This paper examines the unfinished “dialogue” between Cavafy and Aristophanes that takes place in the poet’s early fragmentary and untitled prose text on the Sophists, part of his broader discussion of the relationship between the Sophists and ancient theatre. In undertaking the defense of the fifth-century Sophists Cavafy adopts the views of Grote, according to whom their condemnation by contemporary and later authors was prejudiced and therefore unjust; the passages from Grote on which the poet probably bases his disagreement with Aristophanes’ negative view of the Sophists are given. While Cavafy criticizes the references made in the Clouds to the moral corruption of youth by the Sophists, the paper concludes that his intention is not so much the contradiction of Aristophanes as the rehabilitation of the Sophists, as the comic poet becomes the “vehicle” for displaying the widespread prejudice against them. It also suggests that Cavafy’s agreement with Grote reflects a broader ideological convergence with the historian’s views.