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Gentrification literature of certain cities has focused on middle- class parents who, believing that there will be improvement in an urban neighborhood and its schools, are willing to enroll their children in public schools (Cucchiara, 2013; Makris, 2015; Posey-Maddox, 2014; Stillman, 2012). This project focuses on middle-class parents who choose to send their children to schools in Yonkers, New York, a struggling high-poverty urban school district with a poor reputation. This work uses data from interviews and focus groups to explore why a small subset of middle-class parents, who are generally thought to have other options (Ball, 2003; Carter, 2012; Kahlenberg, 2001) remain in a struggling public school system, how they negotiate their school choice options.