The authors discuss an urban public school district's efforts to reinsert play after its mandated disappearance for fourteen years under a scripted curriculum imposed to meet the goals of the No Child Left Behind law. The authors analyze field notes, teacher and administrator interviews, coaching records, and surveys to chart the impact on teachers of the efforts to revive play in their classrooms. The study suggests that these attempts increased the teachers' understandings of child development and the connections between play and social-emotional development. The authors note the role of teachers in arranging play-friendly classrooms and the problems teachers faced including the lack of any district curriculum; the complexities of public-private partnerships; the lack of understanding about play by parents, principals, and administrators; and children's challenging behavior and volent play themes. Finally, the authors consider the sociopolitical factors influencing the sustainability of play in large urban classrooms.