Winston teaches in the Liberal Arts Transfer Program at Seneca. In addition to core courses, including Academic Research and Writing, and World Literature, he teaches electives for English & Liberal Studies (ELS) on blues, jazz, and identity politics. Before coming to Seneca, he taught as a sessional professor in the humanities department at York University, co-owned the literary bookstore Writers & Co., and hosted "Expandable Language," a jazz program on CKLN Radio. In addition to a degree in English and literary studies from the University of Toronto, he holds a graduate diploma from Exeter College, Oxford University, in English Literature.