Using methods of naturalistic inquiry, this study examines preservice teachers' conflict with classroom management strategies used in a predominantly African-American urban elementary school. It highlights the theory/practice dilemma, focusing on the tensions between the democratic strategies taught in university classes and the more authoritarian strategies actually found in the urban classrooms. The use of power and caring, evident in the interactions of the teachers with their students, was seen as a way to make sense of these strategies. The African-American and European-American researchers, both university faculty, share their differing perspectives, insights, and questions as they tried to make sense of their students' experiences, especially how subtle forms of racism and strong cultural norms impact one's teaching. (Contains 1 footnote.)