In 1970 Herbert Simon was invited by the Sociedad Argentina de Organización Industrial to deliver lectures on “Business Management in the Technological Era.” He asked for an audience with Jorge Luis Borges, the director of the Argentine National Library. Simon had read Borges’s stories and was particularly fascinated by “La Biblioteca de Babel” (The library of Babel), wherein he discovered that Borges, like him, conceived of life as a search through a labyrinth. The Spanish translation of the interview was published in Primera Plana, an Argentine journal. The brief interview sheds light on some of Simon’s ideas about determinism and free will. His critique on maximizing rationality and his suggested approach to decision making have contributed to enlarge the concept of rationality as construed by standard economic theory. Consequently, it may be argued that Simon is incorporating free will in economics. However, though Simon’s position implies an advancement for the role of free will, the whole context of his ideas conditioned it, thus resulting in a “weak” notion of it. During the course of his conversation with Borges, Simon clarified his personal stance, which is consistent with his ideas. The paper will reveal Borges´s and Simon’s understanding of free will. This paper also contains part of the conversation between Simon and Borges that has not been published previously in English. Introducing it in its entirety is a contribution to the knowledge on Borges’s and Simon’s thought.