Winston worked as an educator in the Quebec school system and was also a prominent community organizer in the Montreal Black community. Winston recalls that his BCSE was founded in the 1960s when Caribbean immigrant students were being unfairly streamed into special education classes due to poor results on biased standardized tests. As an educator in the school system, Winston advocated for the promotion of Black teachers so that they could advocate for Black students. Winston describes the impact of the Sir George Williams affair and its influence on the founding of Montreal BCSEs. He recalls informal meetings with like-minded Black educators as the starting point for supplementary educational initiatives.