Recent years have seen an increase in college and university presidential turnover. Alarmingly, across all 4-year post secondary education institution types, Historically Black Colleges and Universities (HBCUs) have experienced the highest rate of presidential turnover. Between 2010 and 2014, HBCU presidents’ tenures lasted for an average of 3.3 years (Kimbrough, 2017) while the average tenure of presidents across all 4-year higher education institutions in the same years was 7 years (Gagliardi, 2017). Explanations for the high rate of HBCU president turnover include increases in political conflict, internal pressures, external stakeholder demands, and fiscal stress. Despite these explanations, some scholars believe that “scholarship on presidential turnover is lacking cohesion and is in need of a theoretically grounded conceptual framework…” (McNaughtan, 2016, pp. 3-4). This study uses the portraiture method and builds upon a theoretically grounded conceptual framework that includes person-organization fit theory, person-job fit theory, and organizational culture. This study aims to explore how former presidents' perceived fit with their former HBCU employers contributed to their short tenure presidencies.