I'm not the biggest DD fan in the world, but he's a shrewder trader than he's often given credit for. At both the 2016 and 2017 deadlines he held his fire rather than pushing for a larger move because the right trade wasn't out there (in the former case, waiting until the offseason to get his target, Sale, when the price was less extreme). Dealing Espinoza for Pomeranz currently looks like a winning bet (although I'm still hopeful for Espinoza's long-term future), as does keeping Devers over Moncada. There were reports previously that the White Sox wanted Bryan Mata in the Sale trade talks and Dombrowski refused to include him, despite his then being a 17-year-old who had only pitched in the DSL and wasn't on most people's radars.
Our prospect list has certainly taken a hit, but how many of the guys we traded will actually end up coming back to bite us remains to be seen. Right now trading Travis Shaw looks like the only outright blunder...but again, time will tell.