The purpose of the essay is to reconstruct the personal history of the magistrate Carlo Materazzo in service in Tripoli before and after the Second World War. His biography allows us to highlight the characteristics of an Italian “colonial judge” during the fascist regime, the British military occupation and the process of independence of the so-called Italian “Quarta sponda”. What makes the story particularly interesting, in addition to the different forms of collaboration of Materazzo with apparently very different political regimes, is the publication by the magistrate of a memoir about his experience in Libia. By dialoguing archival documents and the memories of Materazzo, I tried to retrace a single aspect of the slow italian transition process from fascism to democracy.