Wow this thread got long while I was away. Well anyway, I rated him a B.
I think what many people are ignoring here is the sheer number of holes the team had. If you compare what the team had at the end of 2011 to the beginning of 2011 offseason, the team need to replace three big-inning starters (Dice-k/Lackey/Wakefield), three relievers (Papelbon/Jenks/Wheeler), a big bat (Ortiz), a RF (Drew/Kalish) and a catcher (Vairkek).
The good: Picking up Cody Ross for 3 million? Huge bargain. Picking up a catcher with a good arm? Finally! Andrew Bailey and Melancon for Reddick, Lowrie, and scraps? Exceptional deals. Nick Punto? A solid defensive replacement for later innings is fine with me. Loading up on depth signings
The bad: Paying Ortiz 14.5 million. If you have limited resources, you really cannot waste money on a lumbering oaf. He would have tested the market and come crawling back for a 1/10 or 2/18 deal.
The ugly: Trading Scutaro for nothing. It makes this team look cheap, and noncontenders. Try to compete in 2013, okay?
The really ugly: No #5 pitcher? Are you crazy? Instead of getting money for Theo... you got Christina Carpenter. Great work there. Oswalt sits on the open market waiting for a fresh offer.
The truly terrible, horrible thing: Jed Lowrie is gone
There is a lot of ugly. But in all fairness, Theo and Larry let this ship sink to the bottom of the sea.