To be sure, big-city school superintendents are paid handsomely. In 2014, the salaries of superintendents at cities that are part of the Council for the Great City Schools ranged from $99,000 to $339,000, in addition to platinum health care, pensions, life insurance and other related benefits. Most superintendents of the biggest school districts clear $300,000 easily, with the job of helming New York City schools drawing upward of $500,000.

“Anybody who gets into this knows full well that the demands are extremely high,” Casserly says. “The context in which you do this job now is probably more difficult now than it’s ever been. It does give some people pause.”