This dissertation is invested in a critical examination of the interplay between literature, law, and witchcraft within Hispanic and Chilean cultures. Drawing from paradigmatic examples of the literary canon like the first American epic poem, Ercilla’s La Araucana (1569-89), and the first modern Chilean novel Don Guillermo (1860) by José Victorino Lastarria, as well as from Jesuit lexicons (1611, 1765, 1777), and judicial records (1695, 1880), this project demonstrates how comprehensively the representation of witchcraft and sorcery has been entangled in a form of colonial written capture exerted upon Mapuche beliefs and language (Mapudungun) from the sixteenth century through the early 1910s. Conversely, while acknowledging the process of colonial semiosis (Mignolo), I argue that in conceiving non-Mapuche written language (Spanish) as sorcery, through Machi traditions and language philosophy, Mapuche people have resisted and challenged the codifying archive, in a gesture of counter-sorcery. The analysis moves through sources in two ways: first, historically, seeking to trace, from the Old to the New World, a ‘grammar of witchcraft,’ i.e., the symbolic and syntactic chains that render witchcraft a potential idiom through which lettered men represented Mapuche magical traditions; and second, paradigmatically, by examining specific examples of written culture whereby this grammar is problematized and is projected beyond colonial times. This research moves away from assumed dichotomies in Latin American discussions about colonialism, such as orthodoxy/heterodoxy, orality/writing, and universal/local, underscoring instead the importance of points of inadequacy or ‘encounters of misencounters’ (Jocelyn-Holt), that afford readings not of what witchcraft is, but rather how witchcraft is at once possible and persistent within more than one tradition. As a whole, this project illuminates a neglected aspect of literary and juridical history in South America, not only by explaining the impact of European ideas of witchcraft upon Mapuche people in Chile but also their legacy and resisting voices in the letter of literary works and trials, both in Colonial and Republican periods.