I just got off the phone with Theo. He disagrees with your assertion.
It's nothing personal. I just find it a bit interesting.
I think my view of Theo is similar to my view of Tito. There were clearly things that he did wrong, but there was a lot of behind the scenes things that he did right. Like even JH and LL said today, this team has averaged more wins than any other team besides the Yankees during his time there. That could be attributed to their payroll, but that would be a bit naive, given that other teams with high payrolls have dipped up and down in terms of wins while the Sox have remained largely consistent.
Also, like I said (somewhere), there's a lot about how Theo managed the organization internally that deserves respect. The development of actual systems to ensure consistency of approach, strong drafts, excellent FO personnel recruitment and development, etc., are not things to be taken lightly. Like Tito, he was a person who made others want to work hard for him and to achieve at a very high level. Easy to overlook but essential in a place like Boston.
Just as Tito often took the hit for his players and managed to keep clubhouse issues in the clubhouse (despite some very big egos), Theo (and this ownership/FO in general) managed to do a lot of things behind the scenes well to buffer the drama-potential in the city, and that's one of the things that makes him generally regarded as an excellent GM. Revenues went up significantly and this is now one of the most lucrative teams in sports. Some of his most high profile moves haven't panned out, but if this team had made the playoffs over the Rays they would have had the highest proportion of their wins from homegrown players of any team in baseball. That's pretty impressive for a big market team.