date:

2016-07-07

Age July 1st:

29

Term:

4 years

 

Playoff GP:

22

Total Money:

$16.5M

 

Playoff PTS:

5

Cap Hit:       

$4.1M

 

Stanley Cups:

0

 

 

Adj Cap Hit

GP

PTS

SOG

ATOI

Total

17.2

257

104

362

 

Per 82 GP

4.3

82

33

116

12.9

"His game, it's an infectious game. He's a guy that likes the puck on his stick and can make plays. Good on the power plays, can play center, can play wing. Shown his versatility in a lot of different areas.”
Mathieu Perreault had posted back-to-back-to-back 40+ point seasons (averaging over 16 minutes per game) and was scheduled to become an unrestricted free agent at age 29 when the Jets locked him into this 4-year extension. He was an effective top six forward, praised for his versatility up and down the line-up.
 
The usage and scoring output both dropped in year one, but was still at a respectable level. Then he celebrated his 30th birthday, and took an even steeper dive by year two into the bottom six group, with 31 PTS and 12.2 minutes per game. He scored 14 PTS in 49 GP as the Jets missed the playoffs (sort of) in year three.
 
 
10. Jim Slater
 

Signed By:

Kevin Cheveldayoff

Position:

F

Date:

2012-06-13

Age July 1st:

29

Term:

3 years

 

Playoff GP:

4

Total Money:

$4.8M

 

Playoff PTS:

0

Cap Hit:       

$1.6M

 

Stanley Cups:

0

 

 

Adj Cap Hit

GP

PTS

SOG

ATOI

Total

6.0

135

17

97

 

Per 82 GP

2.0

82

10

59

9.7

“I told my agent right from the beginning that Winnipeg was definitely tops of my list and if everything seemed to work out then that’s the place I wanted to be”
Jim Slater spent his entire NHL career with the Jets after getting drafted by Atlanta Winnipeg in 2002, and set a career high in goals and PTS when he signed this 3-year deal before the 2012/13 lockout. Slater expressed a strong desire to stay in the only NHL city he’d ever known.
 
When the league returned from the work stoppage, Slater played 26 games, scoring 2 PTS, averaging 10.5 minutes per game. Over these 3 seasons, he scored 17 PTS in 135 GP, averaging under 10 minutes per game. They signed him as a mildly productive 3rd line player, and what they got was a replacement level center who should have been paid under $1M. Slater did suffer multiple injuries over the first 2 years, and might have been eligible for an injury exemption if he wasn’t also significantly overpaid on a “per 82 GP” basis.
 
 
11. Shawn Matthias
 

Signed By:

Kevin Cheveldayoff

Position:

F

Date:

2016-07-01

Age July 1st:

28

Term:

2 years

 

Playoff GP:

0

Total Money:

$4.3M

 

Playoff PTS:

0

Cap Hit:       

$2.1M

 

Stanley Cups:

0

 

 

Adj Cap Hit

GP

PTS

SOG

ATOI

Total

4.7

72

15

77

 

Per 82 GP

2.4

82

17

88

12.7

"We were looking to add someone that could give us another option for Paul to use on the PK. He can play centre, he has played centre, but I wouldn't say that's where he's penciled in yet.” 
                                                                                                Kevin Cheveldayoff
Shawn Matthias scored 28 PTS in 71 GP before hitting unrestricted free agency at age 28, earning himself a nice pay day for a bottom 6 winger. This was similar to the deal Michael Raffl had inked a few months earlier, but slightly less money and term.
 
Shawn’s time in Winnipeg was doomed from the start, suffering multiple injuries over the course of his first season, limiting him to 12 PTS in 45 GP. Matthias spent most of the second season either injured or watching from the press box as a healthy scratch, collecting just 3 PTS in 27 GP. Shawn retired from hockey when this contract was over.
 
