In a salary cap world, bad contracts can significantly hurt a team?s chances at continual improvement both through trades and free agent signings. With 23-man rosters, compared to the 15 an NBA team carries with nearly the same cap limit, it is very important for general managers to be smart with their financial decisions. Below are some regrettable contracts that I am sure some G.M.?s would love to take back. Note: In the NHL, a player?s cap hit is the same in every season of his contract, and is the total salary divided by the number of years; or in simple terms, the average salary of the contract. Also, players in the AHL do not count toward their team?s cap. Cap numbers are taken from NHLscap.com. Honourable mentions: David Legwand, Cristobal Huet, Vincent Lecavalier, Jason Spezza, Martin Erat, Kimmo Timonen, Keith Ballard, Rostislav Olesz, Mike Commodore, Jason Blake, Brian Rolston, Tom Gilbert, Jason Pominville Joffrey Lupul (Anaheim): 4 years/$17M, 3+ years remaining, $4.25M cap hit After helping the Ducks to a Stanley Cup in 2006, Lupul?s value was very high. Sadly, he hasn?t eclipsed his 53 points from that season, though did have 46 in 56 games for Philadelphia in 2007-08 that earned him his current extension. He was dealt from Philly to Anaheim in the Chris Pronger deal this past summer after a 50-point season last year. Now, back with the Ducks after being traded for the 3rd time in his young career (which warrants consideration of his locker room demeanor), he only managed 14 points in 23 games before a back injury ended his season ? the first of his 4-year extension. Too bad for the Ducks, who aren?t the ones that gave him the extension, as back injuries rarely ever completely go away. Some forwards he makes more than: Mikko Koivu, Antoine Vermette, R.J. Umberger, Milan Hejduk, Dustin Brown, Eric Cole, Brenden Morrow, David Krejci, Travis Zajac. Jeff Finger (Toronto): 4 years/$14M, 2+ years remaining, $3.5M cap hit Finger was one of the few transactions made by Cliff Fletcher when he was named interim GM of the Leafs after John Ferguson, Jr. was fired and before Brian Burke was hired. This is clearly one of the few regrettable moves by the Hall of Famer (in the Builders category). After posting a +12 with 19 minutes of playing time in 2007-08, Fletcher signed a defenseman that almost no-one had heard of. Last season he played in only 66 games, contributing only 23 points and was a -7. This year he has been much worse and barely plays due to the blue-line additions by Burke (Mike Komisarek, Francois Beauchemin); he has played only 37 games and has 10 points and a -9 rating while averaging 13+ minutes a night. Most fans and columnists keep pleading to send him to the minors to take his contract off the cap. Some defensemen that he makes more than: Johnny Oduya, Alexander Edler, Steve Staios, Matt Carle, Brendan Witt, Colin White, Cam Barker, Matt Greene. Thomas Vanek (Buffalo): 7 years/$50M, 4+ years remaining, $7.143M cap hit The Oilers made the above offer sheet on Vanek in the 2007 offseason, and the Sabres matched it after watching him pour in 43 goals in just his second NHL season. His point total dropped from 84 to 64 in each of the last two seasons, and looks to finish below that again as he only has 23 goals and 47 points this year in 67 games. If the contract was to pay him as a sniper, then perhaps a deal like Phil Kessel?s would have been more appropriate ($5.4M cap hit). Instead, he is taking up almost as much room as Joe Thornton ($7.2M cap hit), Dany Heatley ($7.5M), Marion Gaborik ($7.5M) Lecavalier ($7.7M) and Rick Nash ($7.8M) and I definitely wouldn?t put him in that category as an elite player. He is also earning more than Jerome Iginla ($7M), Ryan Getzlaf and Corey Perry ($5.3M cap hit each), Martin St. Louis ($5.25M), Alexander Semin ($6M next year), Paul Stastny ($6.6M) and Jonathan Toews and Patrick Kane ($6.3M starting next year). Tim Thomas (Boston): 4 years/$20M, 3+ years remaining, $5M cap hit Thomas signed this extension just before the regular season ended last April, and shortly before he won his first (and last) Vezina Trophy. A $5M cap hit seems very affordable for a Vezina winning goalie, but it?s easy to forget that Thomas is almost 36-years-old because this is only his fifth full season in the NHL. Sadly, age appears to have caught up quickly, as he is in the midst of a brutal season; he sports a 15-17-8, and isn?t in the top-10 in any category. Thomas is definitely walking on thin ice when it comes to the starting job with the Bruins, as he has played in 40 games while his ?backup? Tuuka Rask has played in 37 while being first in the league in goals against and save percentage. It was rumored that Philly was interested in him at the deadline, but it would be real hard to find a team willing to take on three more seasons of Thomas? contract for the way he has been playing as he approaches 40. Chris Pronger (Philadelphia): 7 years/$34+M, 7 years remaining, $4.9+M cap hit Pronger was originally drafted way back in 1993 by the Hartford Whalers. And that is why this contract is so bad, the fact that Pronger is 35-years-old and has not even begun his extension yet. Sure, it