This chapter addresses the evolution of the crime fiction genre in Latin America by examining the relationship between three of the continent’s major cities and three historical moments. The following case studies chosen are: Buenos Aires in the stories of Seis problemas para Don Isidro Parodi (Six Problems for Don Isidro Parodi, 1942) by Jorge Luis Borges and Adolfo Bioy Casares; Havana in Armando Cristóbal Pérez’s novel La ronda de los rubies (The Ring of Rubies, 1973); and Mexico City in Días de combate (Days of Combat, 1976) by Paco Ignacio Taibo II. The chapter traces a textual trajectory from Borges and Bioy’s parodic games with the English models of mystery fiction to Taibo’s scathing national questioning of the Mexican neo-crime fiction, passing through Cristóbal’s politically committed and Cuban revolutionary crime fiction. That trajectory demonstrates the flexibility of the crime fiction genre, which has allowed it to branch out and adapt to the literary needs of different authors and contexts in the period between 1930 and 1980 in Latin American literature.