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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. This study uses concurrent nested mixed methods, including structured classroom observations, a computerized cognitive assessment, and surveys, to explore this issue in 419 urban Black and Latino adolescents. The quantitative results revealed that teachers' math applications were associated with students’ value of mathematics and interacted with adolescent cognitive flexibility to predict students’ growth in valuing mathematics over the school year. Semistructured qualitative interviews among a subset of students (n=37) corroborated the quantitative findings, but also revealed three themes that extended the quantitative results, uncovering racialized facets of valuing mathematics: 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.