How would DD have handled the Betts trade mandate, which he apparently came close to doing during 2019 AND also a massive cut to the budget for 2020 with small incremental upticks in winter spending for the following 2-3 winters?
I think he saw the writing on the wall, and that's why the friction happened.
The part about no trading top prospects for 5+ years might have been the final straw.
There is a good chance DD or any other GM might have done better than Bloom- both with farm and 40 man roster building and MLB team success from 2021-2023, but it's hard to know.
Here are the top ranked prospects (soxprospects.com's ranking when traded):
16. Jay Groome summer '22 (Rosier)
9. Aldo Ramirez summer '22 (Schwarber)
Unranked T Lakins Jan 2020 (J Springs)
9. CJ Chatham fall 2019 (PTBNL)
6. Beeks summer '18 (Nate)
19. Ty Buttrey summer '18 (Kinsler)
Unranked S Espinal summer '18 (Pearce)
16. S Anderson + GSantos summer '17 (Nunez)
Only Beeks was top 8 going back along time.
You have to go back to the winter of 2016-2017 to find a top 5 prospect traded by the Sox:
1. Moncada, 5. Kopech + 7. Basabe (Sale)
10. Dubon (Thornburg)
July 2016: #3 Espinoza (Pomeranz)
Nov 2015: 4. Margot, 6. JGuerra, 13. L Allen (Kimbrel)