Malea Powell has argued that Charles Alexander Eastman "imagined new possibilities for Native resistance and survival in the face of violent assimilation strategies." To Eastman, Natives had little choice but to acculturate to white society if they were going to resist white domination and survive. But gaining full equality in U.S. society proved difficult in the Progressive Era, given continued white paternalistic regard for Native peoples, as well as enduring negative white stereotypes of Natives, particularly the notion that they were racially childlike, boyish savages incapable of measuring up to the standards of racially superior, "manly" civilized white men. Although scholars have noted the role of gendered discourse in Eastman's writings, it deserves much more critical attention, for it is an essential site of his resistance to white domination. Eastman fully recognized that Natives had to overcome white racist ideologies that circumscribed their manhood if they were to gain full equality in U.S. society. In this article, the author explores Eastman's "From the Deep Woods to Civilization." In his book, Eastman challenges this racism by negotiating the values of white middle- and upper-middle-class manhood, as well as stereotypes of Native manhood. Drawing equivalences between Santee and middle- and upper-middle-class white manhood, Eastman illustrates that Santee--and by extension all Native males--are intrinsically equal to white males in their manly attributes and thus capable of full and equal U.S. citizenship. (Contains 6 notes.)