Background/Context: For over three decades, Jean Anyon produced scholarship that revealed the deep-structural causes of educational inequality. Anyon’s work in political economy includes a racial analytic; she argues that access to education does not reduce economic disparities in urban communities of color, and that schools in poor and working-class communities of color in particular often serve to reproduce inequality across generations. It is common, however, for critical scholars analyzing educational inequality to be steeped in either Marxism or critical race theory, and less knowledgeable about the other. As a result, analyses rarely place equal emphasis on both theoretical frames or synthesize race and class. Using theories of racial capitalism to extend Anyon’s political economic analysis, we contend, brings forward conceptual tools and angles that capture the material and ideological work being done by current, highly racialized neoliberal restructuring in and beyond the school walls. Purpose/Objective/Research Question/Focus of Study: We focus on the ways race operates as a material force that is part and parcel of the capitalist dynamics that create and require inequality, and argue that racial violence structures capitalist development, making the systematic impoverishment of urban schools and neighborhoods possible and permissible. First, we provide an overview of two key theories of racial capitalism from Cedric Robinson and Jodi Melamed. We then revisit Anyon’s work on school knowledge and the hidden curriculum to consider how these operate as forms of epistemic and psychic racial violence that (re)produce racial capitalist conditions. Next, we consider Anyon’s work on political economy and public policy in light of the ways neoliberal racial capitalism links the production of differential human value to capitalist development in urban neighborhoods, deploying public policies that limit the life chances of working class and poor youth of color. Finally, we consider the implications of these dynamics for the “radical possibilities” that inhere in urban schools, arguing that opposition to racial capitalism stretches Anyon’s formulation of the “radical” and the “possible,” as youth oppose racial capitalism by resisting the school itself. Research Design: In this theoretical article, we use theories of racial capitalism to analyze Anyon’s major works in urban education. Putting core concepts from these theories into conversation with Anyon’s findings and her own theorizations, we offer an analytical synthesis that braids together race and class to unpack the production of urban educational inequality. Conclusions/Recommendations: We propose that reading racial capitalism into Anyon’s work can extend her political economic analysis, and through such extension, her findings, analyses, and arguments can be leveraged to help us better understand how race and racism interlock with the ideologies, social structures, and chaos of capitalist development and neoliberal reform. We contend that such an analysis can build out both the “radical” and the “possible” with implications for how we think about opposition and organizing not just within but against schools.