Worst NHL Contracts (2006-2017)

What have been the worst contracts in the NHL since 2006? These are only the contracts signed under a salary Cap. Below you will find a worst of the 15 all-time worst salary cap contracts, then year by year worst contracts lists going back to 2006.

Worst Contracts Since 2006 (ranked by total $ spent)

1- Zach Parise, July 4 2012, 13 years $98M: Signed by Chuck Fletcher. He’s now 33 years old with 8 years remaining and has seen his production decline each season since turning 30. Every year he gets older, this contract looks worse and worse. The team can expect a massive cap recapture penalty at the end of this contract, unless they find a cheap excuse to put him on Long-Term Injured Reserve and avoid the penalty. After these Hossa shenanigans, I’m not sure these “future cap recapture penalty” contracts belong on worst contracts lists anymore. Bowman found a loophole.

2- Vincent LeCavalier, July 13 2008, 11 years $85M: Signed by the owners and Brian Lawton. LeCavalier isn’t even in the league anymore and this contract should have 3 years remaining. Instead it was bought out in year four. He had some trouble staying healthy after turning 30, but that shouldn’t be a surprise when giving an 11-year contract to a 29-year-old. GM Jay Feester quit two days before this contract was signed, citing that Brian Lawton and the owners were now running the team. Did he leave rather than offer LeCavalier this contract?

3- Rick Dipietro, Sep 12 2006, 15 years $67.5M: It could be argued that this contract is only bad because DiPietro could not stay healthy. At the same time, he had a 3.00 GAA and .900 SV% the year before signing this. 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.

4- Brad Richards, July 2 2011, 9 years $60M: Signed by Glen Sather. Richards was quasi productive for the first two years then dropped to 50 PTS in year three at age 33 and was bought out. You shouldn’t give contracts like this to 30 year old players. As much as the Rangers love burning money, you can’t do this in a salary cap world.

5- Daniel Briere, July 1st 2007, 8 years $52M: Signed by Paul Holmgren. This one ranks pretty high on the “what exactly were you thinking” scale, with an AAV that adjusts to $9.4M accounting for cap inflation. An 8-year contract at 29 years old is a big risk. He peaked at 72 PTS under this deal, declining to 16 PTS in 34 GP in year six before being bought out.

6- Scott Gomez, July 1st 2007, 7 years $51.5M: Signed by Glen Sather. He scored 70 PTS in year one and it was pretty much all downhill after that. What’s worse is when you account for the smaller cap in 2007, this AAV is more like $10.5M, which is even more ludicrous. There should be more conspiracy theories about how Sather managed to trade this albatross to Montreal for Ryan McDonagh. Did the Montreal GM lose a bet? Was there blackmail involved?

7- Ilya Bryzgalov, June 23 2011, 9 years $51M: Signed by Paul Holmgren. He played 110 games for Philly before being bought out after year two. Don’t feel bad for Ilya though, he’ll be collecting $1.6M per year until 2027. Human beings will probably set foot on Mars before Ilya’s Flyers cheques stop coming…

8- Bobby Ryan, Oct 2 2014, 7 years $50.7M: Signed by Brian Murray. If he made $4M AAV I’d be thrilled to have him on my team. That’s just too much money. He had some big moments in the 2017 playoffs, but that’s not worth $7M AAV…not even close.

9- Wade Redden, July 1st 2008, 6 years $39M: Signed by Glen Sather. Correct me if I’m wrong, but Wade Redden should be the highest paid player in AHL history (injury rehabs notwithstanding). I sure hope he paid for every single road meal that AHL team ate. He went from 38 PTS the year before signing the contract, down to 26 PTS in year one, 14 PTS by year two, AHL by year three. He wasted away the last good years of his career in the minors so his crazy contract wouldn't count against the salary cap.

10- David Clarkson, July 5th 2013, 7 years $36.7M: Signed by Dave Nonis, traded to Columbus by Dave Nonis for another bad contract. He missed last season due to injury, but it was still a terrible contract prior to the injury. He was crushed my monstrous expectations. It was unfair to expect him to replicate his career year.

11- Chris Drury, July 1st 2007, 5 years $35.25M: Signed by Glen Sather. In year one of the contract his point total fell by 11 from the previous season. By year three he dropped to 32 PTS, year four just 5 PTS, and there was no year five. That cap his was more like $10M AAV in today’s numbers when accounting for cap inflation. Boy Glen Sather's name sure pops up a lot on this list!

12- James Wisniewski, July 1st 2011, 6 years $33M: Signed by Scott Howson. Wisniewski had one good season under this contract before eventually being bought out. It’s one of the best examples of over-paying for an offensive specialist being a failure.

13- Nikolai Khabibulin, Aug 5 2005, 4 years $27M: Signed by Dale Tallon. Do the Blackhawks get Patrick Kane if they don’t sign Khabibulin? I’m not sure you change anything with the time machine. Remember that this was signed under a $39M salary cap with a $6.75 AAV (which is about $12.4M in 2017). Posted a 2.81 GAA and .904 SV% over these 4 seasons.

14- Mike Komisarek, July 1st 2009, 5 years $22.5M: Signed by Brian Burke, bought out July 2, 2013 by Dave Nonis. There should be a cap on what big, slow defensemen get paid. Granted if you needed to make a splash on defense in the summer of 2009, the options were limited.

15- Mike Commodore, July 1st 2008, 5 years $18.7M: Signed by Scott Howson. Another Blue Jackets buyout, this time for a player drastically overpaid for being a Stanley Cup champion. He was quasi respectable in the first year of the contract before starting a downward spiral. If Howsen was trying to make a big splash after replacing Doug MacLean, he landed face first in an empty pool.

Historical Worst NHL Contracts:

2019: Winner: Milan Lucic, runner-up: Brent Seabrook

2018: Winner: Zach Parise, runner-up: Bobby Ryan

2017: Winner: Bobby Ryan, runner-up: Zach Parise

2016: Winner: Andrew Ladd, runner-up: Zach Parise

2015: Winner: David Clarkson, runner-up: Nathan Horton

2014: Winner: David Clarkson, runner-up: Jordan Staal

2013: Winner: Roberto Luongo, runner-up: James Wisniewski

2012: Winner: Vincent LeCavalier, runner-up: Scott Gomez

2011: Winner: Vincent LeCavalier, runner-up: Wade Redden

2010: Winner: Chris Drury, runner-up: Scott Gomez

2009: Winner: Chris Drury, runner-up: Scott Gomez

2008: Winner: Rick DiPietro, runner-up: Chris Drury

2007: Winner: Nikolai Khabibulin, runner-up: Derian Hatcher

2006: Winner: Nikolai Khabibulin, runner-up: Glen Murray