In 1941, the well-known international Cold War actor Serafino Romualdi traveled to South America for the first time. As a representative of the New York-based Mazzini Society, Romualdi sought to grow a robust anti-fascist movement among South America's Italian communities, finding the most success in Uruguay. As Romualdi conducted his tour of South America, he began writing a series of reports on local fascist activities, which caught the attention of officials at the Office of the Coordinator for Inter-American Affairs (OCIAA), a US government agency under the direction of Nelson Rockefeller. The OCIAA would eventually tap Romualdi and his growing connections in South America to gather intelligence concerning Italian and German influence in the region. This investigation sheds light on the critical function that Romualdi and his associates played in helping the US government to construct the initial scaffolding necessary to orchestrate various strategies under the umbrella of OCIAA-sponsored cultural diplomacy. Despite his limited success with Italian anti-fascist groups in Latin America, Romualdi's experience in the region during the early 1940s primed him to become an effective agent for the US government with a shrewd understanding of the value in shaping local labor movements during the Cold War.