I'm confident they'll resign Damon. I like Millar's clubhouse presence, but unless he's okay with a backup job or a HUGE cut in pay, he's gone. He's a great guy, but not worth the asking price. Graff should be resigned, with Pedroia backing him up at 2nd. Timlin should re-sign, unless he retires.
If the sox can go into next season with Damon, Renteria, Ortiz, manny, Tek, Trot, Youkilis, and Graff then there won't be too many spots to fill and they will still score a ton of runs.
Also, sign Burnett if possible. Schilling, Burnett, Wells, Clement, Papelbon would be a great 1-5, with Wake either in the pen or retired.
What is the liklihood that some of these older guys might retire if the sox win it again? It seems likely to me, but that's pure conjecture.