In the latter half of the nineteenth century, New Orleans held one of the largest Italian populations in the United States. These immigrants, which included merchants, musicians, and artists, primarily arrived via the ship route from Palermo, Sicily, to New Orleans, Louisiana. While artistic production during the period of mass immigration through Ellis Island (c. 1890-1920) has been relatively well-studied by art historians, there has been little attention given to the impact of this earlier, southern-oriented migration pattern. The presence of these Italian immigrant artists in New Orleans provides a complex perspective on shifting racial issues during the nineteenth century. While Italian immigrants were victims of discrimination and violence due to their darker skin and immigrant status, they were also sometimes perpetuators of discrimination; however, some proved to be important supporters and allies of Black artists in the city. Whereas some, such as Jean-Baptiste Fogliardi and Antonio Meucci, served as teachers for Black artists including Louis Pepite and Julien Hudson, others, such as Achille Perelli and Dominico Canova, engaged in harmful practices such as the creation of Confederate monuments. This project explores the ways in which Italian immigrant artists lived and worked in New Orleans, and how they variously experienced, combatted, and perpetuated discrimination. Through a study of four pairs of Black and Italian artists, I trace the evolution of the Black/Italian cultural dynamic in nineteenth century New Orleans. In the Antebellum period, Italian immigrants mentored and collaborated with free artists of color; following the Civil War, as anti-Black and anti-immigrant sentiments rose, Italian artists began to distance themselves from Black artists and to accept commissions that furthered white supremacism. These shifting relationships reflect the complicated and continuously evolving ideologies regarding racial classification and status in the nineteenth century.