In this article, I offer a retrospective case study about my early, short-term work within the U.S. Office of the Assistant Secretary for Health and then my later, longer-term work within the U.S. Centers for Disease Control and Prevention, where I endeavored for two decades largely to help our nation’s schools improve health and associated education outcomes. First, for context, I briefly portray the nature of our related political and public health systems. I then frame this retrospective by illustrating how my serial employment within other public health system organizations led to, and then resulted from, my work within these two federal public health agencies. To represent the many talented individuals in each organization with whom I had the good fortune to work, I name only one in each organization. I then characterize how these individuals and organizations progressively shaped my work and career. I conclude by speculating about prospects for academic institutions to more purposefully prepare students and faculty to work within federal government public health agencies.