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.
To get Craig's take on Roberto Luongo, Sidney Crosby and other key contract situations, you must be an ESPN Insider.


