This article uses a critical sociohistorical lens to discuss and explain examples of the ways in which young people reflect, refract, and contribute to discourses of gentrification, displacement, and racial, ethnic, and geographic community identity building in a rapidly changing urban neighborhood. The article explores examples from open-ended dialogic conversations in one seventh-grade classroom. In their conversations, youth imagine themselves and their communities as sociohistorically yet dynamically situated. We argue that such spaces allow for schools and students to bridge in and out of school worlds, amplifying young people’s relationships to enduring struggles in changing urban contexts.