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Joel Auerbach/Getty Images David Clarkson #71 of the Toronto Maple Leafs

Hockey’s Worst Contracts

Ranking the NHL’s crummiest deals. (You know where this is headed, Vancouver fans. You too, Buffalo.)

Bad deals are inescapable in sports and pop culture. Endless, exorbitant, ridiculous contracts can destroy a team’s future, ensnare a rising young star, or cripple a major studio. Also, they’re hilarious. In honor of these horrible agreements, we present a look at some of the most egregious in their respective fields. Welcome to Worst Contracts Week.

Welcome to Grantland’s Worst Contracts Week — NHL Edition. I like that title. It rolls off the tongue a little nicer than my original proposal: “Good god, NHL GMs, when will you learn to stop throwing money at unpredictable goalies and terrible free agents, why are you all so stupid???”

For the most part, we’ll be running with the same approach that Jonah Keri used for baseball. But hockey’s salary landscape has a few unique quirks, so let’s lay out some ground rules.

• The NHL assigns a cap hit by averaging a player’s total salary (including bonuses) across the entire contract, and that value never changes during the life of the deal.1 That’s really the number we’re interested in here, even if the actual salary rises and falls over the course of the contract. I noted a few cases where the structure was especially creative, but we’re focusing on the cap hit, not actual dollars spent.

• The length of the contract matters, and in many cases is a bigger factor than the cap hit. Contracts that expire within the next year or two had to be really bad to even enter the discussion. Dany Heatley’s $45 million deal turned out to be a disaster for several teams over the years, but it expires at the end of this season, so it’s not really a bad deal today.

• It won’t surprise you to see that several of the controversial “cap circumvention” deals from years past show up below. Remember, the new cap recapture rule makes those contracts especially tough on teams that are stuck with them.

• Yes, the salary cap will keep rising. We all get that. That helps in some cases, especially if a player’s production is likely to stay flat or increase, but it isn’t a blanket excuse for giving out ridiculous long-term deals.

• We won’t penalize or reward teams based on whether they have any compliance buyouts left,2 though I did note a few cases where it’s pretty clear that one could be used. If the best defense of a contract is “Well, they can always just buy it out,” then it’s a bad contract.

• Unofficially retired players like Chris Pronger and Marc Savard who are on the long-term injured reserve list aren’t considered bad contracts, since their teams are getting cap relief.

• We’re worrying only about contracts that are currently on the books, not extensions that have been signed but have not yet kicked in. You’re off the hook for now, Corey Crawford and Henrik Lundqvist.

And remember, this is a snapshot of the league’s worst deals right now. For each contract below, “years” refers to how many seasons are left (including this current one), not how many were on the original deal.

Honorable Mentions

You may be expecting to see some of these guys on the list, but they didn’t make the cut. Here’s why.

Ryan Suter and/or Zach Parise, Minnesota Wild: Both their deals are obviously ludicrous. But hockey is increasingly becoming a sport where it’s worth paying big money for elite talent, even if you have to skimp everywhere else to do it. Are these guys elite? Suter seems to be. Parise … check back with me next year.

Shea Weber, Nashville Predators: He probably has the most ridiculous contract in the league, but if the Predators decided to trade him, their phone would be ringing off the hook.

Travis Zajac, New Jersey Devils: I really want to hate his eight-year contract. But Devils fans seem fine with the deal — even oddly happy with it. I still reserve the right to say “I told you so,” but for now, I’ll leave him alone.

Ondrej Pavelec, Winnipeg Jets: I’m not a big fan of his work, and $3.9 million is too much for what he brings to the table. But as far as goalie deals go, this one is practically reasonable.

Ryan Malone, Tampa Bay Lightning: Thankfully, just two years left.

Roman Josi, Nashville Predators: This was a weird deal, and it probably set the record for most years given to a player you’d never heard of, but you could defend it.

