I'm not saying Middleton's money is bad. I just think it's bad when the owner gets too hands-on. And since he's guy who hired MacPhail and MacPhail hired his protege, that's on Middleton too. As an owner, Middleton's main accomplishments are two palace coups that didn't happen until rock bottom (or, in Monty's case, terminal illness) and writing a few checks.
It's pure hindsight obviously but if the 2019 team had stayed in more of a rebuilding mode (while still signing Harper, certainly) we'd had more young players, fewer injured players, the same record or better and a brighter future.
All three of these guys (and Gillick too) said we were gonna experience a Cubs/Astros-like rebuild. The losing, and the low-spending and "second-tier," was supposed to be on purpose. But the talent wasn't there, and Klentak didn't do anything to speed that up in his first couple of drafts. So they spent, and traded. The glacial pace of complete organizational change was also clearly part of the plan (and if it wasn't MacPhail should have done something about it already).
Ironically, we kind of are where the Phillies were with Wade. He got fired even though those teams were winning 'cause they couldn't get over the top and the fan base couldn't stand him. If they did change GMs, especially if it was someone like Dombrowski, I think history would repeat - maybe we get some short-term success with what's already here, and spend money to prolong that, but there won't be anything sustainable.
Klentak doesn't get a good grade overall, no. The question is how long was he supposed to have to meet his goals? If it wasn't supposed to be a long process they probably shouldn't have hired a rookie GM, a rookie coach. Or a President whose career highlight was in the '90s.