"Wayward Poets" examines the long careers of Walt Whitman, Herman Melville, and Frederick Douglass. Although these authors are typically associated with certain mid-century texts (i.e., the 1855 Leaves of Grass, Moby-Dick, and The Narrative of the Life of Frederick Douglass), their careers in fact span the arc of the nineteenth century. Across this period, they experiment with a variety of literary forms - from journalism to fiction, public speaking, and literary criticism - but are each drawn, at particular moments and for particular reasons, to poetry. This interest in verse, I argue, has to do with its relationship to time, and with these writers' broader entanglements with temporality as a medium of political experience. Indeed, I bring these figures together, ultimately, to reveal a shared formal project, insofar as they each manipulate poetic structures in order to reimagine the shape and propensities of historical time. Assembled through internal splits, ruptures, and inversions, theirs is a fractured verse, and these formal breaks are directly tied to questions about how, and to what ends, a people can share a polity. Chapters 1 and 2 consider the ways in which temporality acquires political meaning and formal significance in Whitman's poetry. Comparing Leaves of Grass across its many editions, I argue that Whitman's book is structured through a slow but definitive move away from the early verse's now-time in favor of a teleological not-yet. I examine the ways in which this transition from a poetics of immediacy to a poetics of anticipation is connected to Whitman's reading of Hegel; to changes within liberal ideology; and to the postbellum struggles of American workers. I move from Whitman's chants to Melville's poetics in chapters 3 and 4, which look at how Battle-Pieces and Clarel provide an immanent account, or inside narrative, of Melville's transition from novelist to poet. Through the Civil War, Melville comes to perceive history as a process of destructive repetition, and this altered historical sensibility plays a pivotal role in his embrace and use of verse. In both Battle-Pieces and Clarel, he crafts a poetry in which damaged rhymes, broken meters, and twisted syntax attempt to carry the weight of the war as a historical phenomenon and connect the conflict to other episodes of discontinuity. Chapters 5 and 6 recast Frederick Douglass as a political poet. Douglass's orations, wherein most of his poetry arises, create fissures and pockets in time by constructing patterns of temporal relation that divorce listeners and readers from official modes of remembrance. It is in these temporal breaks that Douglass's poetry erupts, often through quoted - and then strategically revised - lines of verse, in order to promote emancipatory forms of feeling and connection. From his repeated use of Byron's The Giaour in his Civil War speeches to his enlistment of William Cowper's The Task to describe slave song in his autobiographies, Douglass invokes verse to activate a unique mode of experience vital to fashioning counter-publics against slavery.