That is a complicated one. On one side the owner of a privately-owned boarding school doesn't have much to worry about in terms of accountabilty and can fire people with little to no care, what to say of an employee attempting blackmail. That said, a privately-owned one is dependent on its image and patrons, have to account more for how conservative values of theirs might hit the school's venues, so more vulnerable to such a exposure.
But considering it would backfire into the school as a whole, not really advisable at all as a move from someone working at the school (at least without reason to believe one might take the owner's place as principal and "save" it)....