Brian Campbell, Florida Panthers: A few years ago it probably makes the list, but his deal expires in 2016, and Campbell’s actually been pretty darn good this year.

Tyler Bozak, Toronto Maple Leafs: I didn’t like the deal at the time and I still think Mikhail Grabovski is better, but Bozak’s been earning his money this year.

Tuomo Ruutu, Carolina Hurricanes: To be honest, I already felt like I was being too hard on the Hurricanes. Uh, spoiler alert.

Any Member of the Philadelphia Flyers: I know, I was as shocked as you are. But while the Flyers have lots of bad deals — Mark Streit, Luke Schenn, Scott Hartnell — none are bad enough to make the top 15. And by the way, despite an off year, I’m not convinced the upcoming Claude Giroux extension was a mistake.

The 15 Worst Contracts

15. Marian Hossa, Chicago Blackhawks: $5.275 million x 8 years


Hossa is a great player, and he’s a steal at a cap hit just north of $5 million. So how can his contract be considered bad? Simple: It goes on forever.

Well, not quite forever. Just until 2021, at which point, Hossa will be 42 years old. Hossa’s deal was one of the most egregious examples of the blatant cap circumvention deals that swept the league toward the end of the old collective bargaining agreement. It wasn’t even especially subtle — Hossa makes $7.9 million a season in real dollars until 2016, then sees his pay plummet to an eventual $1 million over the last four years of the contract. That’s some serious front-loading. If he retires in 2016, the Hawks will take a cap recapture hit of $3.6 million a season for five years.

The Blackhawks signed Hossa in 2009 and went on to win two Cups with him (and counting), so it’s hard to imagine they regret this deal. But it’s going to look bad within a few years and stay that way for a long time.3

14. Jonathan Quick, Los Angeles Kings: $5.8 million x 10 years


This one could come back to bite me, and soon. Within two weeks, Quick could be walking around with a gold medal around his neck and “consensus best goalie in the world” label slapped on his chest, and you’ll all hunt me down to point and laugh.

But that’s the thing about this deal — for it to make sense, Quick pretty much has to be the best goalie in the world. And during the 2012 Stanley Cup playoffs, that’s exactly what he was. For the rest of his career … not so much.

Since Quick became a starter in 2008, 27 goalies have played at least 200 games. Quick ranks right in the middle in terms of save percentage, sitting 15th. Being the 15th-best goalie in a league of 30 teams isn’t bad at all. But is it worth the third-biggest goalie contract in the league? Remember, NHL teams don’t exactly have a history of getting good value out of long-term goalie deals. Other goalies who’ve received deals for a decade or longer have included Rick DiPietro and another guy we’ll get to further down the list. Goaltending is just really, really hard to predict.

And it’s not like “L.A. Kings goalie” is exactly one of the toughest job descriptions around. The Kings are one of the best defensive teams in the league, and when Quick was hurt for almost two months earlier this season, they didn’t miss a beat — career backup Ben Scrivens and undrafted rookie Martin Jones put up excellent numbers.

It feels like the best possible outcome here for the Kings is that they get OK value. The worst-case scenario … well, we’ve already seen it.

13. Jordan Staal, Carolina Hurricanes: $6 million x 10 years

Carolina Hurricanes' Jordan Staal

AP Photo/Ross D. Franklin

Staal orchestrated a trade out of Pittsburgh during the 2012 offseason, largely because the former second overall pick was tired of being stuck behind Sidney Crosby and Evgeni Malkin on the depth chart. The Hurricanes acquired him, and then immediately signed him to a long-term extension worth first-line money that kicked in this season.

So far, Carolina hasn’t received anything near first-line production. Staal has put up just 58 points in 105 games for the Hurricanes, and it looks like he’ll fail to crack the 40-point mark this season. You don’t measure a player like Staal based purely on points — he’s an excellent two-way player — but for $60 million, you have to be hoping for a little more than Rich Peverley numbers.

