This dissertation examines the political economy and economics of the school-to- prison pipeline (STPP). In my first essay, I interrogate approaches to the economics of the STPP. I then situate my analysis within the theoretical lens of Robinson (2000)’s racial capitalism, to show a political economy approach for understanding the nexus of public schooling and the carceral state. Building on the concept of enclosure as presented by Sojoyner (2013, 2016), I describe the emergence and impacts of the STPP to show how this dynamic functions as a racialized economic enclosure, through punitive discipline, exclusion, and criminalization. Next, I examine the relationship between carceral school environments and stu- dents’ expectations of their future educational attainment. Using the National Crime Victimization Survey: School Crime Supplements 2005-2015, I show that visible and intrusive security measures- especially metal detectors- negatively impact students’ expectations of their future educational attainment, and for Black and Hispanic or Latinx students the effects tend to be larger. I interpret these results as evidence of the ways in which carceral schools work to enclose opportunity away from stu- dents, using a conceptual framework including Shedd (2015)’s notion of perceptions of injustice. My final essay examines the role of school discipline in college-going decisions and outcomes.. This study uses the High School Longitudinal Survey of 2009 to show how experiencing suspension impacts students’ decisions to apply to college, and admissions and enrollment outcomes, finding evidence of a negative impact of high school suspensions on a student’s decision to apply to college. Similar to labor markets and criminal records, these findings provide evidence that school discipline, when acting as a negative credential, may potentially work to enclose and limit options and pathways for post secondary education. In the enclosure framework, I demonstrate these two particular instances of how schools oriented towards punitive discipline and criminalization limit education and economic opportunities thus perpetuating and compounding inequality by race, ethnicity, gender, class, and other dimensions. Ameliorating these issues requires a broad and radical approach towards transforming schools, and the economy, as sites of economic liberation rather than discipline and criminalization.