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This essay situates Baldwin’s writing within the political climate of the early 1970s and within a period discourse that understood prisons as important sites of political struggle. We show that, for Baldwin, prisons elucidate the historic and intimate interplay of masculinity, sexuality, and race. They constitute at the same time sites of homosexual/homosocial closeness and love, as well as masculine violence and hate. We argue that Baldwin’s writing about prison in the early 1970s, and particularly his direction of Canadian playwright John Herbert’s Fortunes and Men’s Eyes in Istanbul, served as vehicles for contemplating sexual alterity and for imagining a morally and politically renovated social order.