Assuming the strength of small by design schools for poor urban students of color to be a settled question, this project attempts to analyze the sustainability of small by design schools in a large, complex urban district. Asking what causes small schools to converge toward or diverge from the small by design model, I analyze three sets of design elements over five distinct periods of development for small schools in Chicago. The forces and stakeholders encouraging or eroding small by design schools are identified through policy and document analysis, along with three case study schools. Observations include that principals, district behavior, advocates, charter legislation and state law have had strong effects over supporting or eroding design elements, and teachers, district policy, foundations and the teachers' union have weaker effects. While a few small schools persist from each period, the small by design model is not institutionalized in Chicago Public Schools. The implications for policy and the sociology of school organizations is explored through the organizational field concept in new institutionalism, revealing the deleterious effects of bureaucratic processes and neoliberal cultural pressures on this progressive education form. Policy and structural ideas suggested by the analysis are included. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]