This article aims to further understand the Irish immigrant experience with U.S. slavery by studying Irish overseers on southern plantations. The Irish relationship with U.S. slavery varied according to circumstances. However, as foreign-born outsiders, Irish immigrants in the South had to accommodate the region's slaveholding culture. This article takes the story of the Irish as urban pioneers of the antebellum South out into the southern countryside. Those who sought employment as overseers had no qualms about profiting from racial slavery, and the nationality of a successful overseer was immaterial to planters. Irish overseers were not categorically different from native-born southern overseers. Indeed, Irish overseers had to be as ruthless as their American counterparts if they hoped to be successful. The expansion of the southern economy in accordance with the rise of the ‘second slavery’ created more significant opportunities for Irish immigrants to become overseers and demonstrates the essential whiteness of the Irish in the South.