I mean, Boras might have been annoyed they didn't sign Keuchel though I thought the whole "Keuchel calls out Philly" headline was way overblown. Right now Boras should be grateful we took both Arrieta and Harper. Maybe he'll bring us Moose next year.
As for Harper, of course he wants to win and improve the team always (and players aren't known for being long-term thinkers) but he's going to be here for a long time, it wouldn't be great for him if the Phillies had traded away Haseley and Howard just to upgrade the rotation and bullpen short-term.
Boston, despite their four titles, always seems to be dysfunctional. It went bad for Theor too. Dombrowski supposedly expected Cherington to be his GM when he got hired too. And the he lost the next guy to Arizona. I agree he's Gillick-like, in Detroit he just had the advantage of an owner who always thought short-term.