We explore the impact of social institutions on economic performance in Jamaica through a reinterpretation of the plantation economic model. In its original form, the plantation model fails to develop a causal link between the plantation legacy and persistent underdevelopment. Despite its marginalization, the model remains useful for discussions on growth and development. Consequently, we offer a reappraisal using the causal insights from Kenneth Sokoloff and Stanley Engerman. We use two examples to demonstrate how inequality encourages the formation of institutions that are inconsistent with growth, and an empirical analysis to confirm the hypothesized relationship between inequality, institutions, and economic development. Since inequality is expected to influence growth indirectly, we use a structural specification, which follows William Easterly's recent test of Sokoloff and Engerman's argument. Our reliance on a time-series specification is unique. We demonstrate that the expectation that, on average, inequality and growth is negatively related and that institutions may compromise growth are accurate for Jamaica, the most cited Caribbean nation in the current discourse. Our results carry several policy implications, including support for the recent calls in Jamaica for political restructuring. However, both the paucity of similar studies and the importance of the implications for sustainable growth and development demand further analyses.