In 1926, Harold Keltner, a YMCA Boys Work secretary from St. Louis, and Joe Friday, a member of the Canadian Ojibwe First Peoples, channeled white middle-class fascination with Native Americans into what became the Y-Indian Guides youth program, engaging over a half million participants across the nation at the height of its 77-year history. Intended to soften the stereotypical stern father, the program traced a complicated thread of American history, touching upon themes of family, race, class, and privilege. The Y-Indian Guides was a father-son (and later parent-child) program that encouraged real and enduring bonds through play and an authentic appreciation of family. While “playing Indian” seemed harmless to most participants during the program’s heyday, Paul Hillmer and Ryan Bean demonstrate the problematic nature of its methods. In the process of seeking to admire and emulate Indigenous Peoples, Y-Indian Guide participants often misrepresented American Indians and reinforced harmful stereotypes. Ultimately, this history demonstrates many ways in which American culture undermines and harms its Indigenous communities.