Many adolescent learners have difficulty understanding the relevance of mathematics for their lives. This problem is particularly pernicious among Black and Latino adolescents who often face cultural stigma that can affect their perceived value of mathematics. The present study used concurrent nested mixed methods to explore this issue in 419 urban Black and Latino adolescents. Structured classroom observations, a computerized cognitive assessment, and surveys were used to examine how teacher math applications (TMAs) and adolescent cognitive flexibility interact to predict students’ valuing of mathematics. From a subset of the larger sample (n = 37), semistructured qualitative interviews were used to understand how these adolescents came to view mathematics as a transformative tool in their lives, particularly in the face of cultural stigma. The quantitative results revealed that TMAs were associated with students’ value of mathematics. However, these results also illustrated how TMAs interacted with adolescent cognitive flexibility to predict students’ growth in valuing mathematics over the school year. The qualitative interviews corroborated the quantitative findings, but also revealed 3 themes that extended the quantitative results, uncovering racialized facets of valuing mathematics. The 3 themes that emerged were: utility orientations, alternative messengers, and resisting stigma and protecting collective identity. Altogether, these results demonstrated the role real-world applications, race, and adolescent cognition can have in urban mathematics classrooms. These findings suggest teachers’ sensitivity to these issues can support Black and Latino adolescents’ persistence in mathematics and understanding of self.