This article explores the ways in which social studies classrooms can explore the history and status of U.S. territories as "unincorporated." We focus on the "Insular Cases" and in particular "Downes v. Bidwell" (1901), examine the construct of colonies as anathema to democracy, and explore the precedents court case rationale for the existence of unincorporated territories. Finally, we address the essential questions raised by this case that can be incorporated into lessons and units and suggest instructional suggestions and pathways for addressing the problematic past and present of unincorporated territories.