Effective educational leadership is essential for the success of schools and ultimately student achievement. The impact of school leadership may be even more pronounced in charter schools. Due to current and unprecedented growth, unique design, and complexities of political, financial, and governance issues they face, there is a need for more highly qualified charter school leaders and perhaps even "differently" prepared leaders. In this qualitative study, the authors documented the characteristics and skills of two successful, sustained charter school leaders who retrospectively described their evolved and evolving roles over twenty five years. Each transformed high-poverty, low-performing schools with at-risk populations and led with vision, passion, and a relentless desire to positively influence their organizations and ultimately improve student success in their communities. Although many of their skills and characteristics fall within existing theories, such as situational leadership, transformational leadership, and distributive leadership, they embodied a level of dedication and commitment to the original communities in which they founded charters lasting over a quarter of a century. The findings suggest that founding a charter school and seeing it through to success over time may more closely resemble missionary work than traditional school leadership.