This chapter reads Colson Whitehead’s novel The Underground Railroad as a Janus-faced text in American literary history that looks back toward the persistent political conundrums illuminated by twentieth-century American fiction and reconfigures them in generative ways for the twenty-first century. Like earlier twentieth-century neo-slave narratives by Ishmael Reed, Octavia E. Butler, and Toni Morrison, Whitehead’s novel critiques a naïve historical story of inevitable Black progress, and it even flirts with the notion that American democracy and African American oppression are inextricable. But Whitehead rejects fatalistic narratives of inevitable injustice by showing how American normative myths can still be politically efficacious. Establishing himself as a key literary figure in contemporary Black political thought, Whitehead uses the speculative fiction genre to transform celebrated concepts in American political theory – e.g., individual freedom, legal equality, constitutional rights, representative democracy, popular sovereignty – by contextualizing them within Black experiences across time. Ultimately, his political vision amounts to a wary optimism, which Whitehead himself has called a politics of “impossible hope.”