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The Caribbean has long been classified as a region of weak, small island developing states, and positioned as lacking in agency, visibility and influence globally. Issues of dependent development shaped by colonial legacies and conditioned by material (in)capabilities, size, remoteness, economic and environmental vulnerabilities have undergirded the quest for viability. China’s Belt and Road Initiative (BRI) as part of the grand strategy of its diplomatic engagement with Latin America and the Caribbean (LAC) has presented many states in the Circum-Caribbean region with strategies for confronting enduring issues of post-colonial development and navigating contemporary global realities. This paper explores the utility of the concept of decoloniality in examining the extent to which the BRI amplifies and addresses the decades old struggle for economic transformation in the region. Through an analysis of China’s relationship with regional countries, primarily Cuba, Jamaica, and Guyana, the work explores new developments in Caribbean political economy by assessing the role, place and potential of the BRI in restructuring Caribbean international economic relations in this period of global uncertainty.