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10 Worst Contracts of the Decade

by chewy 25. November 2009 09:42

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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