He did choose well on who to keep and who to trade. I'm not sure how much was being "astute," but GM are always bashed in hindsight, so it make sense to praise them when things work out well, in hindsight, too.
The sheer number of top or once top prospects trades was astounding, but I've never felt he "emptied the farm" or left it "barren."
I loved DD and had no issues with the choices he made to sacrifice some of the extended future for a nice 3 year window (that coulda-shoulda been longer.) The fact that we went from the Devers call-up in 2017 to the Casas and Bello call-ups in '22 & '23 with no noteworthy farm infusion beyond Houck has to fall, at least partially, on DD's shoulders. That being said, he did keep and or add: Devers, ERod, Bello, Casas, Houck, Crawford, Rafaela, Beni and Mata, Wikelman, Perales, Murphy & Walter (a large chunk of our best pitching prospects.)
Traded prospects (w top SP's ranking)
1. Moncada, Swihart
3. Espinoza, Margot
5. Kopech, Beeks, RanaudoCecchini
6. Guerra, Brentz
8. Basabe, Chatham
9. Dubon, Lakins
12. W Rijos, Marrero
13. Logan Allen
15. Light, Longhi
17. S Anderson, Buttrey, Jerez
18, The other Basabe
19. Acosta
20, Nogosek
Espinal, Gregory Santos, Aro, Asuage, G Bautista, Callahan, Pennington, TShaw (not a prospect, when traded)
Note: I am not trying to inflate the value of these guys traded away. Many were traded after they dropped out of the top 10 or 20. My point was to show the numbers of prospects traded away.