Research in recent decades has drawn out the Caribbean dimensions and occlusions of the Harlem Renaissance and its historiography. Building on the foundations of such work, this chapter focuses on a rarely discussed Caribbean backstory to a symposium on Negro art that W. E. B. Du Bois ran in The Crisis through much of 1926. As a backdrop to US-tropical American fissures, the discussion charts some of the graphic, textual, and representative tensions between Alain Locke’s Survey Graphic, “Harlem: Mecca of the New Negro” and The New Negro anthology and rival work by Eric Walrond and Miguel Covarrubias in Vanity Fair. In the foreground, it examines how Knopf’s 1925 edition of Haldane Macfall’s 1898 novel, The Wooings of Jezebel Pettyfer – which is virtually unheard of today – prompted one of the most significant discussions on the issue of black representation in the arts in the 1920s.