Any fan or writer as old as, or really half my age, grew up in an environment when the Phillies were always hard up for cash. The Carpenters had a main-line view of how much the players should be played and were very upset at the rising salaries. They sold to a management group they appointed Bill Giles, he of little $, to assemble and serve as managing partner, in large measure because they knew they could count on him to join the Commissioner in opposing greater player salaries, signing bonuses, and rights generally. Ruly Carpenter strongly supported the farm, but still seemed to view the players as the modern equivalent of serfs. Giles needed his draw from the team to live the life he wanted so, in addition to stripping the farm system, he had a very tight budget. The budget situation has drastically changed but the memory of good players jettisoned and good draft picks avoided to save $ made an indelible impression, as did the whiteness of the Giles era Phillies minor league system.
DD has been spectacularly bad at signing supporting players to support his stars and has yet to make the farm productive. He has proven the consensus take on his performance that he could push a team to (almost) the top but would leave it troubled. He seems to still not be the guy to build and maintain a sustained winner.