Risks and rewards of long contracts

How long will Sidney Crosby's next contract be ... and will it be in Pittsburgh? Bruce Bennett/Getty Images

It's hard to find too many long-term contracts that have worked out. Those deals, often structured to circumvent the salary cap, typically range from ill-advised to disastrous. Rick DiPietro never came close to making his 15-year deal pan out. Chris Pronger may never play again, just a couple of years after signing a seven-year deal. Jeff Carter was traded twice in the first year of his 11-year contract. Alex Ovechkin's $9.5 million average salary extends through the 2020-21 season, a healthy payday for a player whose production is already declining.

But while there's some building evidence that these contracts aren't a great idea, it might not matter this summer. The willingness of teams to continue to assume that risk will shape the biggest personnel moves of the offseason.

First, there's the Roberto Luongo situation. He's all but certain to get traded, which means somebody will be acquiring a 33-year-old goalie with 10 more years left on his contract. Second, there's the Ryan Suter and Zach Parise sweepstakes. If they hit the market, they aren't doing it to take a short-term deal. They are far and away the two best potential free agents, and they will get paid like it. And third, there's Sidney Crosby. The Penguins and Crosby can start talking contract extension July 1 in a negotiation that will be the most crucial in franchise history.

And all these decisions will be made against the backdrop of an expiring CBA, where the future of long-term contracts is heavily in doubt, as are the ways in which teams can move them.

Penguins GM Ray Shero said his goal this summer is to re-sign both Crosby and Jordan Staal. Crosby admitted that the expiring CBA might delay the talks as both sides try to get a feel for what the future holds. But it's not just the CBA that complicates things; it's Crosby's health. There's no doubt that when he's healthy, he's the best player in the world. He put up 37 points in 22 regular-season games. And during a postseason that won't go down as one of his best, he still put up eight points in six games.

"We'll be talking to the Penguins in the near future. He's a huge asset," said Crosby's agent, Pat Brisson, when we chatted this week. "Sidney Crosby is one of the biggest, if not the biggest, assets in hockey. He's still a young man and he's very healthy."

Brisson said this offseason is a crucial one for Crosby. He passed on an opportunity to play in the world championships because he wants to refocus his training and finally return to the kind of summer program that made him the best player in the world. His offseason work ethic is the reason Crosby always returned to training camp better than he left at the end of the season. This summer, he'll have that opportunity again.

"Everything is mapped out," Brisson said. "The summer for a hockey player is everything."

Long-term deals are already risky, but with Crosby there are even more considerations. He showed his durability during a physical playoff series against the Flyers but his concussion history can't be ignored. If he gets a long-term contract, it's reasonable to wonder just how many years he'll be able to complete. One unfortunate moment could change everything, and it's something Shero will have to weigh when he sits down with Brisson.

But what's the alternative? Let the best player in the world hit free agency in 2013? That's the bigger risk.

"I have absolutely no concern about the position Sidney is in regarding his contract," Brisson said. "No concern."

One GM suggested that there's considerably less risk in giving a long-term contract to your own core player like Crosby rather than acquiring one through free agency or trade. That's the challenge suitors for Suter and Parise will face this summer.

The line was long to sign Brad Richards last summer, and he eventually got a nine-year deal at the age of 31. It looks good now with the Rangers in the second round and Richards a big part of the reason. That will only encourage those courting Suter and Parise.

If Richards got nine years in his early 30s, what kind of deal will two players entering their prime receive? Parise and Suter are just 27 years old and will no doubt have their choice among contract offers that will offer security for at least the next decade. At least.

"We've made some decision in the past on [Henrik] Zetterberg and [Johan] Franzen that are long-term deals," said Red Wings GM Ken Holland, who is expected to be aggressive in free agency this summer. "I don't know how many of those you can have on one team."

And that may be the biggest roadblock for teams pursuing Suter and Parise. If you already have a couple of these long-term deals on the books, is it a great idea to lock in another one? Should ownership even allow it?

The answer is yes, if you want to lure elite talent to your franchise.

"We've got money; what we don't have is players," one NHL source said. "If I'm a GM, I'm using every opportunity to acquire significant assets any way I can."

Perhaps that's the reason interest in Luongo might be more significant than originally thought. His contract initially looked impossible to trade, but when you start penciling him into different lineups, he's still a difference-maker. Put him in Toronto this year and the Maple Leafs make the playoffs. Same with Tampa. The Blackhawks might still be playing right now if Luongo was their goalie.

But trading for one of those long-term contracts is an entirely different debate. Signing your own core player is the easiest path. You know what you're getting. Signing a free agent isn't bad either because you know he's eager to join your team. Trading for a player on a long-term contract doesn't come with any guarantee, like Columbus discovered last season.

"When you trade for one, it's a different animal than signing because you don't really know the player," said Blue Jackets GM Scott Howson, who acquired Jeff Carter and traded him eight months later. "You weigh the benefits, the pros and cons. You decide 'This is something we're willing to try.' Most of these players are very, very talented players. They're good players in the league."

Columbus could use a goalie of Luongo's caliber and could catapult into playoff contention with him on its team next season. He's an option they'll at least consider internally. But the painful lessons of the past are a reminder that just acquiring talent isn't always enough. It has to be a fit.

Luongo will be providing a list of teams he'd like to join and if the Blue Jackets aren't on it, it's probably not in their best interest to try and change his mind. Nobody should. There has to be a willingness from both sides to make it work.

"Certainly we would be even more hesitant now," Howson said, not specifically about Luongo but of acquiring any player signed long-term. "Right now, we just don't know the landscape."

That's the wild card in all of this. Every general manager is repeating the programmed line that this summer is business as usual. It's not. With the CBA expiring in September, there's going to be a new set of rules. The NHL would love to close the loophole that allows long-term contracts to significantly lower salary-cap hits. It might be in Pittsburgh's best interest to get Crosby signed long-term to a cap-friendly deal while it's still allowed.

Despite talk that amnesty won't be an option in the new CBA, there are still people around the league who believe teams will have more flexibility to get out of bad long-term deals once a new CBA is agreed upon.

"I believe there will be a mechanism by which we'll be able to fix our problems on our teams, to keep those assets we want and get rid of the assets we don't," an NHL source said. "It would be silly to do it any other way."

There's growing belief that the next CBA will allow teams to eat a portion of a salary during a trade, something that isn't allowed now. Luongo's trade value would be significantly higher if the Canucks were allowed to pay half his salary moving forward. Big-market teams like that option because it gives them the flexibility to get out of bad deals. Small-market teams like it because they can add a player they otherwise wouldn't be able to afford at a discount.

"From the league side, before that was a nonstarter. Now, I think it's going to be integrated," an NHL source said. "It makes sense. It saves money and it serves as an alternative revenue sharing."

It's another factor to weigh in what could be one of the most fascinating offseasons in a long time.