This chapter examines the role that race and ethnicity play in the works of David Foster Wallace. More specifically, I am interested in what I identify as a key contradiction in the writer’s bibliography: how his hyper-attentiveness to the ways in which late capitalism inundates contemporary life fails to account for how that same late capitalist logic simultaneously acts to racialize and subjugate communities of color. Through readings that span the author’s career – from Signifying Rappers and “Authority and American Usage” to Infinite Jest and The Pale King – I explore how Wallace finds himself unable to openly navigate questions of race and discrimination and by so doing reproduces late capitalism’s project to buttress dominant ideology while outwardly projecting a self-conscious, anti-racist rhetoric. Ultimately, I deem Wallace’s inability to account for race in his critique of hyper-consumerism as symptomatic of a larger critical tendency to overlook racism’s inextricable connection to capitalism (what Cedric Robinson terms as racial capitalism).