The 5 best and 5 worst contracts in the last decade

(No, the first decade of the 21st century doesn't technically end until 2011. Save your bellyaching. But we've had nine NHL seasons and one stolen from us since 1999-2000, and Yahoo! Sports has decided it's time to rank the best and worst of the last "decade." Enjoy, and snark freely in the comments. Today's edition is written by "What We Learned" author Ryan Lambert.)

In the course of researching this list, I came to the realization that this would be a difficult one to cook up. There's never been a decade like this, where half of it was full of insane contracts from three or four teams and the other half was ... well I guess it was also full of insane contracts from three or four teams, but those were under the salary cap and were therefore even more insane.

(Like, for example: Eric Staal's(notes) cap hit of $8.25 million for seven years. Players that make more than that: Alex Ovechkin(notes) at $9.358 until 2021, Sid Crosby at $8.7 million until 2013 and Evgeni Malkin(notes) at the same rate as Crosby until the following year. And that's it.)

So no, I will not be listing things like Martin Lapointe(notes) getting $20 million for four years from the Bruins (and scoring 83 points in three years before getting run out of town on a rail). That was before the salary cap era; and regardless of how terrible the deal was, it was the Wild West and no one really had to care about spending ridiculous money on bad players because there was no punishment for it except on the ice. If you were a team with deep pockets like Rangers, you could spend a billion dollars on a team that didn't make the playoffs as long as ownership didn't mind paying it.

That's why all the "best" contracts are post-cap, and only a few of the worst are pre-cap.

Here we go then: the five best and worst contracts this decade ...

Part 1: The five worst

5. Dustin Penner(notes), Edmonton Oilers

Clearly, Kevin Lowe was looking to make a splash. He tried to sign Tom Vanek to an offer sheet of seven years, $50 million, and he would have gotten away with it too if it hadn't been for those pesky Sabres matching the offer. So Lowe went out and did the next best thing: Signing Anaheim's restricted free agent forward Dustin Penner to a five-year, $21.25 million deal.

What he probably didn't realize was that Penner wasn't that great. As the Oilers' highest-paid forward (until Shawn Horcoff(notes) signed his ridiculous deal this offseason), he scored 84 points over two seasons. While he's showing signs that he's turning it around (15-15-30 through his first 27 games this year), this contract was a symbol of everything that could go wrong under the current CBA.

4. Brian Campbell(notes), Chicago Blackhawks

Back in the summer of 2008, the Chicago Blackhawks thought they were in desperate need of defensive help for some reason. Apparently having a top-three of Brent Seabrook(notes), Cam Barker(notes) and Duncan Keith(notes) wasn't good enough for them. So they got more defensive help from... Brian Campbell?

Yeah, apparently they thought he was a great two-way defenseman that was worth about $58 million over eight years. No, I don't know why. Granted, he scored 62 points in his contract year, playing for both Buffalo and San Jose, but he was still only a plus-8, and that's after going plus-9 in 20 games with the Sharks. And let's just say his postseason track record fit in perfectly with the rest of the boys in San Jose.

Granted Campbell, has put up pretty good offensive numbers in Chicago, but his salary (along with Brent Sopel's)(notes) is the main reason the team stressed over its cap situation before signing Jonathan Toews(notes), Patrick Kane(notes) and Duncan Keith.

3. Wade Redden(notes), New York Rangers

Redden gets escorted out of Ottawa by a group of the local citizenry that had armed itself with torches and pitchforks. That's fine. It happens. And he was, for a little while, one of the better defensemen in the league.

But after Redden came off a 6-32-38 season in 2007-08 (his worst since the ‘90s), the Rangers said, "Hey Wade, we want you on board." And Redden should've been happy with that. Big market, and he probably figured he'd get decent money.

He was wrong. He got obscene money.

His six-year, $39 million deal gives the Rangers a cap hit of $6.5 million through 2014. For a player that has, in his first 105 games in New York, produced four goals, 28 assists and has looked like a turnstile most nights. Don't worry though, Ranger fans. Only four more years of that after this one!

2. Bobby Holik(notes), New York Rangers, then Atlanta Thrashers

Holik got ridiculous money to jump from the Devils to the Rangers in the summer of 2002. I mean, $9 million would have been a lot for anyone, let alone Holik who had a career high of 65 points.

But again, pre-lockout, who cares, right?

Well, the problem for the Rangers was that the contract obviously spilled into the new CBA, and even with the salary rollback they were paying Bobby "freaking" Holik $6.726 million when the salary cap was just -- get this -- $39 million. So they bought him out and then had to pay him another $3.5 million for not playing during the lockout. The Rangers were less than pleased with that, as you can imagine.

He then signed with the Thrashers for a nearly-as-ridiculous $12.75 million, and in return Atlanta got 96 points. It begs the question: Of how many NHL executives does Holik own compromising photos?

1. Alexei Yashin(notes), New York Islanders

You might be thinking that the DiPietro contract is the worst the Islanders gave out this decade, but you're forgetting a contract so hilariously bad that even Glen Sather probably threw his back out laughing when he heard about it.

