If I were Cherries......
I'd deal David Ortiz to the White Sox and get 2 prospects in return, top 10 in their system. Ortiz would move Dunn to the outfield, but would make their lineup ridiculous while their pitching got healthy.
I'd deal Ross to the Pirates and try to pry some of their pitching depth away. You won't get Taillon or Cole with him, but they are deep in prospects there and could definitely use a bat for the stretch run. Also, an OF of McCutchen, Ross, and Marte would be pretty nice.
I'd deal Beckett to the Braves, eat a shitload of salary and try to get them to include Randall Delgado. I'd even throw in a top prospect to get him (maybe someone like Brentz). That kid has a high ceiling and is big league ready right now. You could rebuild on the fly if he starts to get it.
I'd look to move all pen pieces but keep Morales. Miller, Atchison, Padilla, et al. No pen piece is off limits, but obviously a guy like Aceves would cost more. Morales would slot into Aaron Cook's spot in the rotation.
I'd move Aaron Cook to a team like the Dodgers. You wont get much in return, but their rotation is trouble in the 4 and 5 slots, and they are relying on Cris Capuano to avoid a meltdown, which isnt likely.
I'd deal Mike Aviles for anything. His slash line is really the kind of player he really is, but his clutch numbers this yr might artificially jump his value. Take advantage now, bring up Iggy and start fresh
I'd also trade Salty to a team in dire need of offense. Maybe include him in the Ross deal to the Pirates and try to see if you could pry a guy like Taillon with that kind of haul. This leaves the sox leverage to sign Shoppach to an extension as your every day catcher. The guy can hit at times, but is a solid defensive catcher, and his time with the club would actually make your pitchers a little better. It would also allow Lavarnway to come up, DH most of the time, but catch when Shop needed a day or two off
This would leave you with...
C- Shoppach
1B- Gonzalez
2B- Pedroia
3B- Middlebrooks
SS- Iglesias
LF- Crawford
CF- Ellsbury
RF- Kalish
DH- Lavarnway
SP1- Lester
SP2- Buchholz
SP3- Morales
SP4- Doubront
SP5- Delgado
It wouldnt clear a lot of money for next yr, but it would definitely inject some youth and some prospects into a system without a ton of depth behind the bigger farm system names.