Through this work I intend to consider ancient Roman history through a modern postcolonial lens in order to better understand the particular nature of Roman Italian colonial frameworks and power dynamics. By placing ancient history in conversation with modern perspectives on postcolonial theory and subversive colonial dynamics, I intend to develop a refined conception of Romanization and reinforce the human aspect involved in this ancient process of colonization and Roman expansion. In particular, I consider Roman relations with Italian communities during the second and first centuries BCE, through a variety of case studies in order to contextualize the specific nature of this cultural contact and exchange. Then, as a point of comparison, I consider postcolonial theory and perspectives. Specifically, I will analyze a work by Gloria Anzaldúa in order to understand the human experience involved in processes of subversive colonization and wars of cultural hegemony. It is my goal to develop a refined understanding of the experiences of Italian individuals in this period as informed by contemporary perspectives of postcolonial theory.