Existing development theories predict that factors such as natural resource wealth and the legacies of European colonizers inhibit development. However, the case of Trinidad and Tobago challenges these theories, as a resource‐rich former colony that has achieved high levels of development. This article examines what accounts for Trinidad and Tobago's development trajectory. Advancing a novel analytical approach – a postcolonial sociological approach – this study emphasizes what existing theories miss, namely, the role of organized labor in enabling Trinidad and Tobago to escape the development trap. The findings suggest that development studies attend to how colonial labor legacies shape post‐colonial development.