This essay explores the assumption that the sense of perplexity and surprise that characterizes the reading of many of Borges’s works of fiction is related to these stories’ direct and explicit exposition of transitive thoughts transcending caesurae (Bion, 1977). Borges presents a world in which diverse and even contradictory points of view or interpretations coexist. These texts allow for paradox to be acknowledged and to remain unresolved. The author suggests that Borges’s writing style, the form of his stories and essays, allows for the containment of the anxiety that the possibility of evolutionary change may create. Borges’s works of fiction symbolize the paradoxical nature of the caesura: inner continuity where there appears to be a break After reviewing Bion’s concepts of caesura and transcendence of caesura, the stylistic devices that Borges uses in relation to the coexistence of different perspectives or interpretations will be discussed. A psychoanalytical reading of Borges’s Theme of the Traitor and the Hero and The South enriches the understanding of processes of failure and success in transcending caesurae. The relevance of the transcendence of the caesura for analytic listening is underscored.