I enjoy your posts Cello but you are way off base on this one.  I am a teacher and you missed the real story.  It has nothing to do with a foundation and lots to do with Democratic insider politics and shibai.  They just got caught this time. 
If the Waipahu HS principal wants to apply, let him go through the public process like anyone else.  If he really has substantial and documented success running a large school system, let him say so and compete with all those who do have such expereince.