Well, I agree with the people who say the Phillies didn't hire Dombrowski to rebuild. They just signed JT and are all-in to win for at least the part of his peak years that overlap with Nola's contract. Dombrowski is supposed to fix the entire organization but he made it clear that he intends to win with the talent that is already here, and perhaps even believed in that more than Middleton, who was at least ready to cut payroll (and even go a season with an interim GM, supposedly).
I might think a rebuild is a good idea but I also dont think there's any chance of it happening. You can see it's not even the most popular idea on this board, which is pretty forward-thinking and prospect-loving, so imagine how it would play on WIP or at the ticket window.
I do still think Klentak would have gone with a slower rebuild. I'm not sure that would have helped too much given how poorly they wound up drafting and developing, even with higher or more picks (though both certainly would have helped). But the 2018 moves that were meant to simply stabilize the team made them too good, when they clearly would have been better at least being sellers - could have flipped the relievers and Cesar at least - if not a Top 5 drafting team again.
The most depressing thing to me is that we've been through two waves of disappointing young talent already. We have Cutch because Williams (and to some extent Altherr) failed, we have Segura because we gave up on Crawford (and then had to get Didi because Segura can't play SS) and now the same thing has happened with Haseley and Kingery (at least for now). The only surprise is the return of Herrera, which I was never especially in favor of, but having been proven wrong now you have to wonder why he wasn't playing, or at least at the alternate site, last year.
I can remember many a year, especially in the '90s, where the only way the Phillies would be good was if every player had a best-case scenario season. Back then front offices weren't as savvy about the age curve though.