Abstract The history of plantation slavery and European colonization in the Caribbean has left in its wake a rich and complex linguistic landscape, a colonial education structure, and a set of contradictory (creole/colonial) identities and language attitudes that make it fertile ground for a critical examination of language education policy development in the region. Using Jamaica, a former British colony as an illustrative case, this article takes a critical look at the historical and current framing and development of the multilayered “onion” that is language education policy in the Caribbean – a uniquely creole/colonial region with conflicting language ideologies. I examine the goals, actors, processes, and challenges and possibilities of LEP implementation (Nero, Shondel. 2018. Challenges of language education policy development and implementation in Creole-speaking contexts. In Jodi Crandall & Kathleen Bailey (eds.), Global perspectives on language education policies, 205–218. New York: Routledge and TIRF – The International Research Foundation), and also look ahead, recommending ways that we might craft viable 21st century education and LEP goals for the Caribbean and other former colonies around the world, given their colonial legacy and transnational present and future.