seems to make perfect sense that in the final two seasons of the deal he will make around $500k each year since he will be 41 and 42, but that doesn?t change the large cap hit that those seasons will carry (unless he retires, which is likely). Quite simply, despite his stellar play this season, he is far more likely to regress every year from here on out, and that is far too large of a hit for a player staring age 40 right in the face. Brian Gionta (Montreal): 5 years/$25M, 4+ years remaining, $5M cap hit While $5M is not an overbearing number, it is simply much more than Gionta deserves in relation to his peers. Getlaf and Perry have a cap hit of $5.325M, and both are 24-years-old.Would you rather have the 31-year-old Gionta at the above cap hit, or 21-year-old Jordan Staal at $4mil per year? It seems that Montreal overpaid for veteran leadership when they courted this 5?7? spark-plug. Yes, he is a good leader, and yes he is a spark-plug, but he has also had more than 60 points only once in his career and that was 2005-06. Shane Doan is also a great leader, but offers more offensively and makes less ($4.55mil cap hit). Or what about Daniel Alfredsson and his $4.875M hit? Gionta should probably be making $3.5M-$4M a season, and while it is not a huge difference, every dollar counts in the salary cap era, and 4 years from now when he is 35-years-old and contributing on the fourth line, this contract will likely bite the Canadiens in the rear. Chris Drury (NY Rangers): 5 years/$35+M, 2+ years remaining, $7.05M cap hit It should be noted that July 2007 features four contracts on this list (Drury, Vanek, Briere, Gomez), as it appears some GMs didn?t have a good plan in place for the new cap era. Drury?s contact was a perfect example, getting paid like a premier player despite never reaching the 70-point mark in his career. Yes, he was a noted playoff performer for Colorado and then Buffalo, but his offensive production has dropped annually since he signed the big contract. In his first season in the Big Apple, he had 58 points, followed it up with 56, and only has 29 points in 70 games with a -14 rating this year as the Rangers look poised to miss the playoffs despite his noteworthy leadership and guile. As seen above, Getzlaf, Perry, Semin, Iginla, Stastny, St. Louis, Toews and Kane have smaller cap hits despite nearly three times the production. Brian Campbell (Chicago): 8 years/$57+M, 6+ years remaining, $7.14+M cap hit There is always a market for a puck moving defenseman, and often team?s are willing to overpay for their services (whether in trade or in contract). Enter Campbell, who had twice reached the 40-assist plateau and was the most sought after free agent in 2008. He had a fantastic contract year with Buffalo and San Jose, compiling 8 goals and a career-best 54 assists for a career high 62 points. He had 45 assists and 52 points in his first year in Chicago, This year he had 38 points in 68 games before his season-ending injury, which isn?t bad, but the contract sticks out now for a couple of reasons. One, is that he is the third best defenseman on the Hawks (after Duncan Keith and Brent Seabrook ? Canadian Olympians), but makes $1.5mil more than Keith and double that of Seabrook. Secondly, because of large contracts like that of Campbell (and Hossa), Chicago is cap-strapped for the foreseeable future, making their ability to make any more additions very difficult. In comparison to his peers, the only defensemen that had a larger cap hit than Campbell this year are Zdeno Chara ($7.5M) and Nicklas Lidstrom ($7.45M) ? both of whom are Norris Trophy winners and team captains. Daniel Briere (Philadelphia): 8 years/$52M, 5+ years remaining, $6.5M cap hit After finishing dead last in 2006-07, Philadelphia tried to spend their way back into relevancy by luring Buffalo?s co-captain with big dollars. True, he was coming off of a career-best 32 goal-63 assist-95 point campaign, but apparently the team failed to see that he never had more than 65 points in any of his 5 full seasons before that. His first year in Philly saw decent production with 72 points, but a staggering -22 rating. Year two he was limited to 29 games because of injury, accumulating 25 points (though he did have 16 points in 17 playoff games). This year, as the younger forwards have taken over as team leaders, Briere?s production has dropped significantly to 47 points in 68 games. Ideally, he is a very talented second line center and first line power play guy, but he is getting paid like an elite player, which he is not. Scott Gomez (Montreal): 7 years/$51.5M, 4+ years remaining, $7.35+M cap hit Gomez was signed by the Rangers almost the same day that they signed Drury, and the result was equally as uninspiring. The difference was, Gomez had a productive offensive career up until that point; he had 70 points as a rookie in 1999-2000 and won the Calder Trophy, was an All-Star, won two Stanley Cups with New Jersey and had another 70-point season and an 84-point season. So while he wasn?t one of the top stars in the game, he was still a productive offensive player who could play on the first line. But since the contract was signed, he dropped from 70 