This PhD thesis explores the role of sympathy in the discursive formation of race in Scottish and American eighteenth- and nineteenth-century literature. Offering insight into Adam Smith’s Theory of Moral Sentiments as one paradigm that underpins the philosophical terms of sympathy in the Atlantic world, I argue that sympathy as a mode of control and a mechanism of normalisation played a formative role in the transatlantic history of the literary construction of whiteness. My introductory chapter delineates key debates on sentimental literature and argues that race in general and whiteness in particular have been ignored in revisionist accounts of the genre. My second chapter outlines Smith’s concept of sympathy in the context of Scottish Enlightenment theories of stadial history, suggesting that sympathy is always already bound up with a racial understanding of others in a categorical system of cultural development. I examine this dialectic of race and sympathy in the novels of Henry Mackenzie, which present social inequality, colonial exploitation, and slavery as conditions that the sentimental genre cannot rectify. This discussion is continued in chapter three, which deconstructs Harriet Beecher Stowe’s sentimental rhetoric in Uncle Tom’s Cabin, suggesting that while it is employed to foster fellow-feeling for the black slave, it also reduces others to the terms of the white self. Chapter four demonstrates that Uncle Tom’s Cabin’s philosophy of white sympathy is fully articulated in Stowe’s New York novels, My Wife and I and We and Our Neighbors, as a discourse of affinity, which functions as an advertisement for white bourgeois homogeneity in a developing consumer culture. The concluding chapter explores sympathy in relation to race passing and scientific racism in Jessie Redmon Fauset’s Comedy: American Style, where the passing protagonist embodies the gaze of sympathy that cares for others according to their degree of whiteness. Fauset, I argue, critiques the legacy of nineteenth-century sentimental literature, just as she, along with Du Bois and others, opposes eugenicists’ vision of a ‘White Atlantic’ as a new world order.