He started acting in theater productions for Portland Stage Company and Yale Repertory Theatre before being cast in Person of Interest. At Yale, he befriended fellow actor Lupita Nyong'o, with whom he would later star in Black Panther and Us. Winston returned to his native Trinidad and Tobago in 2012 for the theatre production of An Echo in the Bone starring alongside actress Taromi Lourdes Joseph and directed by fellow Yale alumna Timmia Hearn Feldman.
Duke stars in Marvel Cinematic Universe's Black Panther and Avengers: Infinity War as M'Baku. In 2019, Duke starred in the blockbuster horror film Us, directed by Jordan Peele.
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