Despite the seemingly endless possibilities for fruitful comparisons afforded by the Hispanic Caribbean, there exists a hardly justifiable dearth of comparative studies focusing on the region composed of Cuba, Puerto Rico, and the Dominican Republic. This interpretative essay, based on the extant secondary literature on the individual islands, seeks to begin to fill this void by tracing the trajectory of Cuba, Puerto Rico, and the Dominican RepublicÕs political cultures from a regional and comparative perspective. While the case could be made for including other non-Hispanic components of the Caribbean, this study recognizes the Spanish-speaking Antilles as a cultural region composed of societies sharing similar insular geographies and historical backgrounds. The Hispanic Caribbean region, because of its common Spanish heritage and its persistent vulnerability to U.S. expansionism and imperialism, stands out as a particularly useful unit for comparative analysis.