John Milton Oskison (1874-1947) was a Cherokee writer, journalist, and activist and the author of novels and biographies as well as numerous short stories, essays, and articles about a great variety of subjects. Oskison thought of himself as "an interpreter to the world, of the modern, progressive Indian." The kind of representation Oskison gave of the Indians--the "new Indians" stepping up to take their places in the social and economic life of the West--earned him the label of assimilationist. However, scholars have argued that Oskison did not write, or wrote very little, about Indians. Put in the simplest terms, it may be said that Oskison did not write of the precontact past--which he never knew--with nostalgia and that he described Indians who had in themselves the means to be at ease in American society. He, and the Cherokee citizens he knew, were exemplars of such Indians. To determine how exactly Oskison's life and philosophy fit or do not fit with an embrace of assimilation is the purpose of this essay. After clarifying the definition of assimilation, the author will examine what Oskison seemed to think about what Daniel Heath Justice calls the "wholesale rejection of Indigenous values," arguably a sure sign of assimilation. Then, to understand Oskison's position regarding assimilation, it will be necessary to analyze what he wrote about education, since assimilation policies always heavily relied on the schooling of Indian children. The author will then explain that Oskison advocated that Indians and European Americans should live side by side, each contributing to a common society, in a process that he referred to with the notions of absorption and amalgamation. (Contains 89 notes.)