When people say "Theo", "Ben" or "Dave" it's really just short hand for all of the front office while that GM was in charge. We'll never know to what extent Theo wanted to "feed the monster" or if it was Larry, or if Ben wanted to sign Panda or if it was ownership, or if Dave is pushing the fire sale of the farm system or if it was directed from above.
At the end of the day, those three guys each have good and bad things about them, but Sox fans have been lucky that they've at least been fairly competent.