This paper shares results from a critical content analysis of Newbery-winning titles from 1922-2019 for representations of race/ethnicity, gender, and disability. Each title was coded for the inclusion and representation of race/ethnicity, gender, and disability at both the book and main character levels. Lenses of critical race, gender schema, and critical disability theories were used to classify the ways race/ethnicity, gender, and ability of diverse populations are portrayed and represented in Newbery-winning titles. Results were then compared to U.S. Census and National Center for Education Statistics data about today's public-school population. Representations of diversity in Newbery-winning titles are not confluent with the race/ethnicity, gender, and disability of children in U.S. schools. Given the prominence of Newbery-winning literature in elementary schools, children are likely to come across these unrepresentative characters.