Quick thoughts on some of the more controversial moves:
Matsuzaka: Loved this move and still do. One of the best days ever honestly when I found out we won the bidding and then later when he signed the contract. I'll talk about this with Drew also, but the cost was "only" money, no draft picks or prospects and we landed a 26 year old with great stuff. He was probaly hyped a bit too much. Ace? eh idk, its possible but I think realistically he is a #2 or #3 which I have no problems with considering we have Josh Beckett and even Clay Buchholz in the same rotation. I'm hoping for some big strides next year, realistically I think he is a 200+ inning, 3.70 ERA, 8.3 K/9 and hopefully get his BB/9 into the 2.50-3.00 range which I think is definetly a possibility. People talk about the 100 mil comittment, but I believe all of the 50+ mil owed to the Lions is already paid off, so we owe him 48 mil or so over the next 5 years, love it.
Drew: Again I loved this move. He was coming off 4 straight years with an OPS over .885 and again we didn't have to give up any draft picks or anything. Hopefully he bounces back next year to at least a .840+ OPS. He wasn't completely useless as some people make him out to be, ~.800 OPS with a .370 OBP. He's sound defensively with a good throwing arm.
Lugo: I'll admit I was for this but I really hate it right now. We owe him 27 mil over the next 3 years and lost our chance at drafting Porcello. And to add insult to injury, we have a fine young 'SS' prospect in Jed Lowrie who is just about ready and has a nice bat. Hopefully we can pawn him off on someone somehow. Looking at his career numbers I can't justify giving him that much money even if you throwout this season.
Gagne: Again I don't think there was many opponents of this deal when it happened. It didn't work out at all, but you can't fault Theo for going out and getting the best MR on the market. We didn't give up anything major either. Gabbard looked like a servicable SP, but his success in Texas was limited and his peripherals are going to catch up to him. Murphy looks pretty good too, I think he could possibly be a .780 OPS OF over a full season. Beltre I didn't like giving up, but in 6 years, if he makes the majors and is an all-star you just tip your cap. We drafted Mark Texiera 9 years ago but I've never shed a tear over not signing him.
I may be a Theo apologist but I love what he has done with the team. The farm has been amazing, and the overall talent on this team is great. We had the best record in baseball and are in the ALCS, not much you can do when everyone in your lineup and nearly everyone in your rotation lays an egg in the 2nd series.