This chapter explores William Burroughs’ complex role as a prophetic figure in American literature, tracing how he simultaneously embraces and subverts this identity. Drawing upon Puritan and Romantic traditions of the poet-prophet, the chapter situates Burroughs alongside figures like Walt Whitman, yet distinguishes him through his irreverent and often satirical stance. Burroughs’ prophetic persona was partly constructed by contemporaries such as Allen Ginsberg and Jack Kerouac and is shaped by his fascination with Hassan Sabbah, a mystical figure whose image he reclaims in opposition to American control systems. The chapter examines how Burroughs’ predictions – ranging from pandemics to terrorism – reflect both visionary insight and societal anxieties. Furthermore, his cut-up technique, developed with Brion Gysin, is interpreted as a form of literary sorcery akin to cleromancy, blending satire with shamanic prophecy. Ultimately, Burroughs emerges as a prophet who deconstructs prophecy, offering a self-aware critique of authority, language, and cultural mythmaking.