What's the cost though? Who would they deal that has a huge shot at contributing significantly over the next 3 seasons anyway, when they should be making a sustained push for repeat World Series?
Weiland? No. Lavarnway? No. Even Reddick--though very good this season--has Kalish behind him. Middlebrooks? No. Iglesias, Brentz, Navarro? No, no, no.
The Sox are in the enviable position of having nearly every position player and an entire rotation locked up for the next few years. They can resign Ortiz and probably happily deal with a Lowrie/Scutaro combination even for another year if they need to.
I think the Sox are about to the get to the point where only the true superstar potential prospect becomes "untouchable", and everyone else is available. Some think Theo is just blowing smoke, but i agree with him that this is a very deep farm right now with lots of upside. They don't have the sexy prospects they did a few years ago with Ellsbury and Buchholz potentially available, but they have enough to provide MLB regular caliber players while not even hurting the team's depth that much.
How much would it really hurt them for the next few years to move Weiland, Doubront and Middlebrooks for Ubaldo? It might limit some options, but they would solidify their rotation significantly. I can see why they would be serious about kicking those tires, especially to keep him out of NY.