The postwar North Adriatic Region was a primary source of tension and hostility between Italy and Yugoslavia. For several decades, until the Osimo Treaty of November 1975, Rome and Belgrade remained diplomatically distant despite the changes in the international system and the new position following Yugoslavia’s rapprochement with the West. From the Yugoslav perspective, the new postwar Italian republican democratic institutions were not significantly improved from the previous fascist ones, and the responsibility for the 1941 invasion was unresolved. Both perceived the other as excessively nationalist, and Italy accused Yugoslavia of territorial revenge regarding the disposition of Istria and Dalmatia. The contested areas of Friuli-Venezia Giulia and the city of Trieste became the focus of a territorial dispute between the two states, full of symbolism, opposing narratives, and ideological conflict, narrated through the story of a small group of Italian Communists who were building a “true socialism” in Yugoslavia and were overwhelmed by the “wheel of history” after the Cominform’s break in 1948. This is an emblematic story of those years of confrontation, idealism, and realism at the dawn of the Cold War.