Each successive wave of immigrants to America has faced prejudice founded in fear and uncertainty. Immigrants from Italy were particularly discriminated against in the early years of their arrival, from 1880 through 1920. They faced violence, racial slurs, and media attacks based on an unsubstantiated stereotype of criminality. This project set out to discern how the Italian immigrant community in America, through the case study of the city of Cleveland, evolved from being despised and racialized to being accepted as white Americans. Archival research, historical newspaper articles, and manuscripts such as letters and Americanization pamphlets largely inform the writing, in addition to secondary scholarship and memoirs. The paper lays out first the context in which Italian immigrants came to Cleveland and where in the ethnic fabric they fit, then the negative reputation and stereotyping that the Italian population faced, and finally the Americanization processes of the Italian community in Cleveland. Economic mobility, support from hometown societies, individual community leaders, and the racial dynamics of Italians’ white skin and subsequent discrimination against African Americans each contributed to the evolution of Americanization for Italian immigrants. That trajectory is a pattern that every European ethnic group has faced to some degree through the history of American immigration. The arc of shifting ‘whiteness’ and gradual Americanization may provide a framework for understanding present-day immigration and ethnically based discrimination.