Urban violence is an emerging challenge to development and democracy across Latin America. How do cities negotiate this challenge alongside pressures to compete in global markets and enable greater political participation? This article analyzes the politics of urban violence in the intriguing case of Medellín, Colombia, which international donors and policy makers herald as having reshaped its urban governance and economic appeal through its response to violence. The article provides a within-case comparative analysis of contrasting outcomes in the trajectories of the political projects Medellín launched in response to urban violence amid the drug wars of the early 1990s and the subsequent urbanization of the Colombian civil war. I argue that a focus on urban political economies and patterns of armed territorial control contributes to our understanding of the politics of urban violence, reveals limitations for the diffusion of the Medellín model, and identifies promising avenues for future research.