The dropout social problem has been the focus of researchers, business and community leaders, and school staffs for decades. Despite possessing significant academic high school capabilities, some gifted students drop out of school. The research problem for this study includes how and why former gifted urban high school students chose to drop out. The conceptual framework for this case study is Bronfenbrenner's (1996) human ecology theory. The purpose of this study was to gain an understanding of what led former gifted urban students to drop out of high school. Using purposive sampling, four participants, two men and two women, were selected for semistructured interviews. The sample included an African American, a Filipino, a Caucasian, and a Haitian/Cuban/Syrian. Their ages ranged from 38-77 years old. The semistructured interviews were analyzed using first, second, and pattern coding. The resulting themes were (a) family discord, (b) school not interesting, (c) no role model, and (d) minimum family participation. The former gifted high school students' dropout experiences were rooted in the microsystem perspective of the human ecology theory. The implications for social change from this study's findings may help inform those who manage and teach gifted programs about the mindsets of students in gifted services.