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It's not hard to look up and down the rosters in the NHL and identify a handful of contracts that each team would like to take back. This past decade saw a ridiculous jump in the amount of money and term being handed out to players as GMs try to woo the top free agents to their market. While a number of these bad deals ran wild in the era of free spending, the salary cap didn't put an end to the madness by any means. "Cost certainty" doesn't ensure sanity when it comes to individual deals, particularly handed to free agents in July.

As we continue to look back on the past 10 years, let's stop and tip our hat to the worst contracts of the decade.

10. David Legwand (NAS) - 2007 - 6yrs @ 4.5m
In December of 07, the Predators were worried about losing one of the faces of their franchise to free agency the following summer, so they dished out a 6 year deal, worth $4.5 million a year. While the money isn't as ludicrous as others on this list, the Predators overpaid big-time for a guy who's best season (by far) saw him reach 63 points. I recall when Lemieux first made this kind of money in the mid 90's, and now it's being handed out to a 2nd or 3rd line forward. Legwand is on the books until 2014.

9. Wade Redden (NYR) - 2008 - 6 yrs @ 6.5m
$6.5 million dollars per year. That's what the Rangers owe Wade Redden, who is just 2 years into this colossal deal and currently sits about 3rd or 4th on their depth chart for defensemen. It's a good thing the players ahead of him are working on entry level deals, otherwise, the Rangers would be completely out of luck. Redden is still a good defenseman, but the Rangers were desperate to make a splash that summer, and choose the wrong way to go about it. He's actually being paid $8 million this season (more than Gaborik and more than Lundqvist.) They'll be paying on this deal until 2014.

8. Ryan Malone (TAM) - 2008 - 7 yrs @ 4.5m
While the Penguins were sad to see Malone go after he helped get the team to the finals in 2008, there was no way they were coming near matching the silly deal that Tampa threw his way when free agency struck. This was just one of about 10 stooge moves put on the books by the Lightning that summer, but it was by far the worst. Currently, Malone is doing his best to justify the deal, with 14 goals in 21 games. If he can keep this up, he'll work his way off this list. I'm not convinced he will. As Stamkos and Hedman grow out of their entry level deals, and the Lightning are still stuck with Lecavalier's beastly contract, this one will come back to bite them.

7. Michael Handzus (LA) - 2007 - 4 yrs @ 4m
While he didn't break the bank, particularly for a team that isn't paying to the salary cap yet, four million a year is a buttload of cash to pay a guy who is best characterized as a checking center who can occasionally contribute on offense. In 11 NHL seasons, he's averaged about 1/2 point a game. That's too much money for the offensive numbers a decent defenseman can provide.

6. Bobby Holik (NYR) - 2002 - 5 yrs @ 9m
Five years at nine million per year. Holik's contract was the poster child for what was wrong with the NHL, pre salary cap. Throughout his tenure in New York, Sather was infamous for writing blank checks to the best free agents on the market. Fortunately for the Rangers, they were able to buy out the last two seasons on this deal before the salary cap came into play. Had this deal been struck today, it would be one of the worst of all time. Since it happened pre-lock out and had little consequence for the Rangers, we'll settle it in at 6th.

5. Danny Briere (PHI) - 2007 - 8 yrs @ 6.5m
Some deals look worse in retrospect. This one stunk at the time and hasn't gotten any better. Particularly with the talent already occupying the top 3 lines in Philly, the Briere contract has been a burden since the day it was done. Briere has yet to rise above being a 3rd line center in Philly and he's being paid way too much for what he brings. If the deal were shorter, he could have been dealt, but as it is, the Flyers are stuck with this lousy deal for another 5 years.

4. Brian Campbell (CHI) - 2008 - 6 yrs @ 7m
In the summer of 2008, the Blackhawks were a team on the rise. They patiently built up a quality roster of up and coming stars, and were poised to become a power once again in the NHL. Then, out of nowhere, they jumped into the Brian Campbell sweepstakes in an attempt to create some noise. In the process, they all but ensured the collapse of the team before they even arrived. The Hawks already boast one of the best defenses in the league and really don't need Campbell on their roster to win. Nonetheless, they're stuck with it until this monster contract runs out in 2016.

3. Brian Gionta (MON) - 2009 - 5 yrs @ 5m
It's hard to imagine anything Bob Gainey did last summer working out for the good in Montreal, but this deal will be his calling card. 5 years at $5 million a year for Brian Gionta. Most (sane) observers saw Gionta's worth pushing $3m a season, at best last summer. Gainey was so bent on rebuilding his team from the ground up that he was throwing money at whomever was available. Gionta has one good season on his resume. Aside from that, he has the point totals of a third line winger. This deal was dumb.

2. Rick DiPietro (NYI) - 2006 - 15 yrs @ 4.5m
This deal was laughed at even before DiPietro's injury problems started to strike. Wang and Milbury seemed more concerned with reinventing the system and making headlines than with building a successful team in New York. The good news is, they only have to pay on this deal until 2022, about the time DiPietro is celebrating his 10th year in retirement.

1. Alexei Yashin (NYI) - 2001 - 10 yrs @8.7m
This was really a no-brainer for worst contract of all time. It's a shame for Yashin's sake that he was saddled with crazy expectations, but I doubt you'll find many sympathizers. To highlight how bad this deal is, the Islanders will still be taking a cap hit on his contract through 2015. There's a reason Milbury is providing commentary and not running another organization right now.

