Background: After the turn of the 21 st century in New York City, mayor Michael Bloomberg launched major initiatives to open new small schools and new charter schools as a central piece of a strategy to transform schooling and produce dramatically better results. Although more than 550 new public schools and charter schools were established in New York City between 2003 and 2015, with some increases in graduation rates, the focus on new schools has subsided, many aspects of schooling remain the same, and significant inequities in performance persist. Purpose/Objective: This article explores the confluence of factors that help CO explain how some new practices emerge even as many aspects of what Tyack and Cuban called the "grammar of schooling" endure. Design/Analysis: To achieve this objective, this article undertakes a historical analysis that highlights the intersection among the goals, capacity demands, and values in the new school initiatives, and the needs, existing capabilities, and values of four intermediaries involved in creating new small schools or new charter schools. This analysis looks particularly at the different choices these organizations made about when to connect to and distance themselves from these initiatives (when to "bridge" and "buffer") and the role those choices played in the extent and nature of their own growth and the evolution of the new schools initiatives. Findings/Conclusion: Even with political support and initiatives that were supposed to provide some freedom to innovate outside conventional constraints, these intermediaries had to find ways to fit within the needs, demands, and values of the school system at that time. At the same time, the intersections in the evolution of these organizations and the wider system also help to explain how they were able to influence the evolution of the policy environment, sustain themselves, and create some new practices, products, and services even as the focus on new school creation subsided.