 
12. Olli Jokinen
 

Signed By:

Kevin Cheveldayoff

Position:

F

Date:

2012-07-02

Age July 1st:

33

Term:

2 years

 

Playoff GP:

0

Total Money:

$9M

 

Playoff PTS:

0

Cap Hit:       

$4.5M

 

Stanley Cups:

0

 

 

Adj Cap Hit

GP

PTS

SOG

ATOI

Total

11.5

127

57

256

 

Per 82 GP

5.8

82

37

165

17.1

“He has the size, he’s got a tremendous amount of experience, he’s had great consistency over the years”
Olli Jokinen came to Winnipeg in July 2012 at age 33 after scoring 61 PTS for the Calgary Flames. The veteran of over 1000 NHL games was handling the aging process very well for a big man, and had productive seasons past his 30th birthday. That was until this contract was signed, because year one was his worst in a decade, potting just 14 PTS in 45 GP (26-point pace) during the lockout shortened 2013 season.
 
Olli did bounce back in year two, but the damage was done. They paid him close to $6M in average adjusted cap hit over 2 seasons and received 57 PTS in 127 GP (37-point pace).
 
 
13. Drew Stafford
 

Signed By:

Kevin Cheveldayoff

Position:

F

Date:

2015-06-30

Age July 1st:

29

Term:

2 years

 

Playoff GP:

6

Total Money:

$8.7M

 

Playoff PTS:

2

Cap Hit:       

$4.3M

 

Stanley Cups:

0

 

 

Adj Cap Hit

GP

PTS

SOG

ATOI

Total

9.9

136

59

296

 

Per 82 GP

5.0

82

36

178

16.0

"I think the term works good for both sides. I'm all for the challenge of raising my game."
Drew Stafford came to Winnipeg as part of the Tyler Myers trade and signed a 2-year deal with the Jets instead of testing unrestricted free agency at age 29. The salary was high, but fortunately the term was reasonable.
 
The winger did manage to score 21 goals in year one, but dropped down to 8 Goals in 58 GP in year two after a significant reduction in ice time. Management was able to sell him off as a rental to the Bruins for a 5th round draft pick to salvage some value. Stafford’s next contract was for close to the league minimum, as his career was near the end of the road.
 
 
14. Garnet Exelby
 

Signed By:

Don Waddell

Position:

D

Date:

2007-07-17

Age July 1st:

25

Term:

3 years

 

Playoff GP:

0

Total Money:

$4.2M

 

Playoff PTS:

0

Cap Hit:       

$1.4M

 

Stanley Cups:

0

 

 

Adj Cap Hit

GP

PTS

SOG

ATOI

Total

6.3

189

18

93

 

Per 82 GP

2.1

82

8

40

15.8

"He's made himself into a very dependable player. He's an every-nighter who plays hard against any player who's on the ice."
Garnet Exelby never had much offensive upside, even at the minor league level. He earned a job in the NHL by being a hard-nosed defensive defenseman, pilling up 257 penalty minutes in the AHL as a rookie pro. Don Waddell inked him to a reasonable 3-year deal at age 25.
 
Year one very nearly received a passing grade as Exelby reached a career high in average ice time, but his deployment would sink in the seasons that followed. After year two, he was traded to the Maple Leafs with Colin Stuart for Pavel Kubina and Tim Stapleton. Garnett hit a new low, scoring 4 PTS and averaging 10 minutes per game of ice time. He never played in the NHL again.
 
 
15. Chris Mason
 

Signed By:

Rick Dudley

Position:

G

Date:

2010-07-01

Age July 1st:

34

Term:

2 years

 

Playoff Wins:

0

Total Money:

$3.7M

 

Playoff SV%:

0.000

Cap Hit:       

$1.85M

 

Stanley Cups:

0

 

 

Avg Adj Cap Hit

GP

W

GAA

SV%

Total

2.5

53

21

3.09

0.894

"Chris has proven himself as an elite-level goaltender and we have the utmost confidence in his capabilities. We are pleased to add him to our organization are excited to follow his lead into the playoffs."
Chris Mason was a slightly above average starting goaltender before signing this contract at age 34 at half the price you’d normally pay for a 60-start goaltender. The Jets had used the 1A/1B tandem of Johan Hedberg and Ondrej Pavelec the year before and brought Mason in to challenge Pavelec as a primary starter.
 
This experiment was a failure. In 53 GP he posted an .894 SV% and 3.09 GAA. That’s bad, even for a back-up. After this contract, Mason would go on to play 11 more games in the NHL before leaving North America to try his luck in the Italian league.
 

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