The study illustrates the leadership role in an academic organization and investigates the leadership approaches that might account for an organization’s success. Leadership at Harvard University is studied as a case study to characterize leadership legacy and to explore whether or not a combination of three leadership factors might be indispensable to the success of academic organization. This study is conducted through a thematic design. Short quotes are reviewed to provide a practical analysis of the combination of three leadership factors that are associated with long-term leadership (20 years or more) in comparison to medium and short-term leadership (fewer than 20 years). Qualitative data is obtained from secondary sources such as published documents, university biographies, and relevant literature. Results from this study suggest that the success of an organization is conditional on the existence of a three-factor model of leadership (visionary, transformational, and learning leadership). The study also shows that a three-factor model has been more useful in long and medium-periods of leadership when leaders have implemented changes and have transformed the organization, in comparison with shorter periods of leadership. Further research should be conducted to examine the effect of other leadership approaches and to explore the idea of inappropriate laissez-faire leadership in academic organizations.