Recent studies reveal that a considerable number of U.S. community college leaders will be retiring in the next several years. The concern is that with the large turnover, history, culture, and important lessons of leadership will be lost. The current research on the lives of presidents, their career paths, and experiences in community college leadership centers on approaches to the study of leadership at the macro level. Limited research exists in the published literature that reports and analyzes the development of individuals as community college leaders at the micro level. This results in a gap regarding understanding leadership development and strategies to prepare leaders. This study addresses this gap by providing a critical description of the leadership development of one individual who became a community college chancellor and who the literature on the community context indicates contributed to the local and national context for community colleges. Biography is gaining prominence as a legitimate and viable tool in the study of leadership. Few biographical studies currently exist which focus on leadership development in context at the micro level. This dissertation is a biographical, qualitative study of the leadership path and legacy of R. Jan LeCroy, a community college leader. The study combined two viable approaches to biographical inquiry: a scholarly chronicle and the realist approach. Data included the use of primary and secondary sources and included interviews, document analysis, and archival data such as newspaper articles, memos, and minutes of meetings. The data were analyzed and the findings discussed using the theoretical framework of Gronn's (1993) career model of leadership, Vaughan's (1986) study of the career paths of presidents, and Sullivan's (2001) study of four distinct generations of community college leaders. The leadership path of R. Jan LeCroy paralleled the four stages in Gronn's (1993) career model of leadership; he shared characteristics of the presidents surveyed in Vaughan's (1986) study; and he fit the profile of the second generation of community college leaders as described by Sullivan (2001).