That is a good question, and the hindsight does seem to say "NO WAY," if you figure we needed the trades to get the 2018 ring. (I think we did-many of them, anyways.)
It's hard to imagine us winning it all without everyone he added, but one could easily argue we might have without several of the moves. Some players weren't even all that good in 2018, and some did poorly in the playoffs.
Although almost all the prospects we traded are having bad seasons, this year, their control time is still going on many of them.
If one can argue we could have won without Sale, then surely one could think we'd be better off with Moncada and Kopech, even if we might have traded them, later, for something good.
I'd like to have Margot and Allen, now, but neither looks all that great, now. Kimbrel did great for us, but we likely would have made the 2018 playoffs without him and his playoff performance left a lot to be desired.
Pomeranz did very little in 2018, and could easily be viewed as a negative that year, but Esperanza has been hurt forever. I'd still like to have Espi in our system than not.
The Thornburg and Smith deals looked good, at the time, but if we are looking in hindsight, they did not work out. I'd like to have Dubon, and Travis Shaw played well for a stretch after the deal.
I see what DD did. He went for broke and built a team that could win despite having off seasons or horrific playoff performances from several stars. That's one way to insure a ring- overkill. I said all along, I was fine with what he was doing as long as we got a ring, and we did, so I'm not going to roast him for doing it. However, I also knew at the time, that he was sacrificing our future for a 4-5 year window. I was fine with that then, despite the fact that we didn't really get 5 great years. We got the ring, and DD was a big part of getting it.
I'm not going to sugar coat the fact that he's also a big part of why we are where we are now- the cliff.
It is what it is.
It was what it was.