points to 58, and was traded prior to this season to Montreal. From an offensive stand point he looks to have flattened off from where he was last year, with 55 points to date this year. Shawn Horcoff (Edmonton): 6 years/$33M, 5+ years remaining, $5.5M cap hit When Horcoff signed this extension in the summer of 2008, ex-GM Kevin Love declared that ?Shawn has proven himself as one of the premier players in the NHL.? Um, what? Sure, he was coming off a nice season where he had 50 points in 53 games, but the season before that he had 51 points in 80 games and was a -22. His career highs are 22 goals and 73 points from his 2005-06 season, and while solid, those numbers don?t scream ?premier player.? The year after his extension he had 53 points in 80 games, and his season has been far worse with 31 points in 69 games and a -28 rating. For someone who is allegedly a premier player, and was supposed to be ?an integral part of the organization going forward,? it is no wonder the man who uttered those words is no longer the GM, and no wonder why the Oilers are the league?s worst team. Wade Redden (NY Rangers): 6 years/$39M, 4+ years remaining, $6.5M cap hit The Rangers are clearly the biggest repeat offenders for handing out terrible contracts. Redden was never an elite defender, but was always a positive top-4 guy who could quarterback a power play and give you a solid +20 rating. However, in the two seasons prior to this deal, his play slipped drastically, going from 50 points to below 40, and from +35 to +1 and +11. Senators GM Bryan Murray openly tried to deal him, but was unable to do so because of Redden?s no-trade clause. Year 1 in the Big Apple was not pretty for Redden or the Rangers, as he dipped to a 10-year-low 26 points (including a career-low 3 goals), and was a -5 defensively. This season will go down as the worst of his career, as he only has 2 goals and 12 assists with the lowest ice-time ever (17 minutes a night). He makes the same as Dion Phaneuf, barely less than Dan Boyle and Jay Bouwmeester, and more than Mike Green and Duncan Keith. Marion Hossa (Chicago): 12 years/$62.8M, 11+ years remaining, $5.275M cap hit Truth be told, there isn?t a problem with the cap hit that Hossa has ? it is fitting to his play as one of the better two-way forwards in the game and a 40-goal threat. The problem is, he was 30-years-old when the contract was signed. It isn?t likely that he plays out the entire duration of the contract, but what if he plays until he is 38 or 39 even? At that age, everyone?s production drops, and no one is worth over $5M. A fair comparison is Mike Modano: the 9-time 30-goal scorer is now 39-years-old and only has 26 points in 54 games this year, after 46 points in 80 games last year. Will that be worth $5mil? Absolutely not, especially to a team with severe cap issues going forward because of a dynamic young core. Alexei Yashin (currently in the KHL): 10 years/$87.5M, 5+ years of cap hit remaining Yashin could also be featured in the worst trades article if there was one, after ex-Islanders GM and current TV personality Mike Milbury traded Zdeno Chara and the 2nd overall pick (Jason Spezza) to Ottawa for the mercurial forward in 2001. Milbury then promptly signed Yashin to a contract that was absurd at the time and even worse now. The former 40-goal scorer was bought out in 2007, and that buyout was spread out over eight seasons, five of which still remain. Next season the hit is over $4M, while the remaining four seasons are $2.2M. In a salary cap world where every dollar counts, and where a struggling franchise needs every available opportunity to add talent to its roster, the contract and buyout decisions will hamper this franchise (even if it is just $2.2mil) until end of 2014-2015. It isn?t difficult to now see why Milbury is on TV and still not in a front office position. Rick DiPietro (NY Islanders): 15 years/$67.5M, 11+ years remaining, $4.5M cap hit The issue with this contract, like Hossa?s, isn?t the cap hit ? as $4.5M is a good deal for a team on their starting goalie ? it is with the length. Unlike the NFL, all contracts are guaranteed, so you cannot simply cut a player to get out of his contract in the NHL. The question is, what did DiPietro do to earn such an enormous guarantee from his organization? The answer is tough to find. Yes, he did look promising, but not spectacular. The season before this contract, he had a 3.02 goals against average, and only once in his career has he had a save percentage better than .915. His career record is 119-117-29 with a 2.79 goals against and a .905 save percentage; those are average to slightly-above-average numbers. The main problem has been injuries, as he has not been healthy enough over the last two seasons to see if he has improved or not. In March of 2007 he sustained two concussions, and then in the 2008 All-Star Game he hurt his hip. In the following offseason, he underwent knee surgery. In his third game back he had another knee surgery. Last season and this season combined, DiPietro has only appeared in 13 games. The jury is out on how the final 11 seasons turn out. Nick can be reached at [email protected] or on twitter at @nickobergan