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Multicultural education scholars advocate the teacher’s use of empathy to build strategic relationships, develop partnerships with parents, and to frame professionally informed perspectives of students, their communities, and their cultural background. This paper explores the value Black male students place on their White female teacher’s ability to empathize with them for the purposes of advocacy and improvement of the teacher’s cultural responsiveness. Paper uses data from a mixed-methods case study including 2 White female teachers teaching in a large, urban school district and a cohort of their Black male students. Findings have implications for the professional preparation and development of teachers interested in student advocacy and community building. Also, the paper delineates the challenges and tensions associated with this work.