This paper provides a critical analysis of Freire’s Italian reception and argues that reinventing Freire requires us to historicise and to contextualise his legacy, which in Italy makes sense in consonance with the already existing Italian popular education tradition. Based on the case study of his 1989 honorary degree at the University of Bologna, this article investigates Freire’s influence in academia by comparing two generations of scholars and activists who have received Freire in different ways. Drawing on interviews to key informants who belong to two generations of educators influenced by Freire, this paper argues that the Italian Freire’s renaissance is associated with the growing need for a generation of militant educators to find a theoretical framework to oppose the hegemony of both neo-liberal and neo-nationalist discourses in education. The reasons for Freire’s reinvention in the academic sphere are investigated and the profile of the second generation of Freireans in Italy traced out, highlighting both continuities and tensions with the first one. Finally, the motives for Freire’s success in today’s Italy are presented in seven main theses, showing that many of them are made possible by virtue of the political, cultural and pedagogical background that made Freire’s re-invention in an Italian context possible.