Although much scholarship on community-engaged pedagogies attends to student negotiations of difference, little attention has been paid to how instructors navigate difference, particularly racial difference, across classroom and community spaces. In this article, we use the concept of brokering to examine how seven different instructors of a community-engaged writing course titled “The Literacy Narratives of Black Columbus” imagined the racialized spaces of the course and facilitated engagement between students and community members in those spaces. Drawing primarily on instructor interviews, we present three approaches instructors took to imagine and facilitate student and community engagement across racialized and spatialized boundaries. We found that instructor positionality influenced how they imagined and negotiated the roles of brokers who could facilitate connections between students and community members as well as provide students with cultural knowledge necessary for navigating the course’s racialized spaces. Ultimately, we argue that instructors, particularly in predominantly white institutions, must carefully consider race, space, place, and their own positionalities when planning and implementing community-engaged pedagogies.