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Rural communities in the south are shaped by a legacy of racial oppression carried out through educational systems. In this qualitative, revelatory case study, we examine the experiences of rural, southern school leaders who are tasked with ensuring educational equality. Using critical place-based leadership theory and social capital theory, we surface social constructions of belonging in the community and identify implications for educational leaders. We find the community maintains tight-knit bonding capital that is routed in land-ownership and racial exclusion, which is conceptualized as “southerness.” Administrators who develop bridging capital were best positioned to shift community perceptions for educational equality. The study has implications for research, policy, and practice.