New York Islanders 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 The book is still available on Amazon, though some of the stats on active contracts are now out of date.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 New York Islanders had some rough years during the reign of Garth Snow, missing the playoffs more often than not, and signing some really bad contracts. Their number one biggest blunder was Rick DiPietro, which played a role in innovating a new type of contract designed for salary cap circumvention.
 
Garth Snow was the man in charge for over a decade, which is why his name dominates this list, as the architect of many fantastical follies. It was a mystery how he was able to maintain this employment for as long as he did, given the lack of success on the ice and some of the blunders he made off the ice. It’s entirely plausible that no General Manager has ever kept their job that long with fewer playoff wins, but I’ll leave that for someone else to confirm.
 
Eventually Lou Lamoriello would replace the Snowman, and he was awarded Executive of the year in 2020 after the team advanced to the Conference final, their most successful campaign in the entire salary cap era. Lou’s reign hasn’t been perfect, and he may yet have to pay the piper for over-paying his 4th line, like losing Devon Toews. Hard to say if the team is on its way up or on its way down.
 
 
1. Rick DiPietro
 

Signed By:	Garth Snow		Position:	G
Date:	2006-09-12		Age July 1st:	24
Term:	15 years		Playoff Wins:	1
Total Money:	$67.5M		Playoff SV%:	0.898
Cap Hit:	$4.5M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	5.8	175	72	2.89	0.904

"In all of our discussions with Rick, he made it clear that he wanted to be an Islander for the rest of his career, but it was of equal importance to Rick that we work out a deal that would allow us to continue to build a Stanley Cup contender for years to come. This deal is great news for our franchise and our fans."

– Garth Snow

When Garth Snow signed Rick DiPietro to this 15-year contract in 2006, it sent shockwaves through the hockey world. Regardless of how it would eventually play out, credit Garth for his creativity. This was a minor coup in salary cap circumvention, as nobody had yet conceived the notion of signing free agents to a ridiculously long term in order to get the cap hit down. Unlike the “back-diving” revolution this inspired, DiPietro did not get his agreement front loaded (Mike Richards got a slight back-dive in 2007, then Lecavalier got a full back-dive in 2008).
 
It could be argued that this contract was only bad because DiPietro couldn’t stay healthy. The success of this investment would have been different had DiPietro been able to sustain a high level of goaltending. The former 1st overall draft pick was mostly a league average goaltender for 63 GP the season prior, posting a 3.02 GAA and .900 SV%. He was eventually bought out, but don’t feel bad for Ricky…he’ll be getting $1.5M per year from the Islanders until 2029. Humans will be flying around in starships, he’ll still be cashing Islanders pay cheques.

2. Andrew Ladd
 

Signed By:	Garth Snow		Position:	F
Date:	2016-07-01		Age July 1st:	30
Term:	7 years		Playoff GP:	1
Total Money:	$38.5M		Playoff PTS:	0
Cap Hit:	$5.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	40.2	232	84	350
Per 82 GP	5.7	82	30	124	15.3

“At the end of the day it's not all about money for me. It's about being in a good place for my family and being on a team that's going to contend every year. You'd be crazy not to want to be a part of this group and this organization. We'll see what happens.”

– Andrew Ladd

Garth Snow gave a 7-year contract to a 30-year-old player coming off a 46-point season. This turned sour right out of the gate, with Andrew Ladd dropping down to 31 PTS in 78 GP in year one. He’s a good character guy, but it’s never good to see that large of a point decline happen right away, especially at that age when an athlete is less likely to bounce back.
 
Andrew scored 29 PTS in year two and was in the AHL by year three. This is the greatest contract Kevin Cheveldayoff never signed. Ladd was part of the infamous UFA class of 2016, one of the most astounding collection of calamities in the last 15 years.
 
 
3. Johnny Boychuk
 

Signed By:	Garth Snow		Position:	D
Date:	2015-03-12		Age July 1st:	31
Term:	7 years		Playoff GP:	17
Total Money:	$42M		Playoff PTS:	1
Cap Hit:	$6M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	44.8	332	96	714
Per 82 GP	6.4	82	24	176	19.7

“The organization has been incredible to both myself and my family. I am proud to be an Islander and look forward to competing every night in front of such a passionate fan base for many years to come.”

– Johnny Boychuck

The Islanders traded a pile of picks to get Johnny Boychuck from the Bruins with a year remaining on his previous deal. Johnny reached his personal scoring apex immediately after arriving on Long Island, popping 35 PTS at age 30. He didn’t sign immediately upon arrival, as this dragged out for a few months first. The pressure on Garth Snow to retain his acquisition beyond a single season rental had to be mounting, prompting this 7-year extension to an over-30 player.
 
