As a contribution to critical studies of colonial discourse, this essay offers an analysis of Hobson-Jobson, the well-known nineteenth-century British colonial glossary of Anglo-Indian argot, as an instance of a colonial attempt to resolve the contradiction between benign intent and the violence of colonial rule in India under the Raj. The analysis draws on concepts in linguistic anthropology such as language ideology and generic intertextuality, as well as a Peircean approach that emphasizes indexicality as a key means of signification. The essay performs a close reading of Hobson-Jobson as a primary text and draws on secondary historical and theoretical literature to make the argument. It demonstrates both the need for more sober readings of the primary text than are typically offered and the particular value of the Peircean notion of indexicality in analyzing discourses with an eye to relations of power that constitute sociohistorical contexts. Finally, the essay argues that what is problematic about Hobson-Jobson despite all its linguistic richness is not just the history from which it arose but its active participation in facilitating and constituting both that history and its agents.