The Danish West Indies has often been left out of comparative investigations of slavery between the United States and the Caribbean. This study examines the natural and social environments of two enslaved communities in an effort to reveal the greatest threats to the lives of enslaved peoples and how each community responded differently to such threats. A mix of archaeological and documentary evidence recovered from James and Dolley Madison's Montpelier plantation in Virginia and the Christiansted National Historic Site in St. Croix has revealed an archaeology of struggle, a form of double consciousness in the minds of enslaved peoples, oscillating between self-preservation and resistance in the daily fight for survival. The diversity of livelihoods across the African Diaspora is illuminated by comparing the lives of Afro-Caribbeans enslaved by the Danish Crown in St. Croix, within an urban, non-plantation, and sugar-based industry, to that of African Americans enslaved by a US president in Virginia, within a rural, plantation, and tobacco-based industry. The results indicate that enslaved peoples in different regions did not have the same primary concerns or face the same environmental dangers and, as a result, invented different ways of coping with the unique struggles they faced. [African Diaspora, Danish West Indies, Caribbean Archaeology, urban slavery, Virginia]