In this edited collection, we privilege the use of oral histories to grapple with the complexities of the patterns and legacies of educational (under)achievement. The oral histories featured underscore the power of missed or stolen opportunities as marked by one’s race, gender, and socioeconomic class. As historical subjects shaped by the particular time and place of their early childhood and adult experiences (such as Jim Crow segregation in the South, Cold War, civil rights, and women’s movement in the United States and Australia), they note the strict racial language and gendered codes that inhibited the full range of not only their educational potential, but their full human potential. In spite of such structural means aimed at failure, the narrators also reveal a pattern of educational and community achievement, broadly conceived, to pave future legacies for success. Where quantitative studies fall short, these histories necessarily embed the rich layers of the processes by which we live and through stories. Stories mark our past, present, and future. Insomuch as they create the sum of all our parts, it also provides important placeholders to understsand the context of who and why we are.