NHL's 5 riskiest free agents

Mike Ribeiro is one of the most skilled centers in the NHL, but he turns 34 this season. G Fiume/Getty Images

NHL free agency is an inherently dangerous exercise. Teams that manage to consistently get the right player on the right contract can add that elusive missing piece for entry into the Stanley Cup contender club. Lock the wrong player in for too much money for too long a time, and not only are you wearing that tie for the rest of the dance, but you likely just tied a competitive anchor around your franchise.

As someone who spent 17 years in NHL war rooms, I can tell you that free agency is an exercise in balancing long-term risk with short-term reward. By definition, free agency is about fixing the now. When a season ends, management typically meets with coaches, players, scouts and whoever else they think might give them some insight into their team. Analyses are performed. Opinions are shared. Potential lineups are written on notepads, whiteboards and cocktail napkins. At the end of it all, one thing stands out -- the empty roster box.

The empty roster box shines like a beacon, wherever it happens to show up, and can be maddeningly difficult to fill. Making a trade to fill that roster spot often ends up creating other empty roster boxes elsewhere in the lineup, or comes with an exorbitant attached future cost (in the form of draft picks and/or prospects). Internal replacement options are typically not yet NHL-ready or are nonexistent. The only short-term solution is free agency.

The peril in free agency lies in the fact that teams are operating in a seller's marketplace. They are the mark at the poker table, only this table doesn't let you see who else is playing or even how much they're betting. (In preparing for free agency, I always felt that a general rule of thumb was to add an extra million dollars and an extra year of term to whatever limits you thought might defy logic).

With the salary-cap ceiling going down and new CBA accounting rules in place, the long-term penalties for being wrong in July have never been more severe. Gone are the days when mistakes can be sloughed off in the minors or loaned to teams in Europe. Long-term, front-end-loaded contracts now carry the ominous-sounding future risk of "cap advantage recapture." Unless a signed free agent is traded, he will count against a team's salary cap in some amount for the duration of the deal. All cash sales are now final. No returns.

With that backdrop in mind, I present you the NHL Free Agency Riskometer, which runs from a reading of yellow (risk is primarily tied to contract length/structure) to red (anchors away). Below are five potentially risky free-agent signings this summer, in order of increasing Riskometer readings.