This article explores psychoanalyst D. W. Winnicott’s ideas about play and “transitional space” or “potential space” in relation to reading, pedagogy, and the legacy of apartheid in South African universities. Following the work of Carol Long, who argues that “apartheid institutions can be understood as the opposite of transitional spaces,” the author draws on her experiences of teaching in the English Department of the University of the Western Cape to reflect on how pedagogy is shaped by institutional culture. The article focuses particularly on “close reading” in the South African university classroom and how a rigid understanding of it has sometimes closed and constrained the experience of reading for students in order to argue for a more open model of “close reading” that values the immersive and creative aspects of reading as well as the analytic, following Winnicott’s understanding of meaningful cultural experience as rooted in play.