After university, she wrote both for BBC’s Caribbean Voices as well as for its then Third Program, for which she both created and adapted radio dramas. She also collaborated with her then husband and novelist, Jan Carew, on a radio drama, The University of Hunger, later re-written for television as The Big Pride. Her novel, The Hills of Hebron, was published in 1962 by Simon and Schuster. In that same year, which marked the occasion of political independence for Jamaica, she returned to the island where she joined the faculty of the University of the West Indies. Although she continued to write occasionally for the Jamaican theater, her writing would take an important turn.
The anti-colonial movement that had cut across her childhood and which had provided the themes of her earlier writing, would now serve as the theoretical point of departure for her decolonizing reconceptualization of the history of Jamaica and the Caribbean, as founding regions of the Western world-system, and therefore of contemporary modernity. Doing so, she was to form part of a generation of Caribbean and Black American thinkers who sought to reinterpret the history of the modern world from the perspective of the plantation system of the ex-slave archipelago of the Americas. As part of this movement, Wynter would help to found Jamaica Journal, while contributing to others such as Caribbean Quarterly, New World Quarterly, and Savacou, all of which were involved in the same imperative.
In 1974, on the strength of many of these essays, and in the context of the myriad political and social movements of the 1960s United States, she would be invited to join the faculty at the University of California at San Diego in order to teach in the new Literature and Society in the Third World Program. In 1977, she would be invited to Stanford University where she taught both in the department of Spanish and Portuguese, and in the also new post-60s Afro-American Studies Program. Wynter retired from Stanford in 1994, and continues to live in Northern California’s Bay Area.