The present paper is an analysis of topics related to discourse and imagery as articulated in Héctor Bujanda’s novel La última vez (2007). Critics broadly regard this work as a modern archetype for a sort of literature that employs apposite sets of images and establishes relevant metaphoric spaces as underpinnings for a historical frame of reference. In the case of this novel, that frame of reference is the wave of unrest known as the Caracazo (1989). Strictly speaking, the work’s discursive register displays traits and context that revolve around those protests and their aftermath. Due to the manifest political character of the novel’s context, it will be necessary to evaluate the characters’ idiosyncratic verbalisation of their experiences as emblems of the author’s political identity. The article’s analytical direction, therefore, is intended initially to identify descriptive patterns that demonstrate the author’s political proclivities, starting with the way the city of Caracas is represented as a den of persistent crime, culminating in the events that led to the coup d’état of 1992. It then proposes a reading strategy that should enable critical insight into the demonstrable features of 1990’s Venezuelan society. In particular, such insights will shed light on particular contemporary issues linked to Chavismo and its methods of governance. Lastly, and in view of this particular novel, I aim to explain the set of aesthetic and ideological tendencies that characterise XXI century Venezuelan narrative and political rhetoric.