Well I think Theo said it himself. It appeared to me that he was putting the Lackey signing in the category of things done because you "end up feeling like you have to do something". Clearly he is referring to the feeling that you have to sign somebody, get somebody, add to the roster in some way and how that ends up driving the decision making process.
I did not think Lackey would earn his keep in the AL East for one thing. Second they found out late in the process that his elbow was a problem and still went through with that deal.
So I don't think you need look farther than the comments from the guy that was intimately involved in that deal to determine whether it was right at the time or not. From what I can see, Theo is telling us that if he had it to do over again, he would not have done the Lackey deal.
I also did not like the CC deal from the very start. That does not make me prescient or a genius or anything like that. I did not like the CC deal because I did not see how he was a complimentary player to what we had on this team and because concerns over how he would fair in a big market environment were already all over the place and while my view was from afar, I thought I could see in him a player that would struggle in a big market. In addition that deal seemed to come to the Sox way late in the game as opposed to something that they thought through completely. Finally the price tag was outrageous, way beyond what any other GM was thinking of paying CC and the deal was over such an extended period of time for a player that makes money in part because of his legs. I don't believe you can just anoint a player as someone who will supplement his declining speed with power. You hire a power guy for power and a speed guy for speed and an all around ball player for his all around skills but the idea that a guy automatically will pick up power with age was born out of the steroid era when guys did pick up power but not as a natural consequence of growing older.
However I still think the Sox GM job is one of the toughest in baseball in large part because you have to work for LL and I believe that the pressure to make these "sizzle" signings comes directly from LL. I also believe it to be the straw that breaks the camel's back, making the kind of team profile we have today almost inevitable. As such I have a hard time blaming either Theo or BC entirely for their performance as GM's.