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In May 2015, the Obama Foundation concluded a multi-city bid by announcing that it selected the University of Chicago to host the Obama Presidential Library. In choosing Chicago over the closest competitors, New York City and Honolulu, former President Barack Obama emphasized the centrality of the city to his long-term personal and political development. However, the news of the announcement was met with mixed reaction. While Chicago’s political class celebrated the decision, residents of the city’s South Side expressed apprehension over the plans. Thus, community leaders sought to pressure Obama into signing a community benefits agreement (CBA). In essence, in exchange for public support, they pushed Obama to address their biggest concerns, and to sign an enforceable agreement requiring the Obama Foundation to provide material benefits that ease the degree to which the project would disrupt their lives and livelihoods. Using urban regime theory, this article examines how the collision between the politics of urban growth and participatory democracy played out in Woodlawn. More specifically, it discusses the demands made by city residents in response to the displacement pressures engendered by the development project. How was Obama able to avoid signing a CBA? And what role did the city's elected officials have in supporting his efforts to do so? With an eye towards improving the ability of residents to hold developers accountable, this article explores these questions.