I still think the Dodger dump trade was one of the best deals any Sox GM ever made. He helped purge Theo's mistakes and make the team able to compete for many years afterwards.
Uehara was maybe Ben's best get and re-sign.
Also, I'd say the one year deal with bonuses attached for Napoli in 2013 was better than the Vic deal.
He also trade Lowrie and Weiland for Mark Melancon.
The Cody Ross signing was very good.
Other good deals:
Lars Anderson for Steven Wright
Signed Rich Hill for dirt- twice.
Acquired Mike Carp for cash.
Signed Int'l FAs: Moncada (C Sale), Manuel Margot & J Guerra (Kimbrel), both Basabes, T-W Lin, and others- many used in trades by DD.
Drafted & signed: Benintendi (7), Marrero (24), M Chavis (26), B Johnson (31), M Kopech (33), S Travis (67) and several others- many used in trades by DD.