I think you can make a pretty solid case that Dombrowski had very little choice but to do what he did, or to do something pretty close to what he did, for this team to have any shot in 2016 or 2017. The pitching staff left to him by Ben shaped up as horrendous, and there wasn't a lot of payroll room to work with either. What else can you do but trade for pitching?
Dombrowski did try to make use of one of the few 'semi-proven' pitchers left to him by exercising the option on Buchholz, and Buch naturally bombed, necessitating the trade for Pomeranz.