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Although urban renewal as practiced in New Haven in the mid-twentieth century has been widely criticized, Wooster Square is frequently held out as an exceptional success story – the one renewal project that involved residents and helped turn around a struggling area, making it one of the most desirable neighborhoods in the city. Yet more people were displaced from the Wooster Square in the fifties and sixties than from any other neighborhood in New Haven. Hundreds of buildings were destroyed, and thousands of people were displaced. So why has Wooster Square been spared much of the criticism to which other urban renewal projects have been subject? In this paper, I identify three main reasons that mid-century redevelopment in Wooster Square is widely perceived as a successful urban renewal initiative. First, urban renewal efforts in Wooster Square engaged many middle- and lower-income homeowners, providing them with numerous resources and with an important rung on the ladder of social progress. Because the interests of these residents aligned with those of the Redevelopment Agency (RA), close collaborations formed easily, lending credence to the assertions that the RA was responsive to the desires of local residents even as poorer Italians, black people, and others who gave the neighborhood its unsavory reputation were left out. Second, residents who were displaced by the highways and by urban renewal efforts were generally poor and frequently rendered invisible by the process of their displacement. Whether they fled in advance of the next big change, were relocated to other poor areas or, in the case of the lucky ones, found preferable living situations elsewhere, those who left the neighborhood were no longer as able to share the other side of the story. As a result, those who remained in Wooster Square or moved to it as a result of its gentrification were primarily responsible for telling the story of the neighborhood’s success. Finally, the RA made a concerted effort to make its successes in Wooster Square known, and the narratives put forward by supporters of urban renewal rarely included meaningful discussion of those who were pushed out of the neighborhood. The mass media, captivated by the story of a bad neighborhood that had made good, focused overwhelmingly on the poor quality of the housing pre-renewal, the involvement of local people in the planning and implementation of renewal projects in the area, and the beautiful architecture in the neighborhood. These treatments cemented a popular image of Wooster Square as the success story of the urban renewal period, even though it involved significant displacement and disempowerment. Rather than an unmitigated success that avoided all of the missteps that befell other urban renewal projects in New Haven, urban renewal in Wooster Square is more properly understood as a complicated contest for the neighborhood’s future, the story of which would be told by its winners.