This article examines how school superintendents and parents in high-needs rural districts conceptualized educational quality. Specifically, this comparative case study of two rural school superintendents presents a contextualized understanding of rural superintendents' and other educators' mainstream views of educational quality, parents and other rural community members' place-based views, and the tensions among these. Primary data sources featured interviews with two superintendents and their constituents, including Board of Education members, principals, teachers, parents, and community members. Findings indicated that both superintendents worked to create an aspirational culture in which education was the way out of poverty for their students, aspirations that were frequently at tension with community values. This article concludes with a proposed critical leadership and pedagogy of place that may help superintendents navigate these tensions.