This study expands previous research on stress in the superintendency by addressing the links between the superintendents' levels of stress, early trauma, coping responses, and superintendent health. The study focuses on the intersection of sex and gender in these relationships. A nationwide random sample of superintendents resulted in a working sample of 1,890 respondents who completed an online questionnaire. The survey was constructed based on the findings from previous research on job satisfaction, CEO and educator health, occupational stress, well-being and coping behaviors, and adverse childhood experiences. This topic is particularly relevant to leadership preparation, not only because few programs address health and stress, but also because of the powerful role that good health and resiliency play in successful leadership.