Research stresses a need for more contextually nuanced urban teacher preparation programs that explore racially oppressive structures in society. This article presents a case study of five aspiring teachers who participated as mentors in a 2-year program for ninth grade students at Riverview Academy, an urban school. This study uses the opportunity gap explanatory framework to analyze if and how, through this program's preparation protocol, these five aspiring teachers learned to build on rich community based knowledge, while problematizing the various social, political, and economic conditions that contribute to racial inequity. Participants' individual shifts varied, but, the group came to collectively "see" and name three consistent issues. Unfortunately, they were unable to formulate broader critiques of the "unseen" racialized macro-systems underpinning the micro-issues they saw. This study raises important questions and implications that speak to the ways in which racist macro-structures shape and are shaped by micro-level behaviors, beliefs, perceptions and outcomes, particularly in the context of preparing future teachers for work in urban settings.