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This paper focuses on the linguistic work of John Gilchrist (1759–1841), one of the first British grammarians to produce a detailed and systematic study of the language known in the 18th century as ‘Hindustani’. An interesting feature of Gilchrist’s grammatical texts is the fact that, within the framework of a grammatical account of a South Asian language, they often include short passages discussing contemporary problems in the analysis of English. In these passages, Gilchrist engages directly with the work of writers such as John Horne Tooke, Samuel Johnson, Robert Lowth, and Thomas Sheridan, taking up a position in relation to their work and drawing upon his research on Hindustani to support or challenge their analyses of English. In one typical example, discussed in this paper, he mobilises evidence from his own work in support of Thomas Sheridan’s innovative account of the vowel in words such as mine and thine, an analysis that characterises this sound as a diphthong rather than a simple articulation. In the light of Gilchrist’s later visibility as a political radical, some commentators have seen his allusions to Horne Tooke as evidence that his linguistic work has a demonstrably radical character. However, the diversity of the thinkers with whom Gilchrist engages suggests that it is better to interpret his interventions in the analysis of English as attempts to build a reputation as a scholar, not only in the colony but in the metropolis as well. As such, the passages in which Gilchrist discusses the nature of English can be seen as political in the sense that they helped him to find a platform from which he could voice his radical ideas. But they do not always constitute a radical account of the language itself, their importance lying in the opportunities they offered for self-promotion and, indeed, self-transformation.