Thanks to Roberto Luongo, Vincent Lecavalier, Ilya Bryzgalov, and Rick DiPietro, the past week of NHL transactions will probably be remembered as the Revenge of the Long-Term Contracts. With Luongo trapped in Vancouver and the other three players receiving buyouts that total almost $80 million, teams that tried to beat the system with extended deals are starting to feel some serious pain.

After years of teams signing players to ridiculously long-term deals, often front-loading them to exploit a salary-cap loophole, the NHL moved to put a stop to the practice in the last CBA by limiting contracts to a maximum of eight years. But the contracts signed under the old CBA still remain, and many of them don’t look good.

So I thought it would be a good idea to go through the full list of contracts longer than eight years that were signed during the salary-cap era and do a player-by-player breakdown of all [checks CapGeek] 21 of them.

Wait, 21? I’ve got to be honest, that’s way more than I thought there would be. What the hell, NHL owners? This is going to take a while.

[Strongly considers introducing an arbitrary cutoff like “12 years” and going to lunch early.]

[Ah, screw it, let’s do this.]

Here’s a look at each of those 21 contracts of nine years or longer, as we try to answer one question: In hindsight, did any of them actually turn out to be a good idea?



Ilya Kovalchuk, New Jersey Devils

How much: 15 years, $100,000,000

How long: Expires in 2025, at age 42

Cap circumvention? Oh yeah — so much so that the league rejected the first version of the contract, which was a ridiculous 17 years. The league also fined the Devils $3 million and stripped them of a first-round pick. The updated contract was more realistic, barely, and was approved.

What were they thinking? Kovalchuk was an unrestricted free agent, still in his prime, and was considered one of the best players in the league (he was coming off six consecutive 40-goal seasons). If any player deserved this kind of deal, it was Kovalchuk.

Is it terrible? Spoiler alert: No player deserves this type of deal, and this one will look like a train wreck for New Jersey long before it’s done. As just one sample scenario, if Kovalchuk retires in 2020 when the $1 million years kick in, the Devils will take a $4.6 million recapture charge for five seasons.

Shea Weber, Nashville Predators

How much: 14 years, $110,000,000

How long: Expires in 2026 at age 40

Cap circumvention? Yes. Weber makes $56 million in the first four years (of which an astounding $52 million comes via signing bonus) and only $3 million over the final three. But there’s an asterisk on this one, which we’ll get to in the next section.

What were they thinking? Weber’s massive contract with the Predators wasn’t actually signed with the Predators — he made the deal with the Flyers as a restricted free agent in 2012. The super-expensive and front-loaded deal was designed to be impossible for the cash-strapped Predators to match. They matched it anyway.

Is it terrible? Probably. Today, Weber is one of the best defensemen in the league. It’s not unprecedented for stud blueliners to play at a high level well into their 30s — Ray Bourque, Scott Stevens, and Chris Chelios all played until they were 40 or beyond — and maybe Weber will too. But if he starts to fade, this deal could be crippling for the small-market Predators franchise.

Ryan Suter and Zach Parise, Minnesota Wild

How much: Identical contracts of 13 years, $98,000,000

How long: Both players’ deals expire in 2025 at age 40

Cap circumvention? Yep and yep.

What were they thinking? Parise and Suter were the two best free agents of the 2012 class and had expressed a desire to play together. Also, Wild owner Craig Leipold likes to be “bodacious,” which is a fantastic word that the rest of us don’t use often enough.

Are they terrible? Probably, though Suter’s near-Norris season was a good start, and there’s a chance he could be one of those defensemen who play well for a long time (see Shea Weber). Of the two, Parise is more likely to be seen as a mistake. His prorated 2013 numbers were right around his career average, which is to say they were solid but a notch below superstar levels. Given that forwards tend to peak earlier than defensemen, it may not be long before his deal starts looking ugly.

Johan Franzen, Detroit Red Wings

How much: 11 years, $43,500,000

How long: Expires in 2020 at age 40

Cap circumvention? Indeed.

What were they thinking? Franzen was 29 years old and coming off his only career 30-goal season and a pair of strong playoff runs when he signed this extension in 2009.

