A literary celebrity associated with England’s famous John Murray publishing house, Sir Francis Bond Head (1793-1875) is nowadays best known for his controversial tenure as lieutenant governor of Upper Canada from 1836 to 1838. Often blamed for the outbreak of the 1837 Upper Canada Rebellion and justly criticized for his efforts to remove Anishinaabe people from their traditional territories, Head cuts a sorry figure in Canadian historiography. This negative assessment is in stark contrast, however, to scholarship on Head’s earlier Argentine period (which Canadian studies scholars have seldom considered), during which time he led the Rio Plata Mining Association’s efforts to exploit a series of gold and silver mines located in the Andes. Despite Head’s status as a member of the European capitalist vanguard of British businessmen-cum-travel writers who worked in South America in the 1820s and ’30s, scholars of nineteenth-century South America have praised his sympathetic depictions of Indigenous people and his self-reflexive criticisms of European capitalist imperialism. In a discussion of his bestselling 1826 memoir Rough Notes Taken during Some Rapid Journeys across the Pampas and among the Andes, my talk will investigate Head’s outspoken criticism of contemporary racial theory, the Columbian “doctrine of discovery,” and the European master narrative of progress, including his willingness to consider his own complicities with the oppressive colonial practices he otherwise denounces. Ultimately, I will argue, Head’s Argentine writings demonstrate a self-reflexive critical promise that he failed to enact during his subsequent tenure as lieutenant-governor of Upper Canada.