Kinda-sorta, but not a top 3-5 farm like the Sox reached under Bloom-Breslow.
Also, would he have stood for what Bloom did? Trading Betts was one thing, but not only was his contract cost not replaced, there were further cuts down the road for 2-3 more years. We never replaced JD, Porcello, Price, Nate, ERod and other rather large contracts. I guess we can say we tried to replace Bogey with Story, but that's it. Every stud we lost from the 2018 team was not replaced, in kind or nearly in kind.
While several prospects DD did not trade went on to do well, Devers, Houck, Duran, Rafaela, Crawford and Bello, to name a few, many took years to make an impact. Maybe DD would have drafted college players over HS players and saw a quicker ROI, but I doubt he could have rebuilt the farm better than it ended up being rebuilt, especially if we won more, which is your premise, and had lower draft picks.
No Mayer draft slot.
Maybe no comp picks (Anthony & Campbell)