Seems to me, as many have said before, it's all about the LT cap. Even though Lucchino said they would more than likely go over, and some posters have calculated that we are already over.. I still don't think there is enough room on the payroll to sign someone like Oswalt. In my opinion getting a solid starter is way more important than getting another outfielder. Yes, I know we are LHH heavy, and no one wants to see DMac starting in left or right for that matter, that in my mind is still secondary to the rotation. The rotation wins games, not the outfield corners.
That said, Cherington himself said he would have to move payroll to make room for someone like Oswalt. I personally think they are trying to look out for the future of the Red Sox, not just the 2012 Sox. Even with the top three of our rotation we have a decent staff, it's not the best, but it surely isn't the worst. Even with the shred of rotation that we have, our offense will help us win a lot of games for sure. There is no question about that.
I believe that the Sox are "rebuilding" in a way, and by that I mean they aren't just throwing money at free agents to win right now. I would like to see them win, as would any Sox fan, but I'd like to see them win without having to damage the possibility of winning in the future. Our payroll is already handcuffed due to large contracts, and I don't think it should get any worse. Not to mention the percentage that would have to be paid on the LT would probably affect their ability to make future signings.