I think you are missing my point.
Those last 3 (and Lowrie, Bard, Caleb Clay) are the types of players that can make a GM's career, if the GM is still around when they are ready for the highest level. You were quick to give Duke credit for his drafts, so I think Theo deserves the same treatment.
When Theo took over, the farm system was completely depleted of impact talent because Duke used prospects like currency. Letting the big name FAs walk gave the Sox 7 extra early round picks the last two years. Early rounds are where the potential impact talent comes from. I think they made the decision to retool the farm system as soon as they won a championship. When you let one FA walk while replacing him with another, you still net a pick in the supplemental round. I think the goal was to take advantage of that loophole. They went out, spent the coin needed to put a championship caliber club together, and won it all. After that, they have some leeway with me to restructure.
Like I said earlier, I think the fanboys overrate him, but the second guessers do just as bad a job underrating him. Well, at the very least, they don't read between the lines and look at the motives/long term goals that some decisions indicate.