This article examines the role of playing Indian in the development of progressive education in the U.S at the turn of the twentieth century. Experiential education provided an important incubator for a particular type of playing Indian, what I dub pedagogical playing Indian. The site of this analysis is the Laboratory School at the University of Chicago, overseen by John Dewey from 1896 to 1904. Here Indian play aligned linear historicism and genetic psychology with Dewey’s emerging experimental method. The central role of Indian play was epitomized by the school’s history curriculum, where instructors encouraged students to imagine themselves as an Indian tribe through use of a sand table. In an ironic historical twist, Estelle Reel, superintendent of Indian Schools, then introduced the sand table and other Deweyan insights into federal Indian schools. This entanglement, effaced by the innocence of play, complicates the legacy of Dewey’s educational innovations with the dispossessive logic of Indian schooling.