There were plenty of deals to choose from, and here are a few that get the dis-honorable mention:

Brad Richards (TAM) - 5 yrs @ 8m
Jeff Finger (TOR) - 4 yrs @ 3.5m
Jason Blake (TOR) - 5 yrs @ 4m
Pavel Kubina (TOR) - 4 yrs @ 5m
Vincent Lecavalier (TAM) - 11 yrs @ 7.7m
Michael Nylander (WAS) - 4 yrs @ 5m

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Filed Under:   bad contracts   decade review  
November 25, 2009 12:06 PM ET | Delete
no mention of gomez or drury? One of those two belong on that listhow bout rolston in NJ (bust so far)zubrus in NJ comes to mind also
November 25, 2009 12:34 PM ET | Delete
Honestly, no mention of Gomez and Drury means this list isn't close to being right. Also, the Briere contract is bad, but at the time, Carter and Richards were not exactly coming off great seasons and were no sure bets.
November 25, 2009 12:49 PM ET | Delete
Erat! No better than Legwand and being paid more.
November 25, 2009 1:16 PM ET | Delete
I feel like just about anyone mentioned from the Rangers (Drury, Gomez, Rozsival) is worse on the books than Ryan Malone.Which observers were counting on Gionta making 3m? because I can't imagine him earning much less than 4 and change on the open market. He's a proven scorer. Those generally attract interest... see Kovalev, Alexei for another example.
November 25, 2009 1:21 PM ET | Delete
November 25, 2009 1:32 PM ET | Delete
Handzus shouldn't be on the list (not that its a good contract) and from a personal stand point: Redden needs to be somewhere in the top 5, if not 3
November 25, 2009 2:29 PM ET | Delete
well done, shame on you fukers that just complain
November 25, 2009 2:34 PM ET | Delete
Considering how his career went, I would think Mike Rathje should be in there somewhere
November 25, 2009 3:11 PM ET | Delete
Bryan McCabe, 5 years @ 5.75M
November 25, 2009 4:08 PM ET | Delete
Cristobal Huet... Scott Gomez... Chris Drury... Shawn Horcoff... Roman Hamrlik... JS Giguere... Ryan Smyth...
November 25, 2009 5:27 PM ET | Delete
darius kaspariatius's contract was terrible too.
November 25, 2009 5:33 PM ET | Delete
Redden should be much higher, if not in the top 3. No Rozi, Gomez, Drury? Kasparitis could have made the list too... its sad Sather had to do with SIX horrible contracts (gaborik seems to be worth it... so far).
November 25, 2009 9:40 PM ET | Delete
I don't know how you can have contract's listed in the top 10 of the DECADE where the ink is barely dry on the paper. How do you know these players are completely gonna crap the bed? Are you Biff Tannen?
November 25, 2009 11:33 PM ET | Delete
yea... u lost ur credibility by picking briere's contract over gomez' and drury's... in that UFA year i would pick briere over those two any day!
November 25, 2009 11:52 PM ET | Delete
Briere isn't a 3rd line Center for the Flyers. He's played wing all year. Need to get the facts straight.
November 26, 2009 12:17 AM ET | Delete
Gionta is being played top-player money and seemed to be delivering on the goods before injury. Ballsy but not bad... yet.Gomez however is a terrible deal, polying 7years at more than 8mil on a 60 point player. Jason Blake wasn't a great investment either, having been locked up till the end of time for 5mil, and Christobal Huet is a terrible payscale.
November 26, 2009 12:36 AM ET | Delete
How can a 60-65 points forward be only 3M worthy? Take a look around the league and you will find out that a veteran who is a 60-65 points player will earn 5M a year, or near that.Welcome to 2009.PS : You should have named Gomez.PS2: No way you should name Malone right now.
November 26, 2009 3:34 AM ET | Delete
Richards Gomez Drury Finger need to be higher up
November 26, 2009 12:54 PM ET | Delete
Disagree on the Briere deal. In his first year with the Flyers they went to the conference finals. That is not a disappointment. I think some other deals mentioned above have that one beat badly. Great post!
November 26, 2009 3:41 PM ET | Delete
Brieres contract only looks bad if you look at the fact he missed most of last yer but really year 1 - 79 GP 72P - 17PO Games 16 points.. Year 2 -29GP 25P, 6 PO games 4 P.. this year 17G 16P.. how is that really bad?
November 26, 2009 10:05 PM ET | Delete
November 27, 2009 12:35 PM ET | Delete
Message Posted
November 27, 2009 12:35 PM ET | Delete
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November 27, 2009 12:36 PM ET | Delete
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November 27, 2009 2:29 PM ET | Delete
Lecavalier? Horcoff?
November 28, 2009 3:34 PM ET | Delete
Redden's contract is worse than Yashin's... Yashin is no longer a major issue for anybody. Sure, it was a stupid deal, but the Isles needed a franchise building block and nobody can deny Yashin had very productive seasons in Ottawa. Redden was already on the decline when the Rags signed his sorry ass...
November 28, 2009 3:47 PM ET | Delete
What about Shawn Horcoff making 7 mil this year with a 5.5 mil cap hit til 2015.
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