I mean frankly it will be his draft picks and trades that ultimately matter. The Red Sox didn't win a World Series because they signed Carl Crawford. They won a world series because they were able to trade of Schilling as well as bring in multiple core pieces from their farm system(Ellsbury, Lester, Bucholtz, Pedroia...etc). I'm pragmatic about the whole thing. They supposedly spent all the money they had the past 2 years. I have no reason to believe that isn't the truth. Whether or not they should have more money to spend as a big market team is fairly irrelevant.
If I had a legitimate complaint it would be what they've gotten back in trades has often been too far away from the majors. I would have liked to seen them in on someone like Fister and Dexter Fowler. Their A level players last year were quite good but realistically you're looking at 2 years before those are ready for the majors at the earliest. As such, they are sort of in this weird position where they don't want to be a complete sell off because they need averagish players around when bigger stars come up to make them a half way respectable team but at the same time they aren't going to be good enough to legitimately contend for the playoffs for 1-2 years. That's how you end up with guys like Bonifacio. He should be an average-ish player but there is some potential there if he plays up to his 2011 level.
Ultimately, that was the biggest regret from the Hendry regime for me. It's great he drafted guys like Baez and Alcantara. But the talent in AA/AAA when Theo and company took over just hasn't been very good. Whether that's fair or not to him is inconsequential to me really because thus far what they've pulled out of the minors the past 2 years has been pretty slim pickings. You're talking about Castillo, Lake, Valbenuna, and I guess just Rusin unless I'm missing someone. And since the Theo regime has been unwilling/unable to trade for pieces closer to the MLB level you've end up with some fairly bad teams.