Is it terrible? At least it’s cheap. This is the only deal on the list that carries a cap hit of less than $4 million. And Franzen’s game relies on size, a heavy shot, and driving the crease to bang in dirty goals, all of which are characteristics that don’t fade as rapidly as speed and quickness. If he doesn’t wear down from all the punishment he absorbs in front of the net, this one may actually turn out OK. But that’s not a small “if.”

Duncan Keith, Chicago Blackhawks

How much: 13 years, $72,000,000

How long: Expires in 2023 at age 39

Cap circumvention? Aye.

What were they thinking? Keith’s really good. He won the Norris as the league’s best defenseman in 2010.

Is it terrible? Consider this: Keith’s points per game has been remarkably consistent, hovering between 0.54 and 0.57 in four of the past five years. The one exception was a 0.84 in 2009-10, which, coincidentally, was the season before he signed his extension. That season is starting to look like a major outlier.

Of course, Keith’s game is more than just offense. And it’s also worth mentioning that the Blackhawks just won their second Cup in four years, so we can’t discount the possibility that they may know what they’re doing.

Henrik Zetterberg, Detroit Red Wings

How much: 12 years, $73,000,000

How long: Expires in 2021 at age 40

Cap circumvention? I’m running out of synonyms for “yes.”

What were they thinking? Zetterberg was coming off a 92-point season in which he was nominated for the Selke and won the Conn Smythe Trophy as playoff MVP, and was months away from unrestricted free agency when the Red Wings locked him up for the rest of his career.

Is it terrible? He hasn’t topped 80 points or made an All-Star team since signing the deal. But it’s the Red Wings, and hockey writers are never supposed to criticize any move they make, so let’s just move on.

Marian Hossa, Chicago Blackhawks

How much: 12 years, $63,300,000

How long: Expires in 2021 at age 40

Cap circumvention? Indubitably.

What were they thinking? Heading into the 2009 offseason, Hossa was an unrestricted free agent and wanted a long-term deal, so some team was going to have to pay up. The Blackhawks thought they were one player away from winning a Stanley Cup, so they paid.

Is it terrible? The Blackhawks turned out to be right about that Stanley Cup thing, so there’s that. But this deal looks pretty onerous right now [flips homemade “consecutive posts using the word ‘onerous’” sign to “2”], so much so that Hossa was the subject of some buyout talk this year. Chicago isn’t going to use that option now, but it may have no choice next offseason, if only to avoid a heavy cap benefit recapture penalty . [Editor’s note: Update!]

Vincent Lecavalier, Tampa Bay Lightning

How much: 11 years, $85,000,000

How long: Would have expired in 2020 at age 40

Cap circumvention? Yes. (I’m back to just saying “yes,” by the way.)

What were they thinking? Lecavalier was a former first overall pick who already had a Cup ring, had won a Rocket Richard, and was coming off a 92-point season when he signed this contract in 2009. And he was still just 28 years old. What could possibly go wrong?

Was it terrible? Oh, right, forwards usually peak in their mid-20s. I guess that would make giving them a massive extension right after that a potentially bad idea. And in Lecavalier’s case, it was — he immediately dropped from the “superstar” echelon to “good but not great.” Five years later, he’s still a useful player, but the contract was an albatross. The Lightning bought him out last week, spending an astounding $32.67 million to be rid of him. (Lecavalier signed a five-year deal with the Flyers on Tuesday.)

Alexander Ovechkin, Washington Capitals

How much: 13 years, $124,000,000

How long: Expires in 2021 at age 35

Cap circumvention? No, actually. Unlike virtually every other long-term deal that was signed in the years before the NHL signaled its annoyance with circumvention, this one isn’t front-loaded at all; in fact, Ovechkin gets a slight raise in the contract’s second half. This is because Capitals owner Ted Leonsis has too much integrity to try to cheat the system and/or wasn’t smart enough to figure out the same loophole everyone else found.

What were they thinking? Alexander Ovechkin is freaking awesome.

Is it terrible? The jury’s still out. On the one hand, the deal was signed five years ago and still features the league’s highest cap by more than $800,000 (though Evgeni Malkin’s new deal will come close when it kicks in for 2014). That suggests the Capitals failed to get any sort of discount for their long-term commitment, and may have misread the future market for superstar players entirely. Also, the explanation for the deal that they offered at the time didn’t really hold up to scrutiny.

