Although Prosper was a supporter of Pope Leo, the nature of their relationship is in need of reconsideration. Most scholars have considered Prosper of Aquitaine’s contribution or influence on Leo’s homilies and letters, especially the Tome, by considering stylistic similarities. Indeed the tract On the Calling of all Nations, a work once thought to have been written by Leo, is now attributed to Prosper but its stylistic similarities convinced certain scholars, notably N.W. James (1993) that Prosper was responsible for some of Leo’s writings. However, this stylistic analysis is not compelling; B. Green (2008) has argued, rightly in my view, that Prosper was not responsible for anything that we now attribute to Leo. However a full assessment of the relationship between these two fifth century leading figures should take into account not only stylistic and theological matters, but how both men view events and actions. My paper will reconsider the relationship between Prosper and Leo in the light of a new appreciation of Leo’s independence as a writer, thinker and actor. I will focus in particular on the ways in which the two differ in their views of contemporary events and people.