An interesting thought experiment, especially in how you framed it.
Why would it have to be an "administrator?"
What about a parent? Unlike public schools, private schools actually have to listen to parents' concerns about trifling things like student safety.
If I knew some teacher's violently crazy ex might be showing up at my kids' school, you can bet your house the "administrators" would be hearing about it, from me. And that $5K gift to the Annual Fund gets at least an hour of one-to-one facetime with the Headmaster.
Too bad for the public school suckers whose kids are bullied to death and whatnot.
To keep the analogy close to the original story.