The purpose of this study was to examine the practices of teachers in designated failing segregated urban setting. Many students in poor urban settings live in generational poverty and do not have visible role models to emulate. Most are overexposed to a Hip-Hop philosophy that supports misogyny, over-sexualized masculinity, and violence. There is a gap in the research on teachers' perspectives from this setting and how their practices are actualized in the classroom. This qualitative study used semi-structured interviews, observations, post-observation interviews, and document analysis of five teachers working in a southeastern segregated middle school. The teachers told tales reflecting times when their values conflicted with that of the school and how they learned to maneuver around them. Culturally Relevant Pedagogy was utilized as a framework to analyze the practices of teachers. Teachers in this setting bartered with their students and cashed in on students' cultural capital in strategic ways. This allowed them to teach them content while also engaging them in discussions about critiquing problems and strengths associated with Hip-Hop music and culture. Although teachers did not verbalize it, they were able to delicately integrate art via Hip-Hop culture into their curriculum, and support the overall goal of the school while focusing on needed standards. Educators need to prioritize the needs of students above policies and mandates for educators in urban settings. The needs of the students are paramount in these settings. The academic needs must be met, but we must also understand that there are ways to honor students' cultural assets.