What happens if reading a tradition that is implicated in violence against you is essential for understanding yourself and your place in the world? What new perspectives on classical antiquity, and on what classical antiquity can mean for us today, could this ambivalent way of reading offer—if we read the classics as destructive but also generative, as damaging but also, ultimately, necessary? W. E. B. Du Bois, a Black American writer, sociologist, and civil rights activist, and Hannah Arendt, a German Jewish refugee, essayist, and political theorist, allow us to answer these questions. I focus on texts in which Du Bois and Arendt explore the perspective of the outsider, the other or the outcast, on cultural monuments. In doing so, they sketch a theory of tradition in which the figure of the self-conscious outsider plays an essential role. This figure, whom Du Bois associates with double consciousness and Arendt names the “pariah,” becomes in their readings 1) a privileged reader or viewer of cultural monuments which are imagined to be exclusive and 2) an essential participant in sustaining and innovating on the tradition to which those monuments belong. This talk derives from my current book project which explores the complex triangulation between Black Americans, German Jews, and Greco-Roman antiquity through Du Bois’s and Arendt’s writing and the powerful but ambivalent relationship they each had with the classics.