This qualitative case study focuses on a school created to educate expelled students, specifically examining the relationships between educators' beliefs and philosophies and daily school life. At this school, Kelly's ("Last chance high." Yale University Press, New Haven, 1993) competing philosophies of "traditionalism" and "developmentalism" got enacted at the school and classroom levels in ways that precluded effective practice. These competing philosophies reflect broader national and international discourses that simultaneously promote neoliberal marketization and democratic emancipation. Conflicting sub-cultures at the school under study emerged as the most salient conduit at the school level for the enactment of these competing philosophies, and administrators' practices at the school and district levels unintentionally reinforced these conflicting sub-cultures. Findings suggest that improving the educational experiences of persistently disciplined students requires the clarification of philosophical underpinnings and cohesion of policy mandates and implementation at federal, state, and local levels. Without such clarification, alternative schools may serve more to push students further out of school and into the school-to-prison pipeline than to reengage them.