At the end of the day, we traded a lot of bodies, but quantity does not equal quality. One issue I have with the "cliff" and "depleted farm" narratives is that they make it sound as if keeping all those guys around would have vastly improved our long-term outlook, which I think is far from evident. If you think we're headed for a rough patch somewhere around 2020-2021, then I doubt still having Manny Margot, Javier Guerra, the Basabe brothers, et. al. would change that much.
Meanwhile, the White Sox trade where we did give up the most quality could end up the biggest win of all, given how incredible Sale has been and the uncertainty that still surrounds Moncada and Kopech.
Speaking as someone who fully admits his own bias towards building through homegrown talent, Dombrowski's trades have by and large been shrewd ones, and as I've said before, he's showed a discretion and patience at times (see his refusal to trade Benintendi or Devers, or putting Bryan Mata off limits in the Sale talks even before he was on the radar as a serious prospect) that has impressed me and really puts the lie to his "Desperate Dave" reputation. It's tough to find a whole lot to go back and quibble with, particularly as we enjoy watching what may well be the first 100-win Red Sox team in most of our lifetimes.
Of course, it seems Dave will ultimately be judged by whether he delivers a title in the next several years, but for the moment, it's hard not to see his body of work in Boston as overwhelmingly positive.