In the late 1990s and early 2000s, the Chicago Housing Authority demolished all of its high-rise family projects and undertook a massive redevelopment plan. The Plan for Transformation turned the former sites of high-rises into mid-rise, mixed-income communities to address the issues of crime and poverty concentration that had plagued the projects. While the resulting communities have largely avoided the symptoms of social decay that beset their predecessors, their construction has carried with it a decrease in public housing units and a tumultuous relocation period for many public housing residents. This paper seeks to evaluate both the successes of the CHA’s Plan for Transformation and its flaws in implementation and planning, questioning who the Plan was designed to benefit. Using the Oakwood Shores community as a case study, this paper analyzes the changes in demographics and social outcomes at the Oakwood Shores developments, comparing them with data from the surrounding area to determine whether the resources invested in redevelopment have resulted in measurable social change in Chicago public housing. This paper concludes that the results of the Plan for Transformation on the ground are somewhat disappointing compared to what was promised, as demographic changes are equivalent to the trends in nearby neighborhoods. Furthermore, by reducing the number of public housing units and reintroducing tenant screening, the CHA has not succeeded at making high-quality housing available for the most vulnerable Chicagoans. Chicago's public housing is no longer as dangerous, nor a source of bad press, nor an aesthetic blight, but it also no longer serves the same social function.