Why would Henry feel wounded by the Crawford deal? It was actually a good idea for the Sox; it just didn't work out. But at the time, Crawford was coming off an MVP-caliber season, and the Sox probably suspected re-signing Ellsbury would not be easy, as he had rebuffed several extensions and his agent (Scott Boras) was notorious for advising players to go to free agency. To me, it looked like an early attempt to replace Ellsbury at the top of the lineup with an elite leadoff hitter. Sort of a pre-emptive strike, and probably smarter than waiting out Ellsbury and settling for whoever was the second best leadoff hitter the following season. The idea was good; the results were not.
I doubt Theo comes back. Right now, a return to the Red Sox is a lateral move at best. Why goi from being President of Ops of one large market team to President of Ops of another, and one you have already worked for? If Epstein goes anywhere after Chicago, I would expect him to try a different challenge. When your reputation is for ending long standing title droughts, who is next? you ended the two mot famous ones already. He might have to try to end a smaller market one. Like Cleveland or Seattle.
The Sox might even consider just promoting Assistant GM Eddie Romero. He's been with the organization a long time and is from a baseball family (dad played for the Sox). And if Henry wants someone he knows, Romero certainly qualifies. The Sox have certainly had no issue promoting internally to GM before, with Epstein, Cherington, and the oft-forgotten Mike Hazen.
In fact, during Henry's tenure, the Sox have had six GMs. He inherited Duquette. Mike Port was an external hire from the Arizona Fall League, where he was President, but he had some GM experience with the Angels. (The Sox later promoted Port to VP.) Epstein, Cherington and Hazen were all internal promotions. And then Dombrowski, who has the dual title of President of Ops/GM, and who was really hired to replace the recently fired Larry Lucchino for the former position, but took over the GM role when Hazen accepted the Diamondbacks GM position.
So really, internal promotion seems to be what his history dictates...