Each offseason, teams make huge investments on free-agent players who all come with their share of risk factors. Whether it be a potential decline in skills due to advancing age—most players don't hit free agency until after their 30th birthday—or injury concerns, there is always a chance a free-agent signing is a bust and ends up on a list like my "Worst Free-Agent Signings of the Last 10 Years".
Taking a cautious approach is absolutely necessary, although a team will ultimately be making a gamble. A player's market value is set by previous performance and it takes 30 teams to ignore that value if the player is going to make any less. And it takes just two interested teams to start a bidding war and boost that value.
The Red Sox took the chance that they'd lose free-agent Mike Napoli last winter, pulling a three-year, $39 million deal off the table after tests revealed avascular necrosis, a degenerative hip condition that made a multi-year deal risky. Ultimately, the 31-year-old decided to sign with the Sox, taking a one-year deal with a guaranteed $5 million and a chance to earn another $8 million if he can avoid the disabled list.
It's worked out for Napoli and the Sox so far, as the player has remained healthy and has been productive. If not for 29 other teams that decided not to swoop in and sign him to a multi-year deal while the Red Sox were trying to re-negotiate a lesser deal, Napoli would likely be playing elsewhere.
This is just one example of how teams are wary of getting stuck with "dead money", meaning a guaranteed salary for a player who is producing very little or nothing at all.
Here are six soon-to-be free agents that have likely earned long-term deals but might not be great long-term investments.