This qualitative dissertation study focuses on the effects of neoliberal school reforms and their effects on a charter school in an historically dispossessed Chicago community. The author situates the school’s micro-level culture within larger macro-level, exo-level, and meso-level contexts to explore the interactivity between nested, ecological systems. The author argues that historical dispossession is an institutional trauma that is the result of unhealthy systems and neoliberal circuits of worth that result in undue accumulation for some and systemic/institutional dispossession for others. The study serves as an object of reflection for exploring the efficacy of neoliberal school reforms and provides empirical evidence, a philosophical reflection, and pedagogical implications based on the school’s “predestined failure” and the school’s resulting “story of dispossession.” Student, families, the community, and educators all experienced varying levels of dispossession based upon a myriad of converging neoliberal logics that had created a field of possibilities for educators who intended to provide a high-quality educational choice in the form of a charter school founded through philanthrocapitalist financial funding and a corporatized process for gaining charter school approval in the city of Chicago. Utilizing Critical Race Theory, post-structuralism, grounded theory, and the concept of neoliberal circuits of worth, the author traces neoliberal logics from macro- to micro- systems. The author argues that institutional systems that exacerbate historical dispossession within new generations creates compounded deprivation and systemic/institutional trauma that is transmitted to those who are repeatedly dispossessed by the public institutions that are purported to provide them with equal and equitable educational opportunities. The need for healthy public systems and implications for moving forward both within school settings and within the field of educational research are explored.