This is an excellent thread. Lot's of good ideas from everyone.
This off season will be huge. Theo has his work cut out for him.
Speaking only about what the Sox should/could do with the outfield, the situation is complicated by the fact that the Sox are comited to CF and RF at $22. Mil. through 2011.
I think the Sox should try to move Cameron (paying a large part of his tab). He's just not what is needed at 38-39 years old coming off surgery. Eat the mistake. Drew is not going to sign with what he will want next year and that's good. Move him too. That won't be easy. But if the Sox swallow half of his money, there is a possibility.
Now, grab Crawford for left, Ellsbury in center, Kalish in right.
Or, assuming that Drew can't or won't be moved, trade Ellsbury for someone of impact and have Drew play his contract out.