This is a detailed study of Gilchrist’s grammatical praxis which presents a picture of the complex relationship between grammatical inquiry and the politics of colonial discourse in the early years of the Indian Empire. It develops a method of reading colonial grammars that acknowledges both the technical and the political dimensions of the text. It explores the political consequences of the choices that grammarians made that could easily elicit reactions of fear, confusion, and even contempt in colonial observers. It presents a picture of the complex relationship between grammatical inquiry and the politics of colonial discourse in the early years of the Indian Empire.