Adam McKible makes a strong case for attending to popular white writers of the 1920s who used fiction to give ballast to Jim Crow. Analysis of Octavus Roy Cohen’s work in the Saturday Evening Post demonstrates how Harlem Renaissance writers were positioning their work against white popular fiction that threatened to obscure the realities of African American lives and history behind a continuous stream of invective, disdain, and ridicule. Cohen created a new mode of popular fiction that combined sustained engagement with modernity and technology with familiar tropes from minstrelsy. The chapter reads Cohen’s representation of globetrotting black characters in dialogue with Harlem Renaissance writers’ deployment of the motif of shadows to explore both the realities and representational strategies of segregation and the shadow of imperialism. In doing so, it complicates a tendency to equate transnationalism and diasporic identities with radicalism, noting that Cohen repurposed representations of Black modernity and travel for white supremacist ends.