A leadership emergency is developing in higher education. According the American Association for Community Colleges, by 2022, 75% of current community college presidents intend to retire, and within five years an additional 15% will exit the presidency. As these individuals leave their leadership role, the higher education environment they leave behind will change. Understanding this impending leadership crisis, the purpose of this qualitative interview study was to describe and understand the leadership experience of former Florida College System institution presidents, their perspective and reflection on the institution of the presidency and its evolution, and their thoughts regarding the pertinent challenges facing current and future presidents in the next three to five years. Data were collected through explorative interviews with six former Florida community college presidents. Thirteen themes emerged from the analysis of the data. These themes aligned with and expanded the understanding of the community college presidential leadership experience. Important research implications for academic researchers and practitioners were discovered and additional lines of inquiry for further research in the areas of presidential leadership experience emerged.