Background: Scholars in the fields of early childhood education (ECE) and multicultural education have argued that preschools are key sites in which children learn about race and racism. However, there is little research on how teachers negotiate conflicting tensions and enact antiracist approaches within Head Start (HS) classrooms that use comprehensive and commercialized curriculums. Study Purpose: This article is about the challenges early childhood educators face when young children (ages 3-5) bring painful and uncomfortable issues of race, racism, and incarceration to preschool. This study is part of the research project Negotiating Head Start Curriculum (NHSC), a comparative study of policy implementation in four cultural communities in the United States. Here we focus on educators' response to the "Jail Scene," a pivotal scene taped in an HS classroom serving African American children. Research Design: The method used in the NHSC project is a multivocal ethnographic research method combined with a comparative case study design. We selected classrooms in each community that implemented both Creative Curriculum® and Teaching Strategies Gold®, led by experienced teachers in Chicanx and Latinx, Samoan, and white Appalachian communities. We made videotapes of similar activities across all sites. We then used these videos as cues for focus group interviews with educators (teachers, directors, and instructional personnel). We applied constant comparative, Critical Discourse Analysis, and Voloshinovian literary analysis to 41 interview transcripts of 132 educators' talks. Findings: Analysis of transcripts indicates Black teachers are more likely to recognize racism, including the effects of incarceration and arrest on children's talk and play, in ways unavailable to teachers from outside their community. Despite extant research suggesting early childhood teachers of color are no more likely to engage with young children about racism than white teachers, our study found that Black teachers offer nuanced, careful, and responsive approaches to antiracist pedagogy. They respond in sensitive, child-led, playful ways, inserting counternarratives within the confines of scripted curricula. Conclusions: ECE teachers' disparity of interpretation has particular importance as ECE moves to professionalize the field. If elementary school patterns are any indication, the field should expect a sharp increase in the percentage of white, middle-class teachers instructing children of color. Unintentionally, these teachers may fail to recognize the play and talk to contain challenges born out of racism and inequality. We suggest policymakers, curriculum designers, and the broader field of ECE must carefully consider the approaches of teachers of color and take these approaches seriously.