On the other hand, Ovechkin just won his third MVP and will be young enough when this deal expires that it may not be the last one he signs. When Ovechkin’s play dipped over the last few years and into this season, this contract started to look like a disaster. These days, it’s veered firmly back into “maybe not so bad” territory.

Rick DiPietro, New York Islanders

How much: 15 years, $67,500,000

How long: Would have expired in 2021 at age 39

Cap circumvention? Nope. DiPietro’s salary was set to stay at a steady $4.5 million every season of the deal.

What were they thinking? I’ll pause here so you can all make your “It’s the Islanders, who says they were thinking at all?” jokes. But the reality is that the Islanders thought they were being innovative. DiPietro had been the first overall pick of the 2000 draft, and had a decent first year as a starter in 2003-04. His 2005-06 season wasn’t great, but he was 24 and entering his prime. The Islanders figured that even if he only ended up peaking at above average, $4.5 million would turn out to be a bargain.

Was it terrible? Indeed it was. The NHL’s original mega-deal turned out to be its original cautionary tale. DiPietro never lived up to the hype, was always hurt, and was eventually sent to the minors. On Tuesday, the Islanders placed him on waivers for the purpose of giving him a $24 million buyout.

Mike Richards, L.A. Kings

How much: 12 years, $69,000,000

How long: Expires in 2020 at age 35

Cap circumvention? Kind of, though this one isn’t really front-loaded. Is “middle-loaded” a word? I think we just made it a word.

What were they thinking? This was a deal he signed with the Flyers, so they were thinking “Let’s give this guy a crazy long contract and then have him play for us for a few more months.”

Is it terrible? It was definitely strange. When the Flyers gave him this deal, Richards was 22 years old and had played only two full seasons, never cracking 40 points. But he was 28 games into the 2007-08 season and was leading the team in scoring, so the Flyers were buying high.

The contract is the Kings’ problem now, thanks to a stunning 2011 trade. Richards hasn’t developed into an offensive star (he peaked at 80 points in 2008-09 and had just 44 in his first year in L.A.), but he’s considered one of the game’s best leaders and the Kings did win a Cup with him, so maybe it’s not completely terrible. But it’s probably a little bit terrible.

Jeff Carter, L.A. Kings

How much: 11 years, $58,000,000

How long: Expires in 2022 at age 37

Cap circumvention? Yes.

What were they thinking? This was basically the bookend to Richards’s deal, as the Flyers locked in the two players who would be the core of their teams for the rest of their careers. Fun fact: This is one of four mega-long-term contracts on this list that the Flyers signed with players who do not currently play for the Flyers. And we didn’t even get to talk about Chris Pronger or Danny Briere!

Is it terrible? Carter’s career season in 2008-09 remains the only one in which he’s cracked 40 goals, though he was scoring at a 44-goal full-season pace this year. His $5.2 million cap hit is a bargain by today’s standards, but likely won’t stay that way as he slows down through his 30s. Still, the Kings won the Cup with him, so scoreboard, I guess.

Sidney Crosby, Pittsburgh Penguins

How much: 12 years, $104,400,000

How long: Expires in 2025 at age 37

Cap circumvention? Yes, though they at least tried to be subtle. The final years only dip to $3 million per season, instead of down to $1 million like in other deals.

What were they thinking? You saw the part about it being Sidney Crosby, right? If the Penguins hadn’t signed him to an extension, he would have been a free agent this summer, when teams would have lined up to offer him checks with the words “all of the money” written on them.

Is it terrible? Assuming he stays healthy, this deal looks pretty darn good if he can maintain his current production. Careful readers will note that positive assessment was surrounded by two pretty huge qualifiers. As we all know, Crosby hasn’t been healthy very often over the past few years. And while it’s hard to imagine his production falling off sharply, it’s always hard to imagine that happening to a superstar until it does.

The bottom line is that any deal of this size carries significant risk. But if you’re going to take that risk, Crosby seems like as good a guy as any to take it on.

Roberto Luongo, Vancouver Canucks

How much: 12 years, $64,000,000

How long: Expires in 2022 at age 43 and oh god that can’t be right can it?

Cap circumvention? Put it this way: When the NHL creates a new cap benefit recapture rule to punish circumvention deals and everyone names it after you, your deal is cap circumvention.

