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The purpose of this paper is to explore the schooling experiences of a small group of men who grew up in Windsor, Ontario, during the immediate postwar period of 1945–1965. Drawing from analytical insights provided by Raewyn Connell’s work on men and masculinities and employing the historian’s craft, this small-scale study relies on interviews conducted with nine men and three women who grew up in Windsor, Ontario, during the postwar period and who were selected to represent a diversity of cultural backgrounds. The study finds that much of what it meant to be a school boy in Ontario’s postwar period rested on gender relations infused by patriarchal understandings of masculinity as it intersected with social class and race.