This article reports on five years of intermittent observations of Chicago school reform by a team consisting of a social historian, social psychologist, and urban anthropologist. It chronicles a method for tracking the implications of school reform over time. The authors started with the goal of reporting on Chicago to an audience outside the city: to their surprise, they discovered an audience inside the city eager to hear their observations. They focused on both the system-wide, structural view of reform and the ground-level view from the schools and local community. Their method consisted of identifying a network of informants inside the city, attending meetings and public events, and visiting schools, and they followed three schools closely for more than two years. When they realized that the phases of their own learning process had matched the phases in the history of Chicago school reform's first five years, they decided to structure their observations as a narrative exploring reform through their developing and changing understanding. Among the themes they discuss are the unique character of the reform; the role of reform's public/private civil society; the many stories of reform's origins; the multiple layers of reform, and the problem of evaluation.