That’s a recipe for disaster, which is exactly what happened here. Boychuck immediately declined down to 25 PTS in year one and only got worse from there, plummeting to 11 PTS in 64 GP in year five. His average time on ice shrank each season. Had this deal instead been 4 years at $3.5M AAV, it would have been acceptable. To make matters worse, Snow handcuffed management by giving the veteran a full no-movement clause for the first 4 years, and a modified no-trade clause for the last 3, hindering any possible salary dump.
 
 
4. Nikolay Kulemin
 

Signed By:	Garth Snow		Position:	F
Date:	2014-07-02		Age July 1st:	27
Term:	4 years		Playoff GP:	18
Total Money:	$16.8M		Playoff PTS:	6
Cap Hit:	$4.2M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	19.2	248	79	288
Per 82 GP	4.8	82	26	95	14.1

"To me, free agency is like fishing. You put your line in the water and you hope you get some nibbles. We got two big bites today."

– Garth Snow

Nikolay Kulemin’s career trajectory had been trending south for his last 3 years in Toronto after a career peak 57 PTS in 2011. He scored a paltry 20 PTS in 70 GP before hitting the UFA market at age 28. The decline had already been on display for years, and his stat line shouldn’t have been worth anything over $2M. Yet the Russian got more than twice that amount from the Islanders, who never received anything close to what they paid for.
 
Nikolay arrived in New York with Mikhail Grabovski, as the two had been seeking to sign on the same team (you can read more about Grabovski further down this list). Kulemin scored 31 PTS in 82 GP in year one and that’s as good as it got. Upper body surgery did cut his final season short before returning to Russia.
 
 
5. Mikhail Grabovski
 

Signed By:	Garth Snow		Position:	F
Date:	2014-07-02		Age July 1st:	30
Term:	4 years		Playoff GP:	3
Total Money:	$20M		Playoff PTS:	0
Cap Hit:	$5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	22.9	109	44	164
Per 82 GP	5.7	82	33	123	14.2

“Those who cannot remember the past are condemned to repeat it.”

- George Santayana

The Toronto Maple Leafs once gave Mikhail Grabovski a 5-year, $27.4M contract that was quickly bought out after one season. After his unceremonious departure from the center of the hockey universe, Grabo found himself in Washington, where he posted a pedestrian 35 PTS in 58 GP. Garth failed to learn the lesson that Brian Burke Dave Nonis painfully discovered, and signed the center to a similar type of deal.
 
This turned nasty from day one, generating just 19 PTS in 51 GP in the first season. Year two wasn’t much better, before a concussion ended Grabovski’s career. The Islanders would eventually trade him with a 1st round pick to Vegas before the expansion draft.
 
 
6. Anders Lee
 

Signed By:	Lou Lamoriello		Position:	F
Date:	2019-07-01		Age July 1st:	28
Term:	7 years		Playoff GP:	18
Total Money:	$49M		Playoff PTS:	11
Cap Hit:	$7M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	49.3	171	108	434
Per 82 GP	7.0	82	52	208	17.4

"He was our captain and still is our captain. We didn't bring him back. He never left."

– Lou Lamoriello

After losing their previous captain to the New York Islanders, Lou didn’t want history to repeat itself 1 year later, signing Anders Lee to a long-term extension. The UFA winger had made it all the way to July 1st before autographing the ticket, as it was widely speculated that Lou had been pursuing Panarin and Bobrovsky, only deciding to retain Lee once it became clear that the Russians were heading elsewhere.
 
For the first three seasons, he produced at roughly the level of a $5M player who was $2M overpaid. The gap between what he’s worth and what he’s being paid should only increase with age. That’s why he finds himself on this list despite a reasonably successful 2020 playoffs. He could find himself higher up the list in future iterations (or lower if he ages well).
 
 
7. Alexei Zhitnik
 

Signed By:	Mike Milbury		Position:	D
Date:	2005-08-02		Age July 1st:	32
Term:	4 years		Playoff GP:	4
Total Money:	$14M		Playoff PTS:	0
Cap Hit:	$3.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	24.8	203	75	310
Per 82 GP	6.2	82	30	125	22.6

"He's one of the best two-way defensemen in the game and he's a highly-respected player. He's going to play big minutes for us in all situations."

– Mike Milbury

Mike Milbury needed a defenseman to replace Adrian Aucoin after the lockout and the solution was 32-year-old Alexei Zhitnik, who had been in decline prior to the work stoppage. This came at a cheaper price than Aucoin, and was nearly identical to deals signed by Derian Hatcher and Mike Rathje in Philly that same day.
 