At 25, Staal is one of the youngest players on this list, so there’s still time for this deal to work out. But so far it’s been a major overpay.

12. Tyler Myers, Buffalo Sabres: $5.5 million x 6 years


Well, at least you can see what the Sabres were thinking here. Myers won the Calder Trophy after scoring nearly 50 points as a rookie in 2010, and at 6-foot-8, you had to wonder if the Sabres had found themselves the next Zdeno Chara.

His sophomore year wasn’t quite as productive, but he still looked good, and during the 2011 offseason, the Sabres decided the time was right to get the 21-year-old locked up long-term on a seven-year extension that would kick in the following year. But Myers’s play continued to fall off in 2011-12, and by the lockout-shortened 2012-13 season, he managed just eight points while struggling to keep a spot in the lineup.

This year, Myers’s game has rebounded somewhat. He’s not worth his paycheck right now and might never be again, but he’s young enough that there’s at least some hope he can be a useful piece of the Sabres’ rebuild, instead of an albatross. If he can put together another solid season, he won’t be on next year’s list.

11. Nathan Horton, Columbus Blue Jackets: $5.3 million x 7 years


Horton’s a big power forward with a Cup ring. That’s good. He also managed to play more than 70 games in a season only once since 2007-08. That’s not so good.

Granted, one of those years included the 2012-13 work stoppage, when Horton played 43 out of 48 games, so we can give him credit for two healthy seasons out of six. But he missed almost half of 2011-12 with a concussion and the first 40 games of this year recovering from shoulder surgery. Committing seven years to a player who relies on a physical game but can’t seem to stay healthy seems like a significant risk.

There’s some logic to the idea that a franchise like the Blue Jackets might have to overpay to land free agents. I’m just not sure Horton’s the guy you want to roll the dice with.

10. Johan Franzen, Detroit Red Wings: $3.95 million x 7 years


When Franzen signed his 11-year extension in April 2009, he was just finishing up his first 30-goal season. While it was unusual to see a team commit so many years to a 29-year-old, his cap hit was more than reasonable for a guy who scored in that range.

He hasn’t hit that 30-goal mark again since then, but he came close over the first few years of his deal. He missed most of 2009-10 to injury, but scored 28 goals in 2010-11 and 29 in 2011-12. In the lockout year, he managed 14 in 41 games. That was a drop in his goals-per-game rate, but not a major one.

But this year, his scoring rate is down once again, and has dipped below .30 per game for the first time since 2007. He’s 34 years old and has battled injuries. It’s fair to say that while the Wings may have received good value for their money over the past few years, they’re solidly into the “declining returns” phase of the deal.

And that’s bad news, because there’s an awful lot of years left. Franzen is signed through 2020, at which point he’ll be 40 years old. It’s hard to see him making it anywhere near that far without being bought out.

9. Pekka Rinne, Nashville Predators: $7 million x 6 years


Rinne was coming off a 2011 Vezina nomination when the Predators gave him a seven-year, $49 million extension on his 29th birthday. He was nominated again in 2012, even though his numbers dropped slightly.

But by the time the extension kicked in last season, Rinne was merely average, finishing 23rd in save percentage among goalies with at least 20 games. This season was supposed to be a bounce-back year, but instead he’s missed most of it with a hip infection. You can’t blame a guy for suffering a fluke injury, but the Predators now find themselves on the hook for the league’s second-highest goalie cap hit4 through 2019, when Rinne will be 36.

Seriously, NHL teams, stop signing goalies to long-term deals that take them well into their thirties. I promise I’ll mention this only once more.

8. P.K. Subban, Montreal Canadiens: $2.875 million x 1 year


Wait, what?

Subban is the reigning Norris winner. He was selected for Team Canada. He’s only 24, and he’s already one of the most entertaining talents in the league. He is, to put it bluntly, awesome, and at less than $3 million a year, he’s an absolute steal.

