....while making hundreds of thousands of dollars and having a job only 30 people in the whole world possess. Part of the reasoning (spitballing here) is that, like you say, he's better suited to a team that's actually rebuilding. He's not an automaton, he's a living, breathing person. If you know this, what makes you think he doesn't? If he didn't think he could find another FO job that granted him the same authority and power, do you think he would have left?
Also, you do remember the existence of Larry Lucchino right? He didn't decide on the purchase of *all* of the groceries before either.