@AR
Theo could not have predicted that Crawford would be awful this year. his performances in the past warranted the contract. Theo also could not have forseen injuries to basically the entire Sox pitching staff. the signing of Lackey was bad, but no worse than Burnett and the Sox can easily absorb that kind of money. what hurt him the most were trades for the likes of Gonzalez, which stripped the farm of ML ready talent in case of a situation like the Sox faced in September, when every pitcher was not pitching well and the bullpen was a mess. of course, they got Adrian Gonzalez and his 6.4 fWAR this year and for many years to come. I'd say they'd do that trade again if they could.
they have home grown talent Ellsbury, Pedroia, Lester, Papelbon, Bard, Youkilis, A-Gone (gotten with home grown talent)...you're telling me they shouldn't be flexing any of their massive revenue advantage over 99% of teams? they are not really getting old, either. Ellsbury, Pedroia, Lester, and Bard are all still well under 30.
the Sox just ran into a perfect storm of bad luck. Theo is a fine GM.