He was never on the bandwagon.
Pena cost Arroyo, not a huge loss. No argument on Gagne, Lugo, Clement. Wakefield wasn't a Theo move (really now). Casey wasn't a bad move. He got tons of value out of Timlin. Colon was a low cost move. It didn't hurt. If you wanted to remain incognito maybe you should have picked new players to hate.
Looking at his GM history, here are some moves that helped the team:
Bill Mueller
David Ortiz
Keith Foulke
Hideki Okajima
JD Drew
Daisuke Matsuzaka
Todd Walker
Kevin Millar
Gabe Kapler (he helped and cost nothing)
Curt Schilling
Mark Bellhorn
Dave Roberts
Trading Nomar for Mientkiewicz and Cabrera
Mike Myers
Not enough? How about draft picks: Jonathan Papelbon, Dustin Pedroia, Jed Lowrie and Justin Masterson. Plus the jury is still out on Buchholz, Bowden, Ellsbury, Lars, etc.
Of course he won't.