The aim of our paper is to analyze the way the Jews are portrayed in the Dialogi. This piece, traditionally attributed to Gregory the Great, was subject of debate about its true authorship since the early modernity and, especially, from Francis Clark’s work. In order to address this problem, we will carry out a meticulous analysis of the only exemplum in which the actor is a Jew, contrasting the coordinates of this story with the information obtained from the Gregorian Registrum epistularum. As a second step, we will investigate to what extent the image of the Hebrews from the Dialogi matches or not with the one presented in the Gregorian theological works. We consider this procedure will allow us to contribute with a new element to the debate on the Gregorian authorship of the Dialogi, as well as achieve an in-depth look at the issue of the image of the Jews in Gregory’s work.