This chapter examines the libertarian and reactionary elements in William Burroughs’ life and work, placing them in dialogue with the twenty-first-century alt-right’s attempts to reclaim him as a prophetic figure. Florian Zappe interrogates the paradox of Burroughs as both icon of the countercultural avant-garde and a card-carrying NRA member who espoused conspiratorial, anti-statist, and sometimes openly bigoted views. The chapter traces how alt-right figures – from internet provocateurs to fringe ideologues – have co-opted Burroughs’ anti-establishment ethos and aesthetic of transgression, often through decontextualized misreadings that ignore his literary complexity and formal irony. Zappe explores Burroughs’ ambivalence toward political systems, his rejection of ideological coherence, and his commitment to aesthetic resistance rather than activism. Ultimately, the chapter argues that while Burroughs’ work harbors troubling reactionary tropes, it defies fascist instrumentalization by resisting ideological fixity and embracing an anarchic pluralism that places him far outside the alt-right’s monolithic vision of power.