The Mexican government’s brutal repression of the Student Movement of 1968 in the infamous Massacre of Tlatelolco exposed and exacerbated a serious crisis of political legitimacy. This study examines the cultural impact of this watershed event through historically contextualized readings of five paradigmatic novels: Carlos Fuentes’ La region mas transparente (1958), Fernando del Paso’s Jose Trigo (1966), Maria Luisa Mendoza’s Con El, conmigo, con nosotros tres (1971), Jorge Aguilar Mora’s Si muero lejos de ti (1979), and Hector Aguilar Camin’s Morir en el golfo (1986).