This thesis looks at the experiences of Chahta students at Choctaw Academy and Spencer Academy in the late eighteenth century, into the nineteenth century. Through the documentation available in the Western History Collection archive at the University of Oklahoma this thesis offers a brief case study of both schools that explores the unique relationship with western education fostered by Chahta students. Unlike typical Indian boarding schools that were run by the United States government for the purpose of total assimilation, Choctaw boarding schools used a more liberal assimilation resistant curriculum, and were funded and operated primarily by the Choctaw government. This thesis argues that Chahta students at Choctaw boarding schools found ways to incorporate their traditional values into their daily routine, which created an environment of political and cultural survival for Chatah people. By retaining certain elements of their peoplehood while attending western educational institutions during the eighteenth and nineteenth centuries, Chatah students experienced select useful acculturation of western culture yet resisted total assimilation into western society.