So how can he possibly make this list? Because unlike everyone else we’ve mentioned, his contract is actually too small. Let me explain.

Heading into the 2012-13 season, Subban was a restricted free agent coming off a solid second NHL season. He wanted a long-term deal, but the Montreal front office didn’t want to make that sort of commitment. After a brief impasse,5 the Habs got their way. Subban signed an inexpensive two-year deal, after which Montreal would still hold his rights. The Canadiens won, and won big.

Or at least that’s what we all thought. (And by “we all,” I mean me.) There was a risk — by passing on the chance to lock down Subban, the Habs risked paying even more if he broke out before his next extension.

You know what happened next. Subban was named the league’s best defenseman that year, and — so far this season — has largely picked up where he left off. And with his contract up this summer, he’s about to get paid. Montreal probably could have signed him for something in the range of $5 million. Now it may end up paying him nearly twice that.

Nobody predicted that Subban would win the Norris, and obviously the Canadiens have to be thrilled he did. But they probably cost themselves a ton of money by “winning” that contract showdown in 2012.

7. Alexei Yashin, New York Islanders: $2.2 million x 2 years


Wait, does he qualify? I know he hasn’t played an NHL game in almost seven years, but his buyout is still on the Islanders’ books through next season. Can I get a ruling here?

OK, fine, active players only. You’re off the hook, Alexei.

7. Alexander Semin, Carolina Hurricanes: $7 million x 5 years


Early in his career, Semin was one of the league’s most exciting and productive players. He had topped 70 points three times with the Capitals by the age of 25, peaking with a 40-goal, 84-point year in 2009-10.6 But after two consecutive 54-point years, Washington decided to let him test free agency in 2012.

He didn’t find anyone willing to open the vault on a long-term contract, so he signed a one-year “show me” deal with Carolina. It was a smart deal for both sides. He was a point-per-game player in 2012-13, and that was good enough for the Hurricanes, who gave him $35 million.

The early returns haven’t been encouraging, as Semin is producing points at his lowest rate since he was a teenage rookie in 2003-04. That’s led to questions about his motivation that, let’s be honest, we wouldn’t hear as frequently if he had a different passport. But a bigger concern is that he turns 30 in a few weeks, so his best years should be well behind him.

Only 11 other forwards are on the books for a $7 million cap hit through at least 2018, and their names are Ovechkin, Malkin, Crosby, Perry, Giroux, Getzlaf, Kessel, Nash, Parise, and the Sedins. Right now, Semin doesn’t look like he’s even in that ballpark.

6. Brad Richards, New York Rangers: $6.67 million x 7 years


The contract Richards signed as an unrestricted free agent in 2011 was a classic front-loaded cap circumvention deal. He makes $57 million of this $60 million total in the contract’s first six years, then just $3 million over the final three. Clearly, the Rangers were hoping to get a few years of good value, a few years of not-so-great value, and then see him retire by 2017.

Even that might not have been a good bet, since Richards was already 31 when he signed. But he was coming off two consecutive years of posting a point-per-game rate above 1.0 and was the only real star available in the free-agent class of 2011, so the Rangers paid up. Within two years, Richards was getting scratched in the playoffs.

Given how much attention that benching got, you might be surprised to look through Richards’s numbers in New York. He hasn’t been bad, posting better than .75 points per game to rank in the top 60. Those are borderline first-line numbers. He’s far from washed up.

But again, it’s all about length. Richards is about to turn 34, and he’s signed through 2020. It’s all but a sure thing the Rangers will use a compliance buyout on him during the offseason.

5. Stephen Weiss, Detroit Red Wings: $4.9 million x 5 years


For years, Weiss was one of those “fly under the radar” guys, toiling away for the Florida Panthers. You’d kind of forget he existed, and then every so often, you’d see his stat line and think Hmm, not bad at all.

