In this article I offer thoughts on my recent conceptualization of culturally sustaining pedagogy (CSP) (Paris, 2012a), building from empirical work with youth of colour in US contexts, and consider what this conceptualization might mean for Jamaica and other countries where Creole Englishes are widely spoken as the lingua franca. Beginning with my own learning about Jamaican Creole and language variation as a child visiting my father’s native Jamaica, I move to sharing some of my research findings from studies of African American Language among youth in California. I then provide a summary of CSP and, finally, the learning and thinking I was fortunate enough to engage in while presenting a paper at the Literacy Symposium 2013, University of the West Indies, Mona, in Kingston, Jamaica. It is this learning and thinking that I hope opens up future collaborations between Jamaican and US-based scholarship on asset-based approaches to teaching and learning with students in both countries who continue to be marginalized by systemic inequalities based largely at the intersections of race, culture, and language.