In Rabbinic literature, Esau (hence Edom), Jacob’s brother, is the character systematically chosen to incarnate the role of Rome, the “wicked empire,” both in the pagan (pre-Constantinian) and Christian periods. With this in mind, this article deals with the imagery of Edom in the classical Jewish Midrash Bereshit Rabbah, a compilation of Rabbinic interpretations and aggadic commentaries on the Biblical book of Genesis edited by Rabbinic sages during the late 4th or early 5th century C.E. in order to reflect upon the contemporary events of their time. It will be argued that the Rabbis who formed this text in its final stage merged older traditions and brought them into one coherent composition which may best be explained by the perspective of their time, after the Christianization of the Roman Empire.