In this paper we present a cross-case analysis of principal leadership in three high-poverty middle schools in South Carolina. This study was conducted under the auspices of the International Successful School Principals’ Project (ISSPP) (Day & Leithwood, 2007; Jacobson & Day, 2007; Ylimaki & Jacobson, 2011). Consistent with other US-based ISSPP teams (e.g. Jacobson, Johnson, Ylimaki, & Giles, 2005), our research centered on principals whose high-poverty schools have realized demonstrative improvements in academic achievement under their tenure. We employed a mixed-methods approach to select the three principals. Next, using interview protocols, questionnaires and analysis frameworks developed by the ISSPP (Day, 2010), our team adopted a multi-perspective approach to identify the particular leadership practices and beliefs which led to increased student achievement and reduced the achievement gaps in these schools. Our findings highlight the leadership practices and beliefs that influenced student achievement and reduced achievement gaps in these diverse, high-poverty, rural schools. Our discussions explore the relationship between the principals’ values and leadership practices and their unique school contexts. We conclude our paper with implications for practice and further research