I understand that Drew was the best player available on the market, but considering who is available in terms of outfielders after this season, wouldn't you have rather waited (Hunter, Jones, Rowand, and Cameron)? There were a lot of people against the move when the Red Sox signed Drew, and it is becoming quite clear that those feelings were warranted. Why couldn't Theo see this coming?
Honestly, take a look at his offseason this year. J.D. has been an awful signing. Although he's come on a bit lately Lugo has been a horrible signing. Dice K, although impressive at times, has been extremely inconsistent so far this year. What really worries me about Dice K is that historically Japanese pitchers imports pitch there best in when they first get to the MLB.
Theo has been awful since the championship year, and he has got to go.