I think the differences in Cherington and Dombrowski are glaring. I liked Cherington, but I also doubt the Sox would have Sale or Kimbrel right now were he still here. Possibly not Price, either.
On the bright side, FWIW, the Sox would undoubtedly still have Shaw and Moncada and a slew of other prospects. But Cherington really needed to learn to part with a few, and Dombrowski might need to learn how to hold on to a prospect or two.
I do think you're being a bit unfair to all managers. Sure, very few of them are capable of handling med school. But all of them do understand baseball better than any casual fan. That includes me and you and anyone else on this board. The only executive ever who I felt made stupid decisions that I could have done better with was Jim Hendry, and really, even he made a few very smart moves that I never really thought of.