Since 2004:
Good Theo :
1. Let Pedro go.
2. Let Damon go.
3. Draft Ellsbury/Bucholtz.
4. Get Matsuzaka (even with struggles best free agent starter with economical salary - if you do not consider posting fee).
Bad Theo:
1. Getting Drew.( # 1 in my list at this time - may be he will turn it around).
2. Letting O'cab walk and getting Rent here and getting Lugo here( I know Lugo turned it around - still I like O'Cab).
3. Trading Arroyo - he is not good but we got nothing from that trade.
4. Byrd/Meridith fiasco with San Diego for a guy whose only qualification is he can catch knuckleball.
5. Let Carlos Pena walked - Yeah I know noone saw that etc. - still it is in my list.
Feel free to add whatever I missed. I would say it is 50/50.