Ten years, $87.5 million. Biggest in league history. For a player widely regarded to be as lazy as he was talented, and twice as petulant as he was lazy (his holdouts with the Senators are legendary). Sure, he'd been phenomenal in Ottawa; 172 goals in the prior four seasons is a good amount. So maybe he is worth close to $9 million to a New York-based team with a sweet TV deal in the pre-cap world. But 10 years? The guy was 28 when he signed it.

To make matters worse, he was pretty awful on the Island. After potting that 172 in four years, he scored 119 over five with the Islanders (and a whopping five goals in four one-and-done playoff appearances). So the Islanders did the only prudent thing and bought him out.

And they say you can still find the ghost of that contract to this day: haunting the Islanders' cap number to the tune of $3.235 million a year -- still the third-highest cap hit on the team! -- until 2015.

Part 2: The five best

(Keeping in mind these are all post-cap.)

5. Marc Savard(notes), Boston Bruins (x2)

Even before you figure the money on his new deal is ridiculously low commensurate to what he currently produces for the Bruins, you have to look at the contract he's currently on.

In the summer of 2006, Zdeno Chara(notes) put pen to paper on a five-year, $37.5 million deal and 10 minutes later, Savard had agreed to a four-year deal worth $20 million. When he first signed, everyone said, "Oh that might be pretty good." After all, the previous year he had scored 97 alongside Ilya Kovalchuk(notes) in Atlanta and everyone was curious to see if he could replicate it in Boston. In fact, he did better. He put up 96 points that first year with the Bruins, and that was without the benefit of a guy like Kovalchuk anywhere near his line.

The next two years saw him drop off a little, to the tune of 40-126-166 in 156 games. Not bad for five million bucks. And now the Bruins have locked him up for another seven seasons, for lessthan he's currently making. I'm starting to think Savard doesn't understand the concept of money.

Where was this kind of negotiating skill when it came time to re-sign Milan Lucic(notes)?

4. Robyn Regehr(notes), Calgary Flames

A premium is often put on offensive production over defense, and for obvious reasons. Not allowing the other team to score just isn't as fun because a blocked shot or a big hit will never be as sexy as a power play goal. And maybe that's why Robyn Regehr, one of the meanest, toughest and best defensive defensemen in the league, started getting a little over $4 million for five years last summer.

Regehr, everyone's favorite Brazilian NHLer, makes less against the cap per year than 31 other defensemen (many of whom only have defense in their name as a technicality). And the fact that he hasn't been a minus player in the five seasons prior to this one despite his career high in points being just 26 tells you just how undervalued defense really is. This guy played in the Olympics!

How does he make less than Eric Brewer(notes)?

3. Ryan Getzlaf(notes) and Corey Perry(notes), Anaheim Ducks

You, the nice person reading this, are probably not a fan of the Anaheim Ducks. And therefore you probably loathe Getzlaf and Perry.

But if you are an Anaheim fan, then you know that for the price of just over 1.25 Eric Staals, your favorite team locked up two of the most underrated players in the league this summer as both signed five-year deals with a cap hit of $5.325 million each.

In return for their $10.65 million, the Ducks get two players around which they can build a franchise. Both do everything you could want a forward to do: agitate, control the boards, draw penalties, physically bully other teams and, of course, score. And score a lot. In the two seasons prior to their new contracts, Getzlaf and Perry combined for 110-189-299, and both had their names on the Stanley Cup as 21-year-olds.

That's worth a hell of a lot more than what they get paid.

2. Zach Parise(notes), New Jersey Devils

Before the 2007-08 season, Parise was rewarded by Lou Lamoriello for his strong rookie and sophomore campaigns in which he totaled 94 points (including 31-31-62 as a 22-year-old) with a four-year deal worth a modest $13 million. Decent money for a slightly-better-than-decent player.

His 31-31-62 season was followed with a 32-33-65 season, which isn't bad. But the big change was defensively. He went from scoring 62 and being a minus-3 to scoring 65 and being a plus-13. And then after that, Parise turned into a monster. The 2008-09 season saw Parise treat his opponents like Sherman treated Atlanta. A whopping 45 goals and 49 assists gave him 94 points and a plus-30(!).

This year, he has 15-15-30 in 24 games through Tuesday and he's already a plus-19.

And he's got another year on this deal after this one. That's not even fair.

1. Tim Thomas(notes), Boston Bruins

One of the last pieces of business Mike O'Connell performed as general manager of the Bruins before he was catapulted out of town like Rex Banner was to sign an aging, then-kinda-1b goalie Tim Thomas to a three-year deal. The deal was kind of pricey for a backup but not crazy or anything. The next year Thomas put up pretty bad numbers in 66 games, 3.03/.905, as the Bruins struggled under Dave Lewis and gave time to five different goalies. But after that, oh boy.

Despite a lackluster offense and a defense that would simply not show up some nights (I vividly remember being in the Garden to cover an 8-2 beating at the hands of the Maple Leafs four days after they gave up 10 to Washington), Thomas put up an incredibly respectable 2.44/.921 and got the Bruins into the playoffs pretty much by himself.

Last year, he helped the Bruins come within a game of the President's Trophy, secure the first seed in the East and had a goals-against of 2.10 and a save percentage of .933 and won the Vezina.

The cap hit for those three seasons: $1.1 million each. You might not find a bigger bargain in NHL history.

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