“He tried to outrun a train,” Theodore Blindwoman told David Joseph Charpentier the night they found out about Maurice Prairie Chief’s death. When Charpentier was a new teacher at St. Labre Indian School in Ashland, Montana, Prairie Chief was the first student he had met, and the one with whom he formed the closest bonds. From the shock of moving from a bucolic Minnesota college to teach at a small, remote reservation school in eastern Montana, Charpentier details the complex and emotional challenges of Indigenous education in the United States. Although he intended his teaching tenure at St. Labre to be short, Charpentier’s involvement with the school has extended beyond thirty years. Unlike many white teachers who came and left the reservation, Charpentier has remained committed to the potentialities of Indigenous education, motivated by the early friendship he formed with Prairie Chief, who taught him lessons far and wide, from dealing with buffalo while riding a horse to coping with student dropouts he would never see again. Told through episodic experiences, the story takes a journey back in time as Charpentier searches for answers to Prairie Chief’s life. As he sits on top of the sledding hill near the cemetery where Prairie Chief is buried, Charpentier finds solace in the memories of their shared (mis)adventures and their mutual respect hard won through the challenges of educational and cultural mistrust.