This year's failure is on Theo.
I'd place the blame on injuries and the players, particularly the pitching staff.
I'd say the majority of the blame should be placed there too although I think Theo made some miscalculations last off-season also.
Theo ultimately brought in the guys that led to Tito's frustrations and thus him leaving.
Lackey, Drew, Youk, Crawford, etc. all underperformed or got hurt or couldn't stay in the team-frame of mind.
You can argue that they were good signings or additions at the time but when you project their production and positives they never measured up and more so they didn't help the team become a team which Francona couldn't fix.
Now we're stuck with guys we have to play or pay and if we play them they will either A. Get hurt, B. Stink it up or we trade them and still pay them.
Sox are in a very tough position from here on out.
Eh, I don't think the situation is really all that bad.
Crawford had a bad year, but he's still young and I think it's safe to say that his underproduction this year was in large part a mental thing. He may never be as great as he was in Tampa Bay, but I expect him to bounce back and be an impact player next year.
JD Drew will be gone, and Youkilis, despite nagging injuries every year, has been quite productive when he has played.
As for Lackey, we won't be able to get rid of him, but I think there's a chance he might be redeemable as a solid end of rotation guy. I doubt we'll see anything close to what we saw out of him this year again.
If the Red Sox get a new manager that can be close to the same caliber as Terry Francona, only perhaps with a slightly sterner, more energetic style, this team may be really good next year. They still have, for the most part, an extremely good roster on paper. The difficulty will be getting them to perform at that level, and shoring up some of the glaring holes (bullpen, getting another top 3 starting pitcher).
Crawford isn't young he's like 31.
He won't be anywhere close to being good as he was in Tampa. His personality doesn't fit with the pressures of Boston.
Youk can't stay healthy for the entire season. Where do they play him? He's a terrible 3B and he can only play 1B or DH.
Lackey might have a better year once he gets passed his personal issues but he still will be over paid immensely.
Who the heck is going to manage this team?
The Sox are basically starting completely over!
They'll still have Beckett, Lester, Buchholz, Pedroia, Gonzalez, Ellsbury, Reddick, Bard, and most likely Scutaro.
How the heck is that starting over?
It seems to me that all the Sox need is another top 3 rotation pitcher (moving Buchholz to 4th and Lackey to 5th), a more reliable group of set-up arms in the bullpen, a new right fielder to replace JD Drew, and to resign Ortiz, Aceves, and Papelbon. Other than that, they could use more depth behind the starting pitchers.
By no means is that a small or inconsequential list of offseason objectives, but neither is it anywhere close to "starting over."