I think Boston ownership is confronted with a dilemma. Ricketts is going to offer Theo his dream job (albeit in Chicago, not Boston). Boston can offer him an extension and more money, but can they promote him substantively vs designating a fancier title? Unless Lucchino is ready to ride into the sunset, I'm not sure they can. Doesn't mean that it will happen, and Theo could be using this as leverage in Boston. Still, Ricketts will land one of his top picks. If you pass up an opportunity like this, you may never get another. Here's the thing though. Theo is established in Boston, beloved by the ownership and has a long rope with the fans even if they are antsy about the last 2 seasons. He also grew up in Boston as a Red Sox fan. His original dream was likely to play for the Red Sox, and then be the GM for the Red Sox when his athletic dreams died like they always do. The Red Sox hold a significant advantage there. He may not be able to get a higher title right now but if he sticks around Boston long enough he will get the opportunity most likely. He's not even 40 yet so he can afford to be patient. Have you seen what the public sentiment has been? Not just the insane people who comment on blogs and articles, either. The fan base seems to be indifferent at best on him leaving. The radio call in shows have been somewhere along the lines of the blog comments, too. I've listed to the radio shows. A majority seem to be ok with him leaving but aren't exactly running him out of town. Most of them respect that he was able to bring two titles and wouldn't be upset if he stays. You are right that they aren't flipping out saying 'we've gotta keep Theo' but given that they are 8 days removed from a historic Red Sox collapse that kept a heavily hyped team out of the playoffs, I can understand fans being ok with change even if it involves their highly regarded GM who has brought them 2 titles in the last 8 seasons. What's the sentiment next year if the Red Sox fail to make the playoffs again? Or even if they can't make it past the divisional round in the playoffs? They won't have Tito to throw under the bus to sacrifice to the mob the next time.