One of the more significant success stories of inclusion in US higher education has been that of Amherst College’s transformation into a highly diverse student body. This research examines the role and effect of presidential leadership in Amherst College’s diversity achievement. Using a case study design, data was collected from interviews with then President Anthony Marx, various members of the College community who were central stakeholders in the diversity initiative, and selected archival original College documents. The research draws on Bolman and Deal’s (2003) organizational leadership framework to analyze how various institutional dimensions of the College were challenged and changed to facilitate greater inclusion of an increasingly diverse student body. The study finds that Amherst College’s successful diversity and inclusion program was largely a function of transformative presidential leadership in significant areas. At the initial level, the president was able to capitalize on the national and global demand for increased access to quality higher education, as well as Amherst College’s founding principle of inclusion, to sell the vision to Amherst College’s stakeholders. Secondly, successful transformative leadership was based on the president’s ability to develop and implement practical and structural mechanisms in areas of management and financing to recruit and ultimately support a more diverse student body. Finally, the research highlights that transformative presidential leadership is also contextual and must be based on both the educational institution and the environment in which it operates.