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Kenneth Warren suggests in his book, What Was African American Literature that what separates literature today from what proceeded, is that it is retrospective in nature compared to the prospective literature of our past that fought against narratives of black inferiority. Colson Whitehead’s retrospective examination of America’s history of slavery in his contemporary novel, The Underground Railroad, exposes some of the limits of Warren’s argument, particularly his ideas about periodization. Through close readings of the novel and drawing from Derrida’s theory of the metaphysics of presence, I aim to show how Whitehead challenges and questions a fixed state of possibility or freedom from slavery in America. I suggest that through Whitehead’s actualization of the Underground Railroad combined with the theory of the metaphysics of presence, Whitehead challenges and questions a fixed state of possibility or freedom in America, but instead suggests that freedom works like a transcendental signified. My paper explores how Whitehead’s novel draws from the African American literary tradition of the slave narrative and his use various literary techniques allows him to blend histories of America and slavery with images of a contemporary nation state that coalesces into a thoughtful and compelling neo-slave narrative that blends history, narrative, and our contemporary moment into one. Moreover, Whitehead’s novel creates a presentism and counter-historicism through the neo-slave narrative genre that enables him to engage in critical and contemporary debates of race and literary theory.