This study is an almost biographical work analyzing the process of academic leadership development in a single individual. It focuses on a 29-year period of professional activity, although there is contextual information on earlier periods in the subject's life. There is a wealth of information on the community college as a singular type of higher education institution, including its developmental chronology, its unique characteristics, components, constituencies and operational complexities. The concept of academic leadership is analyzed in the Frames Theory context of Bolman and Deal (1984, 1997, 2003). Frames theory is connected to cultural, organizational and learning theories to firmly establish the capacity of individuals to adapt to different environments and adopt behavioral characteristics reflecting the contextual frontiers of that environment. Successful academic leadership is determined by individual capacity to understand the complex and dynamic characteristics of different personalities within the different environments of the higher education institution, simultaneously orchestrating and navigating that variety in the pursuit of stated institutional goals.