What were they thinking? Luongo was considered one of the best goalies in the league when the Canucks extended him in 2009, but let’s face it — they were thinking that they’d beaten the salary cap because he’d retire well before this contract ended.

Is it terrible? It sucks. That’s not my opinion, it’s Roberto Luongo’s. And he’s right — this contract made it virtually impossible for the Canucks to trade him, meaning the poor guy has been stuck in the NHL purgatory for the last year (if being paid millions of dollars to play hockey once a week can be considered purgatory, which I think it can). Now he’s the starter again, and it’s just awkward for everyone.

Nicklas Backstrom, Washington Capitals

How much: 10 years, $67,000,000

How long: Expires in 2020 at age 33

Cap circumvention? No — like Ovechkin’s deal, it’s actually slightly back-loaded.

What were they thinking? Backstrom had racked up a 101-point season (good for fourth in the league) and was theoretically just entering his prime when he signed this deal in 2010.

Is it terrible? The jury’s still out. Backstrom hasn’t come close to his 2009-10 numbers, but he’s been close to a point-per-game player in the three years since. And despite the contract’s length, he’ll still be relatively young when it’s done. So while the Capitals may have overpaid, at least they overpaid for what should be most of a player’s prime.

Jordan Staal, Carolina Hurricanes

How much: 10 years, $60,000,000

How long: Expires in 2023 at age 34

Cap circumvention? Nope. It’s an even $6 million per year, every year.

What were they thinking? The Hurricanes had just acquired Staal from the Penguins, where he’d rejected a similar deal. He had never put up big numbers in Pittsburgh, but was a solid two-way player who many figured would score more once he wasn’t playing third fiddle to Crosby and Malkin.

Is it terrible? It’s early, but so far the results haven’t been great. Staal’s first season in Carolina was underwhelming (just 31 points in 48 games, to go with an ugly -18 rating). But he’s still just 24, and the extension doesn’t even kick in until next season, so there’s plenty of time left to judge.

Jonathan Quick, L.A. Kings

How much: 10 years, $58,000,000

How long: Expires in 2023 at age 37

Cap circumvention? A little bit toward the end.

What were they thinking? Quick had just single-handedly won the Kings a Stanley Cup. The end.

Is it terrible? It sure looked that way when Quick and his surgically repaired back had a below-average regular season in 2013. But another strong playoff run eased some of those doubts. One caveat: As the rest of this list demonstrates, long-term contracts to goaltenders have historically ended up in disaster.

Christian Ehrhoff, Buffalo Sabres

How much: 10 years, $40,000,000

How long: Expires in 2021 at age 38

Cap circumvention? Yes, including a $10 million first year that hilariously made Ehrhoff the second-highest paid player in the league that season.

What were they thinking? New owner Terry Pegula wanted to spend money. And hey, this deal couldn’t be any worse than the one they gave Ville Leino, right?

Is it terrible? The $4 million cap hit is actually pretty reasonable for a player like Ehrhoff, and could even end up looking like a bargain as the cap rises. Still, at 10 years and with a no-movement clause tacked on, the risk is substantial.

Brad Richards, New York Rangers

How much: Nine years, $60,000,000

How long: Expires in 2020 at age 40

Cap circumvention? Super-duper cap circumvention!

What were they thinking? Richards was the only star player available during the 2011 free-agency period. Glen Sather is Glen Sather.

Is it terrible? First things first: Right up until his playoff benching, Richards was actually reasonably productive during the first two years of this deal. But yes, this contract is terrible, because it goes on for seven more years and Richards is already clearly declining. With heavy recapture penalties looming, the Rangers will hope for one more year of him scoring 60ish points and then almost certainly use a compliance buyout on him next summer.

Ilya Bryzgalov, Philadelphia Flyers

How much: Nine years, $51,000,000

How long: Would have expired in 2020 at age 40

Cap circumvention? Of course.

What were they thinking? “We’re the Flyers and this is a decision involving goaltending so WHEEEE!”

Was it terrible? It may be the worst of all the deals on this list, and that’s saying something. Not only did the Flyers spend a ton of money on two years of disappointing goaltending, but they had to trade Richards and Carter to make room to do it. Oh, and the backup they traded away last year just won the Vezina. And now their starting goalie is Steve Mason. Yes, that Steve Mason.

Let’s all go back and read that last paragraph with “Yakety Sax” playing in the background.