It's February 15, the day after Valentine's Day, and Roy Oswalt is feeling the pains of unrequited love. Solace won't come in the form of discounted candy this year, as he's set and specific in what he's looking for in a partner; without that perfect match, what's the point in pitching?
It's not that Oswalt has limited himself to just the one option, as he would gladly pair up with either the Rangers or the Cardinals, or maybe even the Reds if they would just give him the time of day. It's just that he's spent the winter looking to get with those who already have found the pieces that fit them, and he's hoping, by waiting his options out, they'll realize that Oswalt is just a better match for them. The phone didn't ring once yesterday, though, making yesterday another day just like today, and tomorrow looks to be no different.
With all of his co-workers excitedly packing up to head off and be with their own teams, one starts to wonder if Oswalt is just going to have to settle for the first that comes courting. Maybe this isn't where Oswalt envisioned himself, but when spring rolls around, does he want to be alone, or does he want to share in the beauty of that time of year with someone else who does appreciate him?
It's very rare for a major free agent to have failed to sign by truck day. It's not that rare for a player to wait until January to sign a mega-deal -- Vladimir Guerrero, Carlos Beltran, and most recently Prince Fielder have all done this, as have others -- but cases like those of Oswalt don't come around often. In 2003, Ivan Rodriguez signed a one-year deal on February 6 with the Florida Marlins for his age-31 season. He was one of the final pieces of their championship team that year, and gave them his customary defense and a 120 OPS+. The Red Sox would very much like Oswalt to be their Ivan Rodriguez.
Bill Parker of The Platoon Advantage looked at how few free agents worth their names signed after this date. You should read the piece in full, but Parker essentially broke down these late signees into three groups: the great but very old, the injury prone, and the last resorts. Oswalt doesn't quite fit into any of those camps, as he's great but not very old, potentially an injury risk but not exactly injury prone, and certainly not a last resort given he's still capable of greatness.
Parker found two who didn't quite fit the bill in the same way Oswalt doesn't in the form of Tony Fernandez and Greg Maddux. Add those two together with the Rodriguez mention from above, and you can see that in the last 20 years, this kind of thing just doesn't happen very often.
Oswalt might be waiting for the Rangers or Cardinals to clear money or a roster spot. The Red Sox are waiting for Oswalt to realize that this just isn't going to happen in 2012. You can't count out either the Rangers or Cardinals entirely, but depending on them to make a move or moves in order to accomodate Oswalt is no sure thing, and while the Red Sox look to be dealing with an unrequited love situation of their own here, Oswalt might eventually realize that there is a worthwhile match here, even if it isn't what he's dreamed of. At least, that's what Boston's mid-February hopes are made of.