The Penguins face such a situation now. With franchise centerpiece Sidney Crosby about to enter the final year of his current deal, the club is already working on a new agreement to keep Crosby in Pittsburgh for a long time. Reports over the weekend, most notably from Elliotte Friedman on Hockey Night in Canada on Saturday, proposed that a 10-year extension worth $90 million might be the terms it will take to get it done.
While Crosby cannot sign an extension until July 1, his representatives and the team can work on putting the parameters in place for such a deal. There's no question about the desire to keep arguably the best player in the league, but it's not quite so simple.
Crosby is the best player in the game when he's on the ice. But over the past two seasons, he hasn't been on the ice nearly as much as he, the Penguins, the rest of the NHL or hockey fans around the world would have liked.
A series of concussions forced Crosby to miss the final 41 games of the 2010-11 season and the playoffs that spring, plus the first 20 games of the 2011-12 season. After a brief return that lasted just eight games, as another concussion sidelined him for another 40 games.
He's been as effective as ever when he's played, collecting 37 points in the 22 games he did play last year and eight more in six games in the playoffs. But the risk of another concussion keeping him out for an extended stretch again or even ending his career is a major factor in making such a huge financial commitment to Crosby. That's especially true since the risk will almost definitely be the Penguins' burden alone as it's highly unlikely they will be able to get the contract insured due to Crosby's concussion history.
That's a significant risk, but still one that must be taken. It's certainly better than not signing Crosby and risking that he stays healthy after signing elsewhere and leads another team to a series of Cups. Friedman, in his weekly "30 Thoughts" column, spoke with five NHL executives on the issue, and each one said they would sign off on such a deal even without insurance.
"You know, it's a risk, but it's a risk you take," one GM told Friedman. A second GM noted, "If you don't do it, someone else is going to."
A third GM laid out the worst-case scenarios of passing on such a deal out of fear over the injury concerns: "If you sign him to this deal and he gets hurt in two years, you're going to look stupid. But if you don't, he plays the next 10 years like he can and goes down as one of the best ever, you're going to look even more stupid."
The injury risk isn't the only concern for the Penguins. There's also that little matter of the salary cap. Crosby is currently tied with teammate Evgeni Malkin for the second highest cap hit in the league at $8.7 million per year on a five-year, $43.5 million deal that runs through 2012-13. Only Washington's Alex Ovechkin has a higher cap hit at $9.54 million on a monster 13-year, $124 million deal through 2020-21.
Crosby could ask for a new contract that could even top that. Under the current collective bargaining agreement, individual players can make a maximum of 20 percent of the team's overall salary cap. With next year's cap estimated to be around $70 million, that would put the max for a player like Crosby at $14 million a year.
Crosby will be looking to get a deal done this summer before the next CBA is done and more restrictions on long-term deals could be in place, but he's not likely to ask for anything close to that $14 million max. If winning means anything to Crosby — and he's already proven that he's driven far more in the pursuits of Cups than he is in chasing every last dollar available — then he has to leave enough to keep a competitive team around him.
Still, Crosby isn't going to take a pay cut, and he's going to look for some long-term security in exchange for leaving some money on the table. That is where the 10-year, $90 million figures comes in. That gives him a nominal boost to $9 million a year without totally crippling Pittsburgh's cap.
They'll still have trouble keeping everyone together though, even at that number. Pittsburgh doesn't have any key free agents up for new deals this summer, but after this upcoming season Jordan Staal is due for a new contract as well as Crosby, while Malkin and defenseman Kris Letang, plus Chris Kunitz and Brooks Orpik, have deals expiring after the 2013-14 season and goalie Marc-Andre Fleury is up after 2014-15.
Staal carries a $4 million cap hit on his current deal and could be the odd man out. He's in line for significant raise and there's only so much cap space the Penguins can tie up at one position. Crosby and Malkin are indispensible and their new deals will reflect that. It will be a risk for Pittsburgh to deal away a talent like Staal or let him walk in free agency, but as with the injury and insurance concerns, that is likely part of the price Pittsburgh must pay to keep Crosby.
And when it comes to Crosby, the Penguins must be willing to pay any price to keep that kind of generational talent as long as possible.