But, so, alas was Klentak (helped greatly by RAJ and Gillick's hires). All of that is really on MacPhail though (and Middleton doesn't get a pass).
I wonder who would be running the team right now if there had not been a pandemic and the prospects for Nashville's expansion team had seemed more promising.
Regarding Schwarber, I'm sure he's at peace with being a DH - some other players might be annoyed to get signed to play LF and then moved two days later. But Castellanos is also a godawful RF who's only played 20 career games in LF (though he used to stand on that side of the field when he was a bad 3B).
Regarding dollars per WAR, nobody actually pays that. Sometimes it's more, sometimes it's less. Would be nice to have a system that wasn't artificially depressed on the one hand and inflated by equally artificial market forces on the other, but so it is.
Plus you're not just paying for production, you are paying for entertainment and ticket sales. The Phillies were a pretty unappealing product - no goodwill left from the Bryce signing between the pandemic and the lack of playoffs - and now, not so much because these two players are STARS but simply because Middleton finally lived up to the expectation Jimmy Rollins set for him 10 years ago ("Steinbrenner South"), there's bound to be a little more excitement. If it works.
Of course, the Braves and Mets also forced the Phillies' hand. Last year it looked like they were competing to win a weak division, and in fact they were, but that didn't matter after the deadline and in the playoffs. Add in Cohen's checkbook and having a Top 5 payroll isn't enough anymore.