School leaders are under pressure to produce not only academic results but quality athletic and extracurricular programs. The most well recognized and publicized athletic program for high schools in Georgia is football. The football program is often the way in which citizens in the community identify and engage with the school and its stakeholders. This qualitative descriptive case study used interviews, observations, program literature, and historical documents to profile two of the winningest active head high school football coaches in Georgia. The coaches in this study are active head high school football coaches in Georgia with over 200 wins in their careers. The head coach participants in the study are Alan Chadwick, currently the head football coach at The Marist School, and Rich McWhorter, currently the head coach at Charlton County High School. This study adds to the body of knowledge on head high school football coaches as institutional leaders at their schools. Although the two coaches were in very different settings, this work discovered some common themes in both coach’s leadership styles. This dissertation also attempted to make a correlation to Kouzes and Posner’s (2007) Five Practices of Exemplary Leadership from their book, The Leadership Challenge. These two successful head coaches model the behavior they expect of those in their organization with their work ethic and dedication, build a sense of community and esprit de corps on their teams, and rely on intensive off-season and in-season conditioning and weightlifting programs.