This essay deals with the notion of retranslating the literary work from a double perspective: first, some theoretical principles are established (Pym 1998 and Venuti 2004/2012), where we can find why retranslations of classical works are so often published; secondly, in order to illustrate those principles, we examine the historical journey of Poe’s retranslations in Spain, from the first story published (1858) up to the present; finally, so as to understand further both the theoretical principles and the retranslations of the author’s work, we examine different aspects of three retranslations of Poe’s “The Business Man” (1840): Julio Gómez de la Serna’s (1951), Julio Cortázar’s (1956/1970), and the one by the autor of this article (2008). The analysis of some distinguishing aspects of those three translations allows to highlight the important role played by retranslation in the canonization of authors in the intended various target systems.