There are enough bad contracts out there to make a top 30 list. Some honourable mentions; James Wisniewski, Zybnek Michalek, David Jones (just signed), Mikael Grabovski, Ales Hemsky, Tom Plekanec, Tom Kaberle, Mike Cammalleri, etc. Here are the top 15.
1) Vincent Lecavalier, TB: 9 more years at $7.7M - #1 on this list last season, he did nothing to play his way out of the top spot, and his contract is still obscene. He's still an above average player with a Stanley Cup ring, but with $62M remaining over the age of 31 is too much no matter how you look at it. $7.7M will buy you about 65 GP and 50 PTS, expensive PTS to put it mildly.
2) Scott Gomez, MTL: 2 more years at $7.4M - Amnesty clause or not, he will be bought out before the start of the next NHL season. One of the worst contracts ever signed (next to Bobby Holik), the only reprieve being it's not 9 more years. Between Gomez, Holik, and Redden, Glen Sather has his signature on some of the worst contracts in NHL history. Who is next on the list?
3) Wade Redden, NYR: 2 more years at $6.5M - New York can't afford the cap hit of a standard buyout, but if there is a new CBA amnesty buyout, Wade could get paid $10M+ to become a free agent. He's an NHL caliber player at too heavy a price. Because the Rangers buried him in the AHL, we don't have a recent NHL sample for his salary to be compared to, except his 14 PTS in 75 GP in 2010. If my memory serves me correctly, he really sucked that season.
4) Mike Komisarek, TOR: 2 more years at $4.5M - Dead weight, and a likely candidate for an amnesty buyout. His no movement clause prevents Toronto from hiding him the minors like they did with Jeff Finger. In a world where Toronto is jammed up against the salary cap, this contract hurts. He provides virtually no offense while being big and slow. He's not the same player that he was in Montreal, he's been getting progressively worse and might be out of gas by age 30.
5) Ed Jovanovski, FLA: 3 more years at $4.13M - This contract could become a case study for how low income teams can circumvent the salary floor. Sign long contracts with players 35+, and when they retire the cap hit remains while the team no longer has to play the player. Florida would probably rather Jovo retire with a cap hit than have to play him and pay him. It was a great career, but Jovo Cop has nothing left.
6) Ilya Bryzgalov, PHI: 8 more years at $5.6M - Mr Universe had a bad year. The cap hit is reasonable if he can bounce back, but right now Mr Snyder can't be feeling very happy about this contract (especially considering they shipped Carter and Richards out of town to make room for it, two players who just won the Stanley Cup). Perhaps Philly should offer Sean Burke $20M to be their goalie coach? Losing his personal coach might be a contributing factor to the struggles Bryzgalov this season.
7) Shawn Horcoff, EDM: 3 more years at $5.5M - That's a lot of money to spend on 34 PTS and a -23. Edmonton signed him to a 6 year deal in 2009, and his production dropped by 17 PTS the following season. He regressed immediately after signing the contract and has not recovered. Now he's 33 years old with 3 years left at a price he's nowhere near worth. It was a front loaded contract, which just makes the first 3 years of the deal look all that more worse.
8) Ville Leino, BUF: 5 more years at $4.5M - Buffalo, this was too much, too late. He scored just 25 PTS in 2011/12 after 52 PTS the year previous. He had a career year in Philly and Buffalo overpaid for production unlikely to be repeated. In 2012 Leino was closer to his 2010 total of 11 PTS than he was to his 52 PTS in 2011. Buffalo had to pay him $6M this year, and $6M next year. He's 28 years old and has a shot at earning some of that money, but he sure didn't this season.
9) Roberto Luongo, VAN?: 10 more years at $5.3M - The term is the biggest killer with this contract, as the veteran emotionally unstable goaltender is being run out of Vancouver. He's got a few good years left in him, but if he decides to play an extended career, buyer beware. Thank you Roberto for winning that gold medal for Canada on Canadian soil; but as a Vancouver resident who watches many Canuck games, I've seen far too many meltdowns to invest $53M in this over 30 goaltender.
