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In 1856 and shortly before his death, Samuel Townsend, an Alabama planter, left an estate worth nearly $200,000 to ten children from five enslaved women. Some of his offspring attended the newly opened Wilberforce boarding school and later, university in Xenia, Ohio. This paper sheds light on the complex and often quiet ways southern white men made it possible for children produced with women of African descent to obtain an education. Demonstrating that Townsend's actions were not unusual are the comments of Eliza Potter, a Cincinnati woman of mixed race who heard and saw much in her position as a hairdresser to elite whites. "[A]ll our institutions are filled with gentlemen's children sent from the South," said Potter in her 1959 memoir. In Oberlin, she reported having seen "between three and four hundred children. . . two-thirds of them being gentlemen's children from the South." Surviving records demonstrate these young people's experiences reflect an emergent postbellum black elite who remained aware of the challenges facing them and other people of African decent in and outside the South during the postbellum period and rise of Jim Crow. What do we make of their lives and ongoing hurdles facing African Americans in educational settings and beyond?