The only trade I really have a problem with in hindsight is the Pomeranz trade.
We traded Moncada and Kopech but the return was a strong addition which could lead to the best rotation in baseball.
The Margot, Guerra, Asuaje, Allen trade hurt a little but Margot was redundant and our outfield is fine in Betts/JBJ/Benintendi for years to come. Guerra looks to have been sold high on but Asuaje has taken a huge step forward but we gained a dominant late inning relief arm.
I don't think we gave up anything that will come back to bite us in the ass for the Thornburg trade, none of those guys have high ceilings and I think we sold high on all of them.
Yes we traded away a ton of chips but we got back so much more elite proven talent. We don't need those prospects because this team is set for the next 3 years.
The top guys we still have in our system are in the only areas that may have openings in a couple years in Devers at 3B, Sam Travis at 1B (one sooner than the other).
The Pomeranz trade still irks me, you traded away a potential ace for a guy to help you down the stretch but I was skeptical from day one he could because of his innings. Turns out I was right, not because I'm brilliant but because that seems to be a very predictive and re-occurring theme in the game of baseball.
What DD didn't do was trade away Devers, Travis, Groome, Swihart, JBJ, Betts, Bogaerts, and Benintendi. Lets also not forget that by the time guys like Groome and Devers are in the majors and under team control the Sox will likely extended at least some one or two of Bogaerts, Betts, JBJ. So this "window" we talk about might be closer to 5-6 years than the 3 we are saying now.