There was a resurrection in Zhitnik’s offensive production for the first two years, when he was playing over 24 minutes per game and scoring and a 40-point rate. That allowed the Isles to ship him out of town to the Flyers for Freddy Meyer and a 3rd round draft pick. Where this experiment really hit the skids was year three after he had been traded to Atlanta Winnipeg. The Thrashers Jets would buy out the last year of the contract.
 
 
8. Thomas Hickey
 

Signed By:	Lou Lamoriello		Position:	D
Date:	2018-07-01		Age July 1st:	29
Term:	4 years		Playoff GP:	4
Total Money:	$10M		Playoff PTS:	0
Cap Hit:	$2.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	10.2	47	6	49
Per 82 GP	2.5	82	10	85	18.3

“Am I angry to be here? The answer is no. I’m disappointed things didn’t work out with the Islanders to this point, but I’m a professional hockey player and get to do my job. You make 20-some-odd good new friends. I’m excited to get going with the Tigers.”

– Thomas Hickey

Thomas Hickey was a veteran minor leaguer and former draft bust when the Islanders claimed him off waivers and gave him a shot at a career in the NHL. The defenseman had 4 consecutive seasons close to 20 PTS, then delivered a career high 25 before reaching UFA status at age 29. He went all the way to July 1st, then decided to return to New York.
 
Hickey’s offensive contribution disappeared in year one before suffering a concussion in December that cost him 10 weeks. By year two, he could not crack the Islanders roster and was sent to the AHL. Would this contract have been okay had the concussion never happened? I guess we’ll never know, but he was healthy in year two when he was demoted to the minors.
 
 
9. Cal Clutterbuck
 

Signed By:	Garth Snow		Position:	F
Date:	2016-12-09		Age July 1st:	29
Term:	5 years		Playoff GP:	43
Total Money:	$17.5M		Playoff PTS:	11
Cap Hit:	$3.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	18.1	295	74	355
Per 82 GP	3.6	82	21	99	13.5

“It doesn’t matter if you play against Martin or Shuttlebuck, or whatever it is, I hate that guy”

– Robert Hagg

There is nothing wrong with having some bangers on your 3rd and 4th lines to help wear down the opposition, especially over the course of a 7-game playoff series. The problem with this particular contract is that Cal Clutterbuck is being compensated at triple the rate that a one-dimensional banger should be worth. Historically this type of player tends to be widely available and cost under $2M AAV. You can always find a Pat Maroon in the bargain bin.
 
Another issue with this particular treaty, Cal turned 30-years-old early in the first season on a 5-year term. Players who accumulate substantial hit numbers over an extended period of time are more likely to wear down quickly as they age. He may have helped the Islanders advance to the 2020 Conference final, but his salary was among the reasons that Devon Toews needed to be shipped out. There is an opportunity cost to overpaying your 4th line.
 
 
10. Leo Komarov
 

Signed By:	Lou Lamoriello		Position:	F
Date:	2018-07-01		Age July 1st:	31
Term:	4 years		Playoff GP:	43
Total Money:	$12M		Playoff PTS:	7
Cap Hit:	$3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	12.2	164	48	151
Per 82 GP	3.1	82	24	76	13.3

"Individual players win games, but teams win championships"

– Lou Lamoriello

Leo Komarov hit his peak scoring 19 goals and 36 PTS in 67 GP at age 28 in 2016 for the Toronto Maple Leafs. Over his final 2 seasons in Toronto, Leo’s scoring rate per 82 GP dropped more than 10 PTS each year before reaching the UFA market at age 31. Lou Lamoriello had been the GM overseeing most of Komarov’s Toronto tenure, and pounced on the banger on July 1st 2018 a few weeks after seizing the Islanders GM duties.
 
The center scored 26 PTS in 82 GP in year one, averaging 13.9 minutes per game. His PTS and time on ice dropped even further in year two after missing time with an injury and being dropped to the 4th line. This contract was terminated in the final year.
 
 
11. Brendan Witt
 

Signed By:	Garth Snow		Position:	D
Date:	2008-07-08		Age July 1st:	34
Term:	2 years		Playoff GP:	0
Total Money:	$6M		Playoff PTS:	0
Cap Hit:	$3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	8.5	42	5	25
Per 82 GP	4.3	82	10	49	15.2

“To me Brendan Witt is what the Islanders are looking to be. He’s tough he plays with a lot of heart, selfless; he’s a good leader in the locker room.”

