In the spirit of the free agent season with all the signings of high priced free agents, both restricted and unrestricted, we thought it would be a fitting time to throw together a bullet-list of what we deem to be the top 10 worst contracts in the league today. Keep in mind this list is factoring in the return on the investment, and not just the highest amounts.

We all know of at least a few times we’ve read about a signing and thought “what are they thinking?” Sometimes it works out for the GM and the team involved, and they look brilliant etc… Other times it blows up in their faces and we snicker and talk about how we knew it wouldn’t work. This list is detailing the latter of these scenarios, because it’s more fun.

So without further build-up, here is the list from 10th all the way to the #1 worst active contract in the NHL this season:

• 10th-Ed Jovanovski: (age 33) $6.5 million against the cap for a guy who scored 9 goals and 36 points last year while going -15. With 3 years in Phoenix he’s a combined -34. Granted most guys in Phoenix are on the minus side these days, but it’s the high-priced guys who are supposed to change that.
• 9th-Ryan Smyth: (age 33) $6.25 million against the cap. With 26 goals and 59 points last year, Smyth was really just doing what he always does as far as points in the regular season goes. Widely regarded as a playoff warrior, you’re not going to get return for Smyth unless you actually make the playoffs. Obviously making the playoffs hasn’t been the Kings forte in recent years.
• 8th-Daniel Briere: (age 31) $6.5 million against the cap. After a career season in 2006-07 with 32 goals and 95 points with the Sabers, the Flyers signed Briere to an eight-year, $52 million contract with a no-trade clause. The 72 points in the first year of the contract was a bit of a letdown for the Flyers, but last season he only managed to play 29 regular season games, recording 11 goals and 25 points while battling injuries. The little guys excelled in the post-lockout NHL, where every  infraction was called to open up the game. We all knew it was “over-correcting”, that the powerplays would slow down as the players figured out the new rules and how to defend effectively within them. Less powerplays and open ice means less points for Briere.
• 7th-Dustin Penner:(age 26) $4.25 million against the cap. After a great rookie season in Anaheim where Penner netted 29 goals and 45 points, helping to win the first Stanley Cup in franchise history,  playing with emerging stars Corey Perry and Ryan Getzlaf. Penner was signed to an offer sheet while restricted when the Ducks where too slow to re-sign him. When Kevin Lowe of the Oilers offered 21.25 million over 5 years, Brian Burke of the Ducks publicly criticized Lowe and let Penner go rather than match the offer. With 17 goals and 37 points last season, Penner was publicly criticized by head coach Craig MacTavish for a lack of fitness and competitiveness after being made a healthy scratch for the second consecutive game.
• 6th-Ryan Malone:(age 29) $4.5 million against the cap. For a team with well publicized financial issues, the Tampa Bay lightning, this contract was a head scratcher from the moment it was announced. Front loaded at 6 million for the first 3 years starting last season, the seven year deal totals 31.5 million and concludes in the summer of 2015. Now, nobody is questioning weather or not Malone is a commodity worth having with an ability to score and toughness to spare, but 4.5 million average salary for 7 years with 22.6 goals per season average? A Comparable player is David Backes in St Louis who had 31 goals and 54 points for 2.5 million last season.
• 5th-Jason Blake:(35) $4 million against the cap. Entering the 3rd year of a 5 year deal signed by former Toronto Maple Leaf GM John Ferguson Jr totaling 20 million, Jason Blake has 40 goals in the 2 seasons he’s played in Toronto, ironically matching the 40 he netted for the Islanders in his last season playing there, resulting in the contract he now enjoys. It should be noted that Blake has had health issues (a rare but treatable form of cancer- chronic myelogenous leukemia) and has played as hard as anyone could expect under the circumstances, but to pay a 33 year old like a 40 goal guy when he only did it once (his previous high being 28) was ridiculous. For his part, Blake tried to score with over 300 shots on net in his first year of the deal, but was only able to score 15 goals and Ferguson Jr was replaced by Cliff Fletcher as in term GM in Toronto.
• 4th-Wade Redden:(age 32) $6.5 million against the cap. After spending a decade in the Canadian Capital city of Ottawa, Redden had impressive regular season numbers. With career highs in goals being 17 (12 on the PP) in 2003-04, followed by 50 points after the lockout, Redden was a plus 159 and an anchor on the blueline for the Senators. The problem for the Rangers is that good numbers in Ottawa are largely dependant on being on the ice with the top line of Heatley, Spezza, and Alfredsson. Last season for New York he only managed 3 goals for 26 points, a -5 and the wrath of the Madison Square Garden Faithful. On the bright side, only 5 more years…
• 3rd-Chris Drury:(age 32) $7.05 million against the cap. Drury has consistently put up decent numbers in his career, with 37 goals and 69 points being his highest totals in 2006-07 with the Buffalo Sabers. That said, decent numbers don’t get you 35.25 million over 5 years without the help of Ranger GM Glen Sather. In the first 2 years of this deal Drury has 47 goals and 114 points in the regular season, while earning 14.2 million in 163 games. That’s $123 684 per point,  with an almost million dollar raise coming for the next 2 seasons. You would think this would make him untradable but our next contract proves nothing is impossible. Sorry to Rangers fans but there is a trend here.
• 2nd-Scott Gomez:(age 29) $7.357 million against the cap. After recording 13 goals and 60 points for New Jersey in 2006-07, once again Glen Sather Over-paid to land Gomez in a signing that bordered on insane. With all due respect to Gomez, we’d all take the money, Sather gave him 51.5 million over a seven year period starting the same day as the above mentioned Chris Drury. What was the plan here? Now they had 2 smallish centers making first line money, totaling 14.407 million in the salary cap era. As amazing as this blunder on Sather’s part is, somehow Bob Gainey in Montreal was crazy enough to trade for this contract, showing that really nothing is impossible.
• 1st-Rick DiPietro:(age 27) $4.5 million against the cap. On September 12, 2006, DiPietro signed a 15-year, $67.5 million contract with the Islanders, the longest official NHL contract ever to be signed. Since then, DiPietro has battled concussions as well as hip and knee surgery.  Although Dipietro is a good goaltender this is what everyone was wondering about when he signed a 15 year deal at 25 years of age. Aside from Martin Brodeur and very few others, goaltenders rarely have this kind of longevity or consistant success. You need only look to Anaheim and JS Giguere, 2 years after winning the Stanley cup, losing his starting role to Jonas Hiller. There’s something to be said for not being too comfortable with your position within a franchise. Knowing you’re set for 15 years  professionally, as well as the rest of your life financially, is a good breeding ground for apathy.

So there you have it. I’d like to add an honourable mention to a couple that just missed  making the cut:

• Dany Heatley-Ottawa-Signed 6 year, $45 million deal before last season and after making 10 million last year, requests a trade. Nearly impossible to achieve and with his 4 million signing bonus paid out on July 1st, Ottawa is already in for the “small blind” and will likely play the hand out for this year.
• Anze Kopitar-Los Angeles-Signed a 7 year, $47.6 deal as a restricted free agent. He might be worth that one day but at 21, it’s way to early to tell. Maybe give the kid something to work for in the future before giving him a boat load of money? Too much too soon…

The worst all time contract could be The Islanders signing of Alexei Yashin, or maybe the $20 million for 2 years offered to Mats Sundin by the Canucks last season, but we’ll need to do a list of all time worst contracts to make sure we give credit where it’s due.