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Newbery Medal–winning books provide cultural models for children’s developing cultural understandings of themselves and others. This article presents results of a critical content analysis that used sociocultural and historical lenses to examine representations of race/ethnicity, gender, and ability of main characters across the Newbery-winning corpus and how these representations have changed over the history of the award, 1922–2019. Findings present a lack of consistent diverse representation across all fields, with increased diverse representation in the most recent decades. The discussion contextualizes findings against historical events. Understanding the representations of diversity in these texts and the historical contexts within which such texts have emerged provides grounding to problematize the status quo of the curriculum and suggests a need for critical questioning and grand conversations.