This case study examines the perspectives of a teacher and a set of students in a U.S. history classroom in a "last chance" public New York City high school--with "last chance" being a common term used to describe schools designed for struggling students, those who have a history of truancy, or those who have dropped out. The research question is as follows: How does a skilled teacher engage marginalized students through law-related education in a U.S. history course? Here, this study documents one skilled teacher and his law-related education pedagogy. Specifically, it focuses on how he engaged marginalized urban students by means of emphasizing an open classroom environment, democratic living skills and community building, and thorough disciplinary knowledge and skills. This study furthers our understanding of the ways in which urban students can be better prepared for engaged democratic citizenship in a multicultural democratic United States.