10 Worst Contracts In The NHL

August, as always has been a quiet month in the National Hockey League. While some are participating in Olympic training camps for their respective countries, others sit at home and unwind with their friends and family. For Boston forward Phil Kessel, the waiting game continues as he's still without a contract as the Bruins are just 39 days away from taking to the ice for their first game of the 2009-10 season. While it's rumored that Kessel's asking price is preventing the 21 year old from being signed, it's a good time to look at the ten worst contracts currently active in the NHL.

10) Michael Nylander (Washington Capitals) - For many B's die-hards, Michael Nylander is known as the other half of the Bruins trade deadline acquisitions from the 2003-04 season (the other being Sergei Gonchar) and was the Bruins best offensive presence in their seven game series loss to the Montreal Canadiens. In what appeared to be typical shrewd-Bruins-front-office, the B's made no effort to keep the center and let him walk.

After the lock-out concluded, Nylander became a Ranger and put together two solid seasons in Manhattan where he scored 162 points in 160 games, only to jet off to Washington on a four-year deal that paid him 19.5 million dollars over the next four seasons. Nylander has been unable to stay healthy and has found himself a healthy scratch and in Caps coach Bruce Boudreau's doghouse.

Nylander's -19 and dissatisfying 70 points in 112 games for the Capitals truly show how far this Swedish superstar has fallen. With a 4.875 million dollar cap hit through 2010-11, it's likely that Nylander could be in a buy-out situation and jet off to the KHL for a tax-free paycheck and playing time, something he can't find in the nation's capital.

9) Ryan Smyth (Los Angeles Kings) - To be fair to the purple-and-black that reside in California, this signing wasn't the doings of Kings GM Dean Lombardi. However, when Ryan Smyth was signed to a five-year, 31+ million dollar contract by the Colorado Avalanche the eyebrows of NHL fans were collectively raised and for good reason. The question marks behind throwing over an annual salary north of six million dollars for a player who'd only cracked 70+ points one time in his 12 year career seemed to give off the notion that the Av's were in trouble. That was undoubtedly the case and Smyth produced just 40 goals in total throughout his two seasons in Denver.

In a cap space clearing move for a rebuilding club, Colorado sent the sensitive winger out of town where Smyth is hoping to regain his scoring touch in scorer's-friendly Pacific Division with the Los Angeles Kings. He's likely to be playing with Anze Kopitar and Dustin Brown and is looking to reach the 70 point plateau. If he is to continue to falter, his 6.25 million cap hit through the 2011-12 could cripple the Kings development into a solid contender.

8) Chris Drury (New York Rangers) - When the New York Rangers stole away the Sabres captain and vocal leader, the move seemed to be a good one for the blueshirts in their attempt to add veteran depth to complement players such as Jagr, Shanahan and Lundqvist but simply put, this has not been 35,250,000 dollars well spent. Despite Drury's career highs in both goals and points in his final year with the Buffalo Sabres, that success has not transpired into success with the Rangers.

In 2006-07, Chris Drury was simply a force for the Presidents Trophy winning Buffalo Sabres. His 37 goals, 17 of which scored on the powerplay, which are both career highs to this day and leadership propelled the Sabres to the Eastern Conference Finals for the second year in a row, only to lose yet again but this time to the Ottawa Senators. Undoubtedly, the Sabres captain was considered among the top free agents available on July 1st, 2007.

However, what he's brought to the Rangers has been simply disappointing compared to what was expected. In two seasons on Pennsylvania Plaza, Drury has posted a total of just 114 points in 163 games for the Rangers with a -11. Drury's lack of anything offensively comes as a surprise when considering he's led the Rangers in shifts per game and has averaged 3:45 minutes of time on ice on the powerplay in two years in Manhattan.

Drury's current cap hit is at 7.050 million dollars a season and will not be coming off New York's checkbook until the conclusion of the 2011-12 NHL season. Was Drury the best captain 32-million dollars could buy for a perennial bubble-team? Glen Sather apparently thinks so.

7) Jeff Finger (Toronto Maple Leafs) - If this wasn't a desperate measure to keep the fans from completely giving up on the 2008-09 Maple Leafs then I'm not sure what would be? Oh yeah, it'd be actually signing Jeff Finger to this contract.

Heading into the free agency frenzy of 2008, Jeff Finger was coming off a solid season for the Colorado Avalanche where he put up 19 points in 72 games and finished with a +12 from the blue-line. Finger, never really the puck-mover made his living getting down and dirty for the Av's, his 121 hits were tops for the 2007-08 club and his 117 blocked shots were good for fourth on the club. Despite these impressive defensive stats, the coffee mugs of Leafs Nation had to without-question shatter on their living room floors when they saw that Jeff Finger was now a member of the blue and white with a four-year contract worth 14 million dollars.

The Finger era in Toronto began in 2008-09, as the 29-year old Michigan native scored 23 points and finished with a -7 on a horrid goaltended team in Ontario. With a contract deeming Finger virtually immovable and the Leafs additions of Exelby, Beauchemin and Komisarek to their blue-line the necessity of Finger simply does not exist. Finger isn't set to come off the Leafs books until 2012, making his contract one of the worst in the National Hockey League.

6) Joffrey Lupul (Anaheim Ducks) - What do Michael Ryder, Brad Boyes, Ales Hemsky and Johan Franzen all have in common? They all make less money than Joffrey Lupul. What do these players also have in common with Joffrey Lupul? They all finished with more points than him in 2008-09. Joffrey Lupul provides great secondary scoring on any club, and that's not really a topic for discussion, but is his production really worthy of 4.25 million dollars a year until 2013?

