Top cap-strapping deals in the NHL

As Alex Rodriguez works on his latest record-setting baseball contract, you have to wonder if this deal with the New York Yankees will work out better than the last blockbuster contract he signed with the Texas Rangers many moons ago.

Professional sports contracts can be risky, especially in the NHL, because each team has a limited number of dollars to spend due to the salary cap. In this week's 10 Degrees, we look at the top nightmare contracts.

10. Todd Bertuzzi, Anaheim Ducks

Contract: $4 million this season and in 2008-09

On a team filled with good, young offensive players, Todd Bertuzzi is the highest-paid forward in Anaheim. Even before he suffered a concussion on Oct. 14, it was easy to question this contract. The 32-year-old forward hasn't been a major physical force since the Steve Moore incident, incapable of being the power forward who provided that amazing mix of skill and strength in Vancouver. His 46-goal campaign from the 2002-03 season is a distant memory, considering that Bertuzzi has played just 22 games over the past two seasons. As much as Brian Burke has been a loyal Bertuzzi supporter, the Ducks' GM may regret the deal. Ryan Getzlaf and Corey Perry are both set to become restricted free agents this summer, while the Ducks are strapped with an oversized deal for an underperforming winger.

9. Pavel Kubina, Toronto Maple Leafs

Contract: $5 million per season through 2009-10

How did this happen? In July 2006, Pavel Kubina signed a four-year, $20-million deal with the Maple Leafs as an unrestricted free agent. His career minus-85 speaks volumes about Kubina's defensive ability, and he has scored 11 goals in a season just once in his career. The 30-year-old does have size and is serviceable as a third or fourth blueliner. That's where he is on the Leafs' depth chart, but he's being paid like a top-line player. Contracts like this should keep Toronto's Cup drought alive for seasons to come.

8. Dustin Penner, Edmonton Oilers

Contract: $4.25 million per season through 2011-12

During the offseason, Edmonton had a difficult time landing a big-time free agent. Then, in one desperate move, they offered Dustin Penner a five-year, $21.25-million deal. As we saw in Anaheim, Penner is a good complementary player, possessing incredible size and a decent scoring touch. The Oilers are banking on him to become a dominant power forward; but, at this point, that may be wishful thinking. Penner is on pace to score 12 goals, 17 less than last season. Not exactly what you want from your highest-paid forward.

7. Kimmo Timonen, Philadelphia Flyers

Contract: $6.33 million per season through 2012-13

OK, so the Flyers finished dead last in the NHL last season in goals against and points. So, the solution is throwing Bobby Orr-type cash at Kimmo Timonen? If you think we're exaggerating, keep in mind Timonen's 2007-08 salary would be the highest on 10 other NHL teams. The two-time All-Star is a crafty defenseman with better-than-average skills. He can quarterback the power play and is durable. The downside -- he is undersized and has never helped elevate a team to greatness. Timonen has never been on a team that has won a playoff series and it's unlikely he will ever live up to the huge dollars he is receiving in Philly.

6. Ed Jovanovski, Phoenix Coyotes

Contract: $6.5 million per season through 2010-11

Ed Jovanovski is still a physical presence on the ice and has good mobility and a great shot, but something doesn't add up. Only Steve McCarthy of the Thrashers has a worse plus/minus than Jovanovski. He always faces the other teams' best players; but, so far, the 31-year-old is failing the test. The Coyotes are last in their division and seem destined to miss the playoffs again. The four-time All-Star has a history of injuries, making you wonder how this deal will look in a few years when Jovanovski is older and less durable.

5. Michael Nylander, Washington Capitals

Contract: $4.875 million against the cap per season through 2010-11

To hand out nearly $20 million dollars to a 35-year-old forward who averages less than 20 goals a season seems downright charitable. Nylander has skill and shows flashes of brilliance, but that's it. It's not a coincidence that Nylander changes teams at an alarming rate. The Caps are his eighth stop in 13 NHL seasons. This contract just boosted Alexander Ovechkin's negotiating power, since he is set to become a restricted free agent this summer. For all those Washington fans who were hoping Nylander could get the Caps back to the playoffs, it may not matter. Nylander's teams have gone 1-8 in playoff series over his career, the lone win coming last season with the New York Rangers.

4. Tomas Vokoun, Florida Panthers

Contract: $5.7 million per season through 2010-11

Tomas Vokoun is a solid No. 1 goalie, but is he the player you can count on to win a playoff game, let alone a series? So far, the answer has been "no." Vokoun has never made it past the first round and has just three career postseason victories in 11 starts. With his lucrative deal, you have to wonder what direction he will take the Panthers. The $5.7 million annual figure is more eye-popping when you realize only three goalies (Nikolai Khabibulin, Jean-Sebastien Giguere and Roberto Luongo) make more money this season.

3. Brad Richards, Tampa Bay Lightning

Contract: $7.8 million per season through 2010-11

Any GM would love to have Brad Richards on his team because he's skilled and smart team player. But the former playoff MVP has never had a 30-goal season or a 100-point campaign, and he isn't his team's leading scorer. And at $95,121 a game, it's safe to say most GMs would pass. Two years from now, Richards' huge contract may come back to burn the Lightning because they may not have enough cap room to keep Vincent Lecavalier, one of the game's best players.

2. Bryan McCabe, Toronto Maple Leafs

Contract: $5.75 million per season through 2010-11

The highest-paid Maple Leaf has become a whipping boy for Toronto fans. A series of ugly giveaways and untimely miscues has the former All-Star lacking confidence and searching for answers. On a team that is last in the league in goals against, McCabe is near the bottom in plus/minus. With a no-movement clause in McCabe's contract, Leafs management will have to sit back and digest the remaining four years of the deal, hoping McCabe can find his old form.

1. Zdeno Chara, Boston Bruins

Contract: $7.5 million per season through 2011

The Boston Bruins were hoping Zdeno Chara could do for them what Tom Brady, David Ortiz and Kevin Garnett are doing for their other local pro teams. But Chara has been a disappointment. Last season, he had a hard time being "the man" as the Bruins missed the playoffs. When Boston loses, the 30-year-old defenseman shoulders a lot of the blame, but that's what happens when you make nearly as much money as the other five Bruins defensemen combined.

Chara is on pace for just four goals this season. He had 16 during his last season in Ottawa in 2005-06. Chara hasn't delivered on the Boston power play, either. Despite having one of the league's hardest shots, he has yet to score on the man advantage. Bottom line -- if you're making $7.5 million a season, you need to be a difference maker. Right now, Chara looks more like a No. 2 defenseman, like he was in Ottawa.

ESPN reporter David Amber is a frequent contributor to ESPN.com.