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This essay examines two historical documents—David Walker’s Appeal to the Coloured Citizens of the World and Martin R. Delany’s The Condition, Elevation, and Destiny of the Colored People published in 1929 and 1952, respectively—to stress the rhetorical astuteness of African-Americans writing from the margins in hostile antebellum America. The essay argues that, rhetorically these documents expose America’s weaknesses and contradictions between the principles of freedom that motivated the country’s founding fathers and the compromises that recognised and permitted the continuation of slavery. Specifically, these rhetoricians exploit and subvert Thomas Jefferson’s paradoxical, if not conflicting, thesis on the status of African-Americans in America to advance their argument. We hold these truths to be self-evident, that all men are created equal, that they are endowed by their Creator with certain unalienable Rights that among these are Life, Liberty, and the Pursuit of Happiness.