That question is answered by a simple no considering he's career high in points came in 2005-06 with the Ducks (53). However, in what has seemingly become Flyers-ritual, Lupul was awarded with a monstrous contract well above his market value in order to keep the Alberta native in Philly.

Lupul was sent back to Anaheim in a deal where the Flyers acquired Chris Pronger (only to give him a ridiculous contract as well) and is now officially on the Ducks cap until the conclusion of the 2012-13 NHL season. With guys like Bobby Ryan, Jonas Hiller, Teemu Selanne and Saku Koivu up for new contracts at the end of this upcoming season, Lupul's contract could hinder the Ducks from being able to re-sign their expected-to-be key players.

5) Wade Redden (New York Rangers) - If I were to ever meet Wade Redden, I'd probably ask him how it feels to be the sixth highest paid defensemen in the NHL.

After all, I'm quite sure the answer would be simple considering he's doing close to nothing and earning a 6,500,000 dollar salary from here until 2014. Redden's performance in his first year with the Rangers was simply dismal, his 28 points and -5 weren't even as embarrassing as his team-defenseman high 40 giveaways.

And we thought Ottawa screwed up when they opted to re-sign Wade Redden over Zdeno Chara in the 2006 off-season. Leave it to Glen Sather to once again prove why the Rangers will be forever basking in the glory of the 1994 Stanley Cup, because it ain't comin' back to Manhattan anytime soon with these wildly gross and reckless over-payments of players.

4) Daniel Briere (Philadelphia Flyers) - In your mind, this signing looks to be a phenomenal one for the Flyers, you know why? Because you have the thought of Briere's performance with the 2006-07 Buffalo Sabres embedded in your mind because, well, it was simply a thrill to witness.

When the Quebec native signed an 8-year deal worth 52 million dollars, the idea that the Flyers were on their way to becoming an elite team in the Eastern Conference grew. In 2007-08, Briere didn't disappoint the Flyer faithful as he put up 72 points in 79 games, 37 of which coming on the powerplay. Briere also carried much of the Flyers offense towards their push towards the Conference Finals where he scored 16 points in 17 games.

Injuries struck the 31-year old in 2008-09, as he was held to just 25 points in 29 games. However, it's not the injuries that make this signing so poor, it's the fact that Briere's no-movement clause and annual cap-hit of 6.5 million dollars from now until 2015 really stifles the Flyers ability to add anyone to their roster without having to move a star of equal or greater value. Especially if the Flyers are to continue to develop strong youth players within their organization (Carter, Richards and Giroux to name a few).

3) Brian Campbell (Chicago Blackhawks) - There's no debating that Chicago needed a top defensemen, but a top defensemen for eight years?

Often longer contracts mean smaller cap hits, making the idea of an eight year contract somewhat, loosely plausible. However, Campbell's 7.1 million dollar cap hit is doing nothing but hurting the 'Hawks for years to come. With Patrick Kane, Jonathan Toews, Duncan Keith, Jack Skille, Andrew Ladd and Adam Burish being the top names for players up for new contracts following the 2009-10 season, the idea of Campbell's cap-hit for years to come is simply nauseating for any Chicago fan.

The difficulties are created within the idea that Chicago won't move Hossa after signing him to a 12 year deal and Cristobal Huet is unlikely to get dealt considering there's no one within the Blackhawks system ready to take over as the number one goaltender. When factoring this in, the likelihood of the Blackhawks being able to keep Kane and Toews for years to come grows unlikely. Along with that, the idea of unloading Campbell's contract and getting anything of equal value in return is just as unlikely.

For the Blackhawks, it appears that 2009-10 is either Stanley Cup or bust.

2) Scott Gomez (Montreal Canadiens) - Ladies and gentlemen, one of the most overrated players in the National Hockey League, Scott Gomez.

Continuing with the Glen Sather trend, the idea of Scott Gomez making 51,500,000 over the next eight years almost seems laughable. Here's a player who thrived under a defensive-trap system and was coming off a season where he registered his lowest point total since the end of the league's work stoppage. However, this didn't stop the Rangers front office from over-paying for the crafty powerplay specialist.

Gomez didn't fail to not disappoint during his tenure with the Rangers before being traded to the Montreal Canadiens. Despite Gomez's 40+ assists and 16 goals in both seasons with the Rangers, the stats don't even come close to fitting the price-tag Gomez is marked for until 2014.

Can Gomez be the number one center the Canadiens need or will it be another year of mediocrity in hockey's most demanding city? I'm thinking it'll be the latter of the two.

1) Rick DiPietro (New York Islanders) - Just when you thought the Islanders couldn't be more upsetting to their fans. The signing of Rick DiPietro to a fifteen, yes fifteen year contract is enough to make the stomaches of even the most faithful Isles fans turn.

Taken with the number one overall pick in the 2000 NHL Draft by New York (over Dany Heatley and Marian Gaborik) the hope for DiPietro was that he was going to be the savior for the Islanders franchise and return them to a competitive level in the Eastern Conference. To say things haven't gone as planned would be an understatement.

DiPietro may be 67+ million dollars richer and has another 12 years of guaranteed money, but he's simply doing nothing to help the Islanders as of right now and possibly for the foreseeable future. With the signing of Marty Biron and Dwayne Roloson, it appears that Rick DiPietro will once again be out for the season for the Isles will a knee injury.

Congratulations Garth, your god awful signing of DiPietro will more than likely, actually strike that, will undoubtedly outlive your tenure as Islanders general manager, but your impact to the club for years to come will unfortunately haunt Long Island, or perhaps Kansas City.