Now that Larry is out of the pitcher, I just hope baseball ops is autonomous enough to make all decisions and not be coerced into flashy signings like Crawford, Hanley, Panda, etc.
If Theo didn't leave in a gorilla suit, they wouldn't have made the Beckett/Lowell trade and most likely would not have won in 2007. We really have no idea how much Larry pressured Theo into the 2011 signings. However, Theo has set the Cubbies up for ling term success. Has Ben set up the Sox in a similar manner? That remains to be seen. Ben did great with the MILB rosters, but struggled in putting together a 40 man roster that could compete every year.
Honestly, I doubt any GM's are significantly better than all of the others. It's more about organizational philosophy and the size of the checkbook.