As I've always said, I'm fine going all in, when the window is open. I do think DD went a bit overboard, but the results negated the long term negative impact, IMO.
The Phillies are in the WS. Already, it has been worth any sacrifices he made to the future. The bigger point is that he has not significantly hurt the farm by getting them there.
The Castellenos deal may look bad, right now, but it was $100M/5 not $210M/7 like Price. Schwarber got $79M/4 not the $145M/5 Sale got. There is "large and long" and then there is larger and longer.
He inherited some other bloated contracts, but he's getting production from all of them- Harper, Realmuto & Wheeler. Something DD was not getting from HRam and Pablo, when he took over BOS or what Bloom was getting from some of the big contracts he was handed.