Teaching writing to students of high need in an urban school is simultaneously pedagogical, curricular, and political. Students labeled "at-risk" for school failure often have lowered expectations placed upon them from without that impact how they feel within. Compounding this problem of perception is the real issue of heightened surveillance on these students, including the disturbing trend of involving the police when students break the rules of the school; in addition, their own history of juvenile incarceration often exacerbates their school failure. This article addresses these issues in an urban context, as well as provides insight into literacy teaching that assists students in the acquisition of knowledge, literacy, and expression.