10) Paul Martin, PIT: 3 more years at $5M - Paul Martin had a bad year, proving especially easy to score on, a bad quality for a top 4 D man. The Penguins D were by far the weakest link on this team with Stanley Cup expectations, and this contract makes it difficult for a small budget team like Pittsburgh to re-tool its blueline (an honourable mention to Zybnek Michalek, 3 years at $4M, compounding blueline problem). Interestingly enough, Paul Martin has never missed the Stanley Cup playoffs in his 9 year career, though he's also never been past the 2nd round.
11) Andrei Markov, MTL: 2 more years at $5.75M - Normally I'm against ranking a contract as among the league's worse because of an injury; in this case Montreal knew exactly what they were getting when they offered him this deal. Markov has had so many surgeries now that it is impossible to trust that he'll ever play a complete season again. He's an elite D-man if he can ever get healthy, that's just not something I'd like to wager several million dollars on.
12) Keith Ballard, VAN: 3 more years at $4.2M - A change of scenery might be all it takes for Ballard to play his way back into respectability, but that won't happen while Alain Vigneault is his coach (and coach V has been extended). The biggest knock on him is that he's mistake prone, which can be costly. He had 28 PTS in 82 GP for the 2010 Florida Panthers, and has scored 15 PTS in 126 GP for the Vancouver Canucks. He's not the same player that he was in Florida, which makes you wonder what the Panthers knew when they decided to trade him to Vancouver. Bouwmeester also experienced a similar decline after leaving the hapless Panthers. Who's next on the list?
13) Jay Bouwmeester, CGY: 2 more years at $6.8M - J-Bo is a good player, but he's being overpaid by about $2M annually. He has two active streaks leading the NHL, the current ironman streak on the bright side, and the active leader of NHL GP without playing in the playoffs on the dark side. Neither are all-time records, but he is the active leader in both categories. He never played a playoff game in the WHL either. Is he just unlucky to find himself on bad teams, or is he one of the reasons the team is bad? My final ruling on Bouwmeester, good enough to play top 6 D on any team, but he's not worth what he's being paid.
14) Alex Ovechkin, WSH: 9 more years at $9.5M - He's still among the most dangerous scorers in the league, but considering his rate of decline the last 3 seasons, that term at that price is officially an albatross. He's a $6M player at best and if his body is already starting to wear down, it could be a product of the high velocity, high impact style that he plays. Ergo, 9 more years could have disastrous consequences. Perhaps he'll score 100 PTS next season and make me look foolhardy. Then again, you can score 100 PTS and still make a worst contracts list...
15) Ilya Kovalchuk, NJ: 13 more years at $6.6M - It may seem strange for a player who scored over 100 PTS in the regular season and playoffs to make a worst contracts list, but this is a contract that should be illegal in a salary cap world. The Devils have to pay him $11M for the next 5 years, which is a lot for a team having financial difficulties. Perhaps he won't play up to the age of 42, but the minutes this guy logs, he's going to start running out of gas sooner rather than later. He's owed $79M over the age of 30 (peak production tends to occur near age 27). Maybe the joke is on us an Ilya will retire at age 34, which just goes to show you that contracts like this one should be illegal. In the next CBA, all over 35 years "post retirement" should count against the cap even if the contract was signed at age 28 (but has to play to count against salary floor).
Furthermore, Kovalchuk's weak performance in the finals reminds us that when he loses his burst, he's largely ineffective. His back was sore, but every time he touched the puck, he stopped moving his feet and looked to pass. Good thing they played him so much. The sharp shooting Russian nearly played his way off the worst contracts list through the first three round of the playoffs, but it's the 13 year term that does the most damage. If the Kovalchuk contract prevents them from retaining the services of Zach Parise, that's all the more reason this is a bad contract (opportunity cost)...even if he scores a few goals. If Parise leaves town, expect Kovalchuk's production to drop.