Chicago has long been one of the national epicenters for public school reform. In many ways the reform efforts of the past decade in the Windy City have served as the blueprint for the current focus of federal education priorities. In particular, federal policy for school turnaround and transformation takes clear cues from the efforts that current Secretary of Education Arne Duncan oversaw in Chicago when he was CEO of Chicago Public Schools from 2001 to 2009. Shuttering low-performing schools (as measured by test scores), facilitating the restructuring of schools (often resulting in major shifts in personnel and student population), and promoting the growth of charter schools have all been strategies for Chicago reform and are now centerpieces of federal school turnaround guidelines. However, for such technical approaches to school turnaround to be successful, they must be accompanied by close consideration of the social, political, and cultural dimensions of school change. Without attending to these other dimensions, Chicago has experienced the alienation of its professional teacher corps and the disillusionment of many parents and grassroots community leaders with regard to public school reform, outcomes that undermine the social capital and trust that ensure broad local support for public school systems. Scores of underperforming and failing schools across the country are in severe need of turnaround and transformation. However, federal policies that introduce technical change and innovation without careful attention toward how to create change collaboratively with teachers, parents, and other community leaders miss crucial opportunities to engage those for whom the change matters most. The work of the Chicago Teachers Union, described in this article, provides a promising model of teacher and community engagement that the U.S. Department of Education can look to as they seek to create policies and guidelines that will support sustainable reform, particularly in urban areas.