He was awful in 2012-13, scoring just four points in 17 games. But he was hurt most of the year and had a solid track record. When he made it to free agency in a talent-thin market, you knew someone would pay up. What was he going to do, have another injury-plagued season in which he scored four points?

He wound up getting $24.5 million from the Red Wings, and they’ve been rewarded with … another injury-plagued season in which he’s scored four points. That’s all he’s managed so far, while struggling with a groin injury that has limited him to 26 games.

Lots of people loved the Weiss signing in the summer, when he seemed like one last piece of the puzzle for a Wings team expected to contend for the Cup. Now that they’re struggling just to make the playoffs, a five-year commitment to a banged-up center on the wrong side of 30 seems like a major misfire.

4. Ryane Clowe, New Jersey Devils: $4.85 million x 5 years


On paper, Clowe shouldn’t have been an especially sought-after free agent last summer. He was coming off a year in which he’d gone goalless for the San Jose Sharks before being dealt to the Rangers at the trade deadline, where he managed to up his season total to three. He’d been hurt in the playoffs, was two years removed from his best season, and was 30 years old with a long history of injuries.

But Clowe’s the sort of big body who can bang and crash and (occasionally) score, and NHL GMs seem to love him. So the Devils stepped up and gave him nearly $25 million.

Devils fans didn’t especially love the deal at the time, and they loved it even less when he missed almost the entire first half of the season with another concussion. It’s one thing for a player to suffer an unpredictable injury that torpedoes his value. That happens, and there’s not all that much you can do about it. But Clowe’s health was a known risk, and the Devils got burned. When he did return to the lineup, he didn’t produce much, and is sitting on just three goals in 27 games.

Would now be a good time to point out how many of these deals came via unrestricted free agency? The next time somebody complains that their team spent the first day of free agency on the sideline, send them a link to this piece and tell them that their GM deserves a raise.

3. Roberto Luongo, Vancouver Canucks: $5.33 million x 9 years


Given how often Luongo’s deal is criticized — “My contract sucks,” Luongo himself once said — you may have been expecting to see it holding down the top spot on this list.

But while the length of Luongo’s deal is ridiculous, his current cap hit actually offers the Canucks some solid value. He’s one of the better goalies in the league, and he has been just about the only bright spot in Vancouver all season. And right now, he’s not even in the top 10 for cap hits among goalies. Other than the length, this contract looks pretty good.

But saying that Luongo’s deal is OK except for the length is like a Leafs fan saying Game 7 of last year’s first-round playoff series against Boston went fine except for the last 12 minutes. Luongo will be 43 by the time his deal expires, and he plays a position that typically sees a steep performance decline around a player’s mid- to late thirties.

The Canucks front-loaded Luongo’s deal, obviously expecting him to retire early and wipe off the remaining cap hit. That was how the rule worked at the time, when the contract was signed (and, it is worth remembering, approved by the league). But the NHL changed the rules, and Luongo’s deal will now invoke a cap penalty when he retires — some of which would stay with Vancouver even if he’s with another team. You can make a strong case that it’s not fair to the Canucks, but it’s reality.

The Canucks tried to get clever with CBA loopholes when they signed Luongo’s deal, and they got burned. It’s already cost them Cory Schneider. They’d better hope they luck out and Luongo can buck the historical aging trends, because otherwise it’s going to get a whole lot worse.

2. Ville Leino, Buffalo Sabres: $4.5 million x 4 years


Leino was one of the beneficiaries of the Sabres’ bizarre 2011 spending spree under new owner Terry Pegula.7 He’d just finished his third NHL season and posted 53 points (42 more than his previous career high) when Buffalo decided to hand him $27 million.

They’ve yet to see any value for their money. Leino managed just 25 points in his first year in Buffalo and played just eight games in the second. This year, he’s played 38 games and has yet to score a goal. Several times during the season, he’s been a healthy scratch.

