We can't expect Middleton to tell the new President what the plan should be. We need the aspiring Presidents to tell him what the plan should be, and for him to recognize who the right guy with the right plan is.
To some extent it is still not realistic to go into total rebuild mode, but by having no permanent GM and cutting payroll this season, there's clearly not much of a win-now mandate either.
I doubt Klentak had more than one conversation about that international signing. Sal gets to make those calls, and he reports to Minnitti. Whatever the politics and screw-up was there, they were stuck with it. That does seem like a fireable offense though.
I don't think Klentak's trades were bad just because they cost some talent compared to signing free agents. Nor can you separate them, because even though Arrieta, Robertson and Cutch didn't cost anything but money, they still contributed to the poor payroll management as much as Segura (who was himself only here to help move the Santana contract). These were all bad moves because the players weren't good enough (or in Robertson's case, hurt).
You can't separate any of it really. They profoundly misjudged every player they added in 2019 and 2020 except for JT, they misjudged their ability to sign JT, and they missed on nearly all the young players they thought would help the team win for the last two years (Herrera, Williams, Pivetta, VV who wasn't even inherited). They acted as though they had the $ and the talent pipeline to eat (or at least tolerate underperformance from) the back end of these over-30 guys, and now it turns out they don't.
Klentak accomplished very little, but it's also incredible to look back on the past five years and think that Middleton still wants MacPhail and Gillick to set a new direction, and apparently doesn't own a mirror. It's just business as usual in that sense. Somehow Middleton himself can identify the problem - that except for two outlier periods the Phillies don't consistently produce talent or win - but not sure he has a clue how to fix it.