The introduction of real-world, meaningful tasks in mathematics classrooms promises to create opportunities for enhancing students' learning through active engagement with mathematical ideas; however, researchers have given little consideration to the contexts in which urban high-school students live. The case study of three students reported in this article drew on data from a larger, two-year study of the Students for Social Justice (SjTEM) program in a secondary urban school that examined understanding of graphical data through grasping the trade-offs of urban planning in the students' neighborhoods. The findings indicated that geospatial modeling supported students in understanding graphical interpretations of data, the importance of ecological impacts, and the nature of urban planning.