In this article, the author argues that the persistent underachievement of many African American male students in urban school districts requires pedagogical interventions designed to re-engage and re-orient students to mathematics as critical cultural activity. While counterstory, a critical race theory construct, has wide application across educational research, few researchers have explored its relevance for urban mathematics education. Here, the author provides a grounded operationalization of counterstory by examining the pedagogy embedded in African American narrative on literacy. Using data from a participatory action research project involving male African Americans in South Los Angeles, the author then demonstrates how counterstory is embedded in the mathematical activity associated with graphical representation and trend analysis of data. Through the theorized approach to counterstory presented, the author provides useful direction for education researchers interested in counterstory, and for mathematics educators attempting to broaden their pedagogical approaches to teaching and learning mathematics.