The only good news for the Sabres is that, with four years left, this is one of the shorter deals on the list. That should at least make the inevitable buyout easier to swallow.

1. David Clarkson, Toronto Maple Leafs: $5.25 million x 7 years


Lots of bad contracts seem like a good idea at the time, only to turn sour as the years go by. Clarkson’s deal, signed on the first day of free agency last summer, was almost universally panned from the very moment it was announced. I hated it. Sports Illustrated said “the money is unnerving, but the term is absolutely frightening.” Yahoo said it “has regret written all over it.” Sporting News used the deal to call the Maple Leafs free agency’s “biggest losers — by a lot.”

That was seven months ago. Since then, things have gotten much, much worse.

Taking a $5.25 million cap hit on a player who had just one 40-point season in his career always seemed like a stretch. To do it for a max-length seven-year deal on a power forward who was already almost 30 was madness. It was a virtual certainty that Clarkson’s best years were already behind him, and the odds were good that a steep drop in production was looming. Oh, and the deal was even structured in a way that would make it especially painful to buy out.

All of which leads to the question: What the hell could the Maple Leafs have been thinking? Maybe they were still traumatized by their season-ending collapse against the Bruins, and felt like Clarkson’s intangibles were somehow worth big money. Maybe coach Randy Carlyle’s fighting fetish ruled the day. Or maybe they just figured that when all the fancy stats pointed in one direction, they’d go and do the opposite, since that strategy tends to work out OK for them.

In any case, even GM Dave Nonis didn’t try to defend the length of the deal. “I’m not worried about six or seven [years] right now,” Nonis said at the time. “I’m worried about one. And in Year 1, I know we’re going to have a very good player.”

That’s the sort of quote that should horrify any fan of the team that offers it, because Nonis was essentially acknowledging that the deal would be a disaster eventually.8 But the Leafs were willing to accept future pain to get a short-term boost.

But three-quarters into that Year 1, Clarkson is having the worst season of his career. He has just four goals and 10 points. He’s missed a third of the season to injuries and suspensions. When he does play, he shoots far less, and his shooting percentage has cratered. He rarely gets power-play time. He was supposed to be the prototypical Randy Carlyle player, but Carlyle can’t figure out how to use him.

As a Leafs fan, the whole thing has been painful to watch. I’ve always felt like we overuse the whole “he’s trying to do too much” school of sports narrative, but Clarkson fits it perfectly. The poor guy clearly wants so badly to be one of those beloved heart-and-soul Maple Leafs, in the Wendel Clark mold.9 He got himself suspended for jumping into a preseason brawl to help a teammate who didn’t actually need any help. He keeps trying to come back from injuries too quickly, then doesn’t play well. He anointed himself the team’s water bottle guardian. And through it all, whenever he’s on the ice, he always has this wild-eyed look of desperation, as if his internal monologue is constantly screaming at him to do something, anything.

There’s still hope. Even the biggest Maple Leafs homers have come to hate his contract, but most haven’t yet turned on him as a player. He seems like a good guy who was genuinely excited to play for his hometown team. Give him one good playoff series, and the short-term redemption story practically writes itself.

But at this point that’s the best-case scenario for Year 1, and even if it happens, this contract will still have six long years to go. You can still like the player, but there’s just no defending the deal. In a league full of awful contracts, Clarkson’s is the worst of them all, and it’s not even close.

Previously in this series: Baseball’s worst contracts

Filed Under: NHL, Hockey, David Clarkson, Ville Leino, Roberto Luongo, Ryane Clowe, Stephen Weiss, Brad Richards, Alexander Semin, Alexei Yashin, P.K. Subban, Pekka Rinne, Johan Franzen, Nathan Horton, Tyler Myers, Jordan Staal, Jonathan Quick, Marian Hossa, Worst Contracts Week

Sean McIndoe ’s work can be found at Down Goes Brown. When he's not writing, he makes hockey jokes on Twitter at @downgoesbrown.

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