In this chapter, the authors use Black Feminist Thought (BFT) to examine the mathematics education and the educational attainment of African American females in a matrilineal line that spans five generations. A cross analysis of school experiences, from a maternal great-great-grandmother to her great-great-granddaughter, reveal a portrait of segregation, desegregation, and resegregation. The impact of these educational contexts on the mathematics literacy and mathematics identity of four African American women and the hope and promise of a young girl in the class of 2026 are also presented. From sharecropper schools in Mississippi to prestigious universities in the eastern United States, the challenges and successes of one family's struggle to obtain mathematics literacy and the American dream are discussed through the historical lens of "Brown v. Board of Education." Using this historical context, the specific experiences of these five family members encourage a dialogue about a larger narrative--the mathematics attainment of all Black children. [This article was first published in: J. Ballenger, B. Polnick, & B. Irby (Eds.), "Women of color in STEM: Navigating the workforce" (pp. 79-107). Information Age Publishing, 2017.]