I'm sure this is probably true of most teams, successful or not, but it's funny how similar the Klentak/Dombrowski and Wade/Gillick eras have been in terms of some pretty important core talent acquisition, but then needing a change to truly make it all work. Of course Wade was more about Arbuckle's draft picks while Klentak was about spending Middleton's money (and arguably Dombrowski simply getting him to spend more where MacPhail and Klentak could not is also his biggest plus).
Of the current roster, front office and coaching staff, the following people were originally Klentak acquisitions/signings:
Bryce Harper (2019 FA)
Bryson Stott (drafted 2017)
Alec Bohm (drafted 2018)
JT Realmuto (2019 FA agent)
Johan Rojas (2018 intl)
Logan O'Hoppe (drafted 2018, traded for Marsh)
Zack Wheeler (2020 FA)
Cristopher Sanchez (infamous 2019 trade)
Brian Barber (hired prior to 2020 season)
Rob Thomson (hired prior to 2018)
Sam Fuld (hired 2017)
Obviously the shortcoming of the Klentak era is also highlighted by the fact that they still needed Schwarber, Turner and Castellanos to complete the starting nine and Walker in the rotation when that might have been Ortiz, Kingery, Haseley and (I dunno - Cole Irvin?).
Then you've got the Amaro guys: Nola, Suarez, Seranthony and the since-departed Hoskins. But I feel like ultimately Amaro is a bigger failure than he gets "credit" for. It was easy to caretake the Gillick team and just add great pitching, but his overall organizational era was a disaster, and his position player moves weren't that great either. He had his financial hands tied too of course.