Roy Oswalt has decided to remain unsigned until midseason next year and hope to sign for a contender. He has been increasingly difficult and trying to sign with a team throughout this offseason, turning down a multi-year offer from the Pirates and not listening to some teams offers. He has chosen the way he wants to go, and miss some paydays until midseason when he can hopefully find a roster spot with a contending team.
He had very good splits when coming back from injury in late August and September, and could have probably found a contract with nearly any team if he didn't keep his asking price so high. He is missing out on a potential payday, but I don't think he cares as much for the money as he cares that he might get the chance to go to the World Series. I don't think this is a good decision, but it's what he wants to do, and maybe he might be able to land a contract with contending team as a starter midseason and carry the weight, from what I am guessing will be from an injured pitcher. I don't think it will be good unless he is pitching in an independent league, because he might have to undergo a small stint in the minor leagues before he is ready to face major league batters again. I predict that he may be with the Red Sox by the trade deadline due to the recent need for pitching from Boston.
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