This essay examines for the first time the poetry of Henry St John, Lord Bolingbroke. Although Bolingbroke is now best known as a political theorist, historical writer, and opposition propagandist, he started his career as a poet. He published widely during the latter part of the reign of William III and his poems circulated in manuscript. Bolingbroke’s poems, this essay contends, illuminate the ideological consistency of his early career. An introductory section documents Bolingbroke’s involvement with John Dryden during the 1690s, and a second section then charts his collaborations with other members of Dryden’s circle and unpacks the cultural politics of their poetry. The essay then explores the intertextuality of Bolingbroke’s poems and the implications on the poet’s intellectual milieu. The final sections of the essay investigate Bolingbroke’s literary patronage during his tenure as a minister of state, before documenting the influence of Bolingbroke’s early oppositional rhetoric through his later campaign against Sir Robert Walpole.