Theo would have been better off he hadn't sign Crawford and Lackey, and instead signed Beltre, and kept Youks at 1B. And not trading for Gonzo (though it was a helluva good deal for Boston). He should have re-signed VMart and used him at 1b and DH--much like the Tigers are using him. He would have been better off signing Werth, who was bound to have a better year in Boston than he is in D.C. But then he didn't know that Ortiz would comeback to close to his hitting form of a few years ago--so he was looking for a left handed power bat in AdGon. He also didn't know Lackey would be a different pitcher from LA, but Lackey's poor record at Fenway against the Sox should have been a warning flag.
Signing Crawford didn't make much sense to most people at the outset. Though nobody knew Ellsbury would come back and break out, and basically marginalize Crawford's worth to the team.
Lots of things happened, and none of it good for Theo.
The bright spots were Salty and Buchholz. Plus comebacks by Papi and Ellsbury. You don't know if Ortiz will sustain it. I doubt it. Both these guys are playing for bigger contracts. Buchholz kills them by being out most of the season. Youks gets worn down with injuries trying to play 3B. Finally, Salty is given a catcher's nightmare--catching Wakefield--a pitcher who has harmed their catcher development in recent years--hardly worth the climb.
What will happen next year? Crawford and Lackey will be on the trading block. Papi probably won't be re-signed. Hopefully, Gonzo's should is OK. Other players gone will be Wake and Tek. Tek should be the bullpen coach--maybe the manager if they kick Francona upstairs. Pedroia will be the Captain, and will be given the authority to kick ass if anybody isn't in shape in spring training. The pitchers will now be told to hold runners, and team fundamentals will be stressed.