The biggest free-agent signings are also the ones with the most risk. Teams bid against one another to sign the handful of top names each winter, and thanks to the winner's curse, the team that wins the player often does so by paying for production it can't reasonably expect to get.

For everyday players and starting pitchers, there are nearly always more teams with needs for those players than there are free agents available, which also leads to inflation in free-agent deals, sometimes in dollars but more often in guaranteed years. Here are five of my top free agents from this winter with a look at how each of them might end up wildly overpaid.