20 Worst NHL UFA Contracts Given Out July 1st (2006-2018)

Here are the 20 worst UFA contracts signed on July 1st since the NHL had a salary cap. It's worth noting that the first day of free agency hasn't always been July 1 every year, just mostly. Never the less, the contracts below were all signed on Canada Day. It's one of the most exciting days on the hockey calendar.

1- 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.

2- Scott Gomez, July 1st 2007, 7 years $51.5M: Signed by Glen Sather. He scored 70 PTS in year 1 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?

3- 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. This qualifies as one of the all-time worst contracts in the salary cap era.

4- 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.

5- Ville Leino, July 1 2011, 6 years $27M: Signed by Darcy Regier. He scored 56 PTS the season before signing this contract. In 3 seasons for Buffalo he scored just 46 PTS before being bought out.

6- Loui Eriksson, July 1st 2016, 6 years $36M: Signed by Jim Benning. It seemed odd at the time that the Canucks would add a “big gun” UFA in the off season when nobody had the illusion this team was still a contender. In year 1 he scored 11G, 24 PTS in 65 GP; not worth the $6M AAV it cost.

7- 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.

8- 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.

9- Matt Moulson, July 1 2014, 5 years $25M: Signed by Tim Murray. His 3 seasons in Buffalo have been the three worst seasons of his career. He hasn’t been bought out yet, but he absolutely should be.

10- Jeff Finger, July 1st 2008, 4 years $14M: Signed by Cliff Fletcher, buried in the minors by Brian Burke. There is a conspiracy theory that the team intended to sign a different player and made a mistake. That’s how bad this one was, it has its own thriving underlying conspiracy theory.

11- Martin Havlat, July 1 2009, 6 years $30M: Signed by Chuck Fletcher. He was good for the first 2 seasons under this contract, then hit a wall at age 30 and was eventually bought out.

12- Milan Lucic, July 1 2016, 7 years $42M: Signed by Peter Chiarelli. He was brought in as a guy who could score PTS playing with McDavid and protect him out on the ice. Milan scored 50 PTS in year one, 34 PTS in year two. Now he’s 30 years old with 5 years left on an expensive contract.

13- Nikolai Khabibulin, July 1 2009, 4 years $15M: Signed by Steve Tambellini. Does this belong on the worst contracts list? Khabibulin was instrumental in the Oilers being a terrible hockey team and securing 3 consecutive 1st overall picks in the draft. In that regard, he did return value to the Oilers. He also back-stopped the team to zero playoff games.

14- Andrew Ladd, July 1 2016, 7 years $38.5M: Signed by Garth Snow. They gave a 7-year contract to a 30-year-old player coming off a 46-point season. He dropped down to 31 PTS in 78 GP in year one. He’s a good character guy, but it’s awful to see the large point decline happen right away.

15- Anton Volchenkov, July 1 2010, 6 years $25.5M: Signed by Lou Lamoriello. He played 4 seasons before being bought out. He was never brought in to score PTS, but had dropped down to just 16m per game in the final season. That’s too much money for that many minutes.

16- Jose Theodore, July 1st 2008, 2 years $9M: Signed by George McPhee. I have to imagine if you asked Capitals fans to recount the Jose Theodore years in Washington, you would not get a pleasant response. His regular seasons were slightly below average, and he started 3 playoff games letting in 11 goals (zero playoff wins). When you account for cap inflation, that AAV is closer to $6M.

17- Dave Bolland, July 1st 2014, 5 years $27.5M: Signed by Dale Tallon. The Dale Tallon Summer of 2014 spending spree yielded very few positive results. He only played 80 games over 2 seasons for Florida before they traded a top prospect to unload his contract. He hasn't played since.

18- 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.

19- Jay McKee, July 1st 2006, 4 years $16M: Signed by Larry Pleau. He scored 16 PTS the season before signing this contract, then put up 0, 9, 8 PTS over the first 3 seasons before being bought out.

20- Mark Fayne, July 1st 2014, 4 years $14.5M: Signed by Craig MacTavish. In the 3rd year of this contract Fayne put up decent numbers for the Bakersfield Condors, only playing 4 games for the Oilers.