Research in social studies education has raised significant practical and epistemological concerns with the history textbooks used in urban schools. While these concerns are well documented, we know less about their implications for Black students' understandings and applications of historical content. This qualitative, ethnographic study explored six Black, urban students' perspectives on history textbooks and how these textbooks influenced their historical knowledge about civil rights leaders. Guided by the critical race framework, connections are drawn between participants' recollections of textbook accounts and their understandings of contemporary racial relationships and civil rights struggle. Findings suggest a "contentious relationship" with the information presented in textbooks and the need to rethink social studies curriculum and pedagogy in relation to the contextual realities and lived experiences of Black urban youth.