Background/Context: The lack of court-ordered support for race-based policies that maintain and create integrated schools has forced communities of color to seek other avenues to obtain equitable education, such as school choice. Individual states and the federal government, as seen in grant provisions through the American Reinvestment and Recovery Act, are encouraging the expansion of choice at the very time that options for increasing student diversity, particularly racial diversity, are being narrowed by the courts. Purpose/Objective/Research Question/Focus of Study: The article uses critical race theory to examine the outcomes of specific school reforms, based on market theory models of school choice, that were designed to alleviate schooling inequities in urban districts. Setting: The context of Milwaukee, Wisconsin, serves as a microcosm of urban districts that have embraced school choice to create more equitable schooling options. Milwaukee, like most metropolitan areas, has a history of court-ordered desegregation that served as a temporary solution to racially segregated schools. Given the federal and district court turn from supporting race-based desegregation policies in schools, Milwaukee and other metropolitan districts are looking for new models to serve students of color in their districts and cities. Research Design: This article is a conceptual paper that incorporates data from a variety of sources to support the authors' conclusions. Data Collection and Analysis: Data for this project were taken from the U.S. Census Bureau, documents from newly created small high schools, such as Web sites and curriculum designs; current newspaper articles discussing issues of small high schools; archival newspaper articles documenting the creation of the 1990 choice and charter programs; professional experiences as a member of the Bill and Melinda Gates institutional selection and small-school team support system; and an empirical study that documents teachers' attempts to provide curriculum and instruction in newly created small schools. Conclusions/Recommendations: In combination, these data sources tell the story of market theory reforms that will continue to struggle to meet reformists' goals to serve all Milwaukee populations so long as policy makers and the courts continue to deny the irrefutable power that race and class exercise in parental choice in U.S. urban schools.