I think the players who 'know how to win', because they have played on championship teams is one of the biggest and costliest of baseball myths.
I think Klentak more responsible than Kapler for the woes of the two prior seasons, but think you need to look higher up the organization for the root of the problem.
The Phillies organization, in many most important ways hasn't changed since the Ruly Carpenter teams came up short and he sold out to Giles.
The Phillies as an organization has always been way too much into the old boys network and supporting the Commissioner. They basically see themselves in perpetual warfare with the players. Ruly did a great job driving the rebirth of the farm system and that led to some top talent and enjoyable seasons. But... he sold because he was aghast at the growing power of the players and rued the impact of rising salaries and free agency. He quit largely because he was a classist rich guy who couldn't see his ballplayers as sufficiently worthy of respect and a fair share of the games revenue. It is really quite stark that he sold to Bill Giles, a member of one of the baseball insider royal families, but a guy without two nickles, who had to assemble an awkward ownership team. He was chosen because he was expected to fight the good fight against player salaries and be a supporter of the Commissioner and the old boys. Ruly felt so strongly about these matters that he sold the team to Giles and his partners, creating a severe $ shortage, that resulted in the destruction of Ruly's beloved farm and Dominican Republic operations and the totally over his head Giles serving as his own GM.
Middleton talks a different game, but his hiring of MacPhail is of a piece with Ruly's sale of the team to Giles. MacPhail is again the younger generation of baseball boys club royalty. Despite his talk of modernity and change, Middleton seemed to need this security blanket and badge of loyalty to the Commissioner and the good fight.
In addition to their history of racism (nasty opposition to J. Robinson, failure to sign Negro League stars, failure to sign Japanese or Cuban stars, running Dick Allen and Abreu out of town after demonizing them with racial sterotypes and general assininity like making a federal case of Allen wanting to be called Dick -- can one imagine the Phillies hiring) the Phillies have a long history of not liking their players and blaming them, especially the stars, a black or Hispanic manager, GM, or team President?) for the owners' inability/unwillingness to either pony up sufficient $ to win or willingness to bend (or even skirt as so many winning teams have done) the rules to gain a competitive advantage. Most of those rules have built-in loopholes or are not binding, but the Phillies followed what they interpreted as the intent and the Commissioner's gut wishes for decades -- giving us the self-chosen 'for the good of baseball' battle to the death with Boras over JD Drew, our failure to bust voluntary draft slots, our never busting international cap, our never exceeding lux cap. The Phillies inability to win was blamed on Dick Allen, who was run out of town, on Schilling, on Rolen, on Abreu -- all stars and guys who should have been touted by Phillies and their announcers.
The Phillies front-office ineptitude actually worked against the cause they so strongly believed in: our attitude and racism were so bad that Curt Flood refused to report; it was notes taken by Giles of an owners' meeting that killed the owners in a major showdown with Players Association; it was Bill Giles involvement in the Drew mess which gilded Boras's reputation and made ownership look small.
So, the problem rests in the Phillies organizational culture, probably in the wealthy mainline culture, and sits at the doorstep of MacPhail and probably also Middleton.
Zambonir: Didi has been ok to good, but was a sop to Girardi. Perhaps a requirement for him becoming manager. He wasn't allowed to pick his staff, to the extent expected for such an established manager.