I started a post along these lines but deleted it. Then I saw this and figured, what the hell. I think a package of WMB and a couple of pitchers for Masterson might make some sense. Indians get a 3b prospect with more upside, and two good future pitchers (they hope).
Sox get another top shelf, young SP, and they just go Drew/Bogaerts on the left side, with Cecchini in the wings for the eventual Bogaerts/Cecchini left side. Masterson is a FA in 2015 so the Sox would have to fork over some money for him, but I love the prospect of Lester/Masterson/Buchholz/Lackey/Doubront, with Peavy and Dempster moved for prospects to replace the ones they just gave up (though they'd be of lesser quality).
EDIT: But the more I think of it, I'm pretty happy with the Sox as currently constructed. Very good rotation, quality (and improved) bullpen, Napoli back, JBJ taking over in CF, Bogaerts/Middlebrooks at SS/3b. Probably won't win 97 again, but that's a really good team again, and fun to root for. And we keep all the young'uns.