Hard for me to buy that the Casty signing is actually a bust given the team's overall performance. He was a clear positive last year (including in the post-season), they got to the WS in his down first year and it remains to be seen this year. But perhaps the biggest reason Dombrowski overrated him was for his energy, and while I (and most of us) have never been a fan of that thinking (see also, Bell, and now Merrifield) it's hard to argue that he hasn't been important in the clubhouse (and beloved by a big portion of the fan base too, as merely an entertainer, though his entertainment value goes down considerably if he doesn't give Liam any dingers to cheer).
In the end the only downside to the deal (and the mysterious length) is $ that the Middleton-era Phills will probably be able to manage without serious consequences.
There are a few other deals - Lorenzen deal wasn't great but low-cost, reasonable risk, Thor deal was probably fine. I think the Soto trade was still good especially with Clemens being useful.
The Phillies gave up Billy Sullivan for Pache.
And Klentak was still the GM when they did the Mead/Sanchez deal.