To build a winning team, you have to take risks. Risky contracts aren't necessarily bad ones, but rather deals that can make all the difference if they're successful and leave a team holding a very expensive bag if they aren't.
While some of today's long-term deals might blow up down the road, these selections are based only on which contracts are riskiest right now in the 2013-14 season. This is based on the salary information from Cap Geek and GVT data from Hockey Prospectus.
What is GVT? It's a high-level estimate of all of a player's overall contributions. Based on the player's current GVT, and what is expected the rest of the way based on his recent performance, the shortfall is calculated by looking at what that level of production normally costs relative to the player's actual cap hit.
The common theme throughout this slideshow is the risks teams will take to sign a reliable top-four defenseman, a veteran two-way forward or some stability in nets. Turn over to see the riskiest contract on a team-by-team basis, in alphabetical order.
All advanced statistics are via writer's own original research unless otherwise noted.