– Garth Snow

Garth Snow was so eager to retain Brendan Witt that he signed him to this extension a year before the veteran defenseman was set to reach unrestricted free agency at age 34. Witt was never a glutton for point production, deployed mostly in a defensive role. This is a classic example of how sometimes it can be advantageous to wait until after the season to sign your aging pending UFA, adding more data to your decision-making process.
 
By the time this contract started, Witt was at the end of the road. He played just 42 GP, averaging 15.2 minutes per game, before clearing waivers and getting sent to the AHL. At the end of year one, Garth Snow bought out the remaining term.
 
 
12. Trent Hunter
 

Signed By:	Garth Snow		Position:	F
Date:	2008-02-22		Age July 1st:	27
Term:	5 years		Playoff GP:	0
Total Money:	$10M		Playoff PTS:	0
Cap Hit:	$2M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	13.7	133	63	343
Per 82 GP	2.7	82	39	211	15.3

“Everyone in our organization, and I’m certain our fans, are thrilled Trent Hunter is going to be a New York Islander for at least five more seasons.”

– Garth Snow

Trent Hunter was on his way to becoming an unrestricted free agent in 2008 when Garth Snow decided to take him off the market with a 5-year extension. Hunter would finish the season with 41 PTS while averaging 18.2 minutes per game, which should be worth at least $4M (adjusted) for a 28-year-old on the UFA market.
 
While it did start off on a decent note, this took a dramatic turn into the shitter as his 30th birthday grew closer. By year three, Hunter scored 4 PTS in 17 GP before being traded to New Jersey for another bad contract and then bought out.
 
 
13. Cal Clutterbuck
 

Signed By:	Garth Snow		Position:	F
Date:	2013-07-08		Age July 1st:	25
Term:	4 years		Playoff GP:	18
Total Money:	$11M		Playoff PTS:	6
Cap Hit:	$2.8M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	13.1	292	78	491
Per 82 GP	3.3	82	22	138	13.2

"The fans will love him."

– Garth Snow

The Islanders acquired Cal Clutterbuck in a trade with Minnesota in 2013 and locked him into a 4-year extension one week later. It came at a slightly cheaper price tag than the one that followed, producing similar results (with the exception of generating a higher shot volume when Cal was younger).
 
Shuttlebuck was paid at the rate of a 30-40 point player, and didn’t have any recent comparables in the same scoring-usage range who received even close to this much money. This wasn’t quite as bad of a cluster-f**k as the next Clutterbuck contract, but still should have been at a cost of $1.5M or less (adjusted for cap inflation).
 
 
14. Shawn Bates
 

Signed By:	Mike Milbury		Position:	F
Date:	2006-03-06		Age July 1st:	31
Term:	3 years		Playoff GP:	0
Total Money:	$3.6M		Playoff PTS:	0
Cap Hit:	$1.2M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	6.0	50	10	50
Per 82 GP	2.0	82	16	82	12.3

“Shawn is the kind of versatile and dedicated player that every team in the NHL wants. In a skater's game, he has become even more valuable."

– Mike Milbury

Shawn Bates earned himself a 3-year extension at age 31 after scoring 15 goals and 34 PTS in 66 GP in 2006. He would never again come close to that point total. Under this contract, the center played 50 games and scored 10 PTS. A plethora of injuries did contribute to his demise, but he was also ineffective when healthy (if indeed he ever was). 
 
I’m not about to give Mike Milbury the benefit of the doubt, and will just assume that because he autographed this transaction that it must have been a flawed decision. It’s a safe assumption to make. Garth Snow would later buy out the final year once Bates was presumably healthy.
 
 
15. Jaroslav Halak
 

Signed By:	Garth Snow		Position:	G
Date:	2014-05-22		Age July 1st:	29
Term:	4 years		Playoff Wins:	3
Total Money:	$18M		Playoff SV%:	0.926
Cap Hit:	$4.5M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	5.2	177	88	2.69	0.913

"I'm 29 years old and I know what it takes to be a No. 1. I want to prove myself to everyone that I can be a No. 1."

– Jaroslav Halak

Jaroslav Halak had a strong season in Washington with 29 wins, 13 losses, and a .921 SV% before he was scheduled to become an unrestricted free agent at age 29. The Islanders traded a 4th round pick to acquire his negotiating rights (a draft pick that became future goalie phenom Igor Shesterkin), inking Jaro to this extension a few weeks later. 
 
Jaroslav was eager to prove to the hockey world that he was a legit #1 starter, but really only established himself as a sometimes decent 1B. By year three the Slovakian gatekeeper found himself playing 27 games in the AHL. When this was over, Halak would depart for Boston and kick off a strong career as an often-used back-up.