Initially focusing on positive Caymanian traditionalist interpretations of Jamaicans and Jamaica throughout the early to mid-20th century, this article thereafter traces the historical junctures at which these interpretations were negatively reworked to the point where Jamaicans in the Cayman Islands, and in general, are now being viewed derogatorily by many Caymanians. As the author attests, any foundational understanding of this reworking is inextricably linked to the historical relationship between the Cayman Islands and Jamaica, where British Jamaica controlled the then-economically struggling Cayman Islands to the former’s independence in August 1962. As noted throughout this article, although the well-todo Caymanian merchant establishment demonstrated an unmistakable animosity toward any proposal that the Cayman Islands join an initially successful independent Jamaica, many working class Caymanians spoke fondly of Jamaica in the years leading up to its independence, demonstrating their gratitude for Jamaican rule; such state of affairs confirms that although toward Jamaica’s independence Caymanian views of Jamaicans typically varied according to social class, by the 1970s a general cross section of Caymanians had come to regard Jamaica and Jamaicans to varying degrees of negativity. The author thus argues that the putative alteration of once-positive expressions of Jamaicans was inevitable, given the existence of a stark yet benign Caymanian/Jamaican differentiation in earlier, largely positive Caymanian understandings of Jamaica and Jamaicans, a differentiation bound, in its later inversion, to highlight independent Jamaica’s decline into various social, political, and economic hardships, while highlighting the economic rise of the politicallystable Cayman Islands.