The thrust of migration from the British-colonized Caribbean to America can be dated to the early twentieth century but accelerated from 1964 with the removal of country quotas. Jamaicans represent the largest number of British Caribbean migrants to the United States and possess the most distinct and persistent cultural identity. This research asks the question, 'What accounts for the persistence of Jamaican cultural identity in migration?' In seeking to answer this central question, this study considers the theories of Philip Kasinitz, and others who offer various reasons for British Caribbean migration to America, and the survival of their cultural identities in the migrant space. Unlike the existing literature, using secondary and primary sources, statistical analysis, and oral history methods, this research focuses specifically on Jamaican cultural retention in New York City, 1964-2000. It examines key markers of 'Jamaican' cultural identity to argue that both the historical foundations of Jamaican culture prior to and during this period, and the distinct mode and context of incorporation for Jamaican migrants into New York City lie at the heart of such cultural persistence.