Focusing on the province of Pinar del Río, the epicenter of Cuban tobacco cultivation, this work intends to correct the existing historiography that has traditionally either marginalized or assigned false stereotypes to the size and scale of Cuba’s tobacco economy primarily by disavowing the use of enslaved labor. As a regionally specific and conceptionally reconfigured site, Pinar del Río represents a new narrative of Cuban tobacco as well as an additional frontier, a new geographic zone, of slave commodity production within the Atlantic world of the nineteenth century. Through a pattern of interconnected developments framed here as latifundia, including increases in farm size, production, and labor force, the agricultural economy of Pinar del Río matured into a plantation-scale system at the same time as a second phase of enslavement was emerging in the larger region. Marked by a concentration and expansion of slaves on estates that continued to increase in size and efficiency over time, tobacco cultivation in this location not only competed with the dominant archetype of Cuban plantation slavery, sugar, but in terms of scale, also with other similar, slave-based commodities in a world market.