Over the past half-century, Noam Chomsky has established a powerful intellectual presence in two apparently unrelated domains of discourse — the field of theoretical linguistics and the arena of anti-establishment politics. This paper examines Chomsky’s use of metaphor across these domains, arguing that in Chomsky’s work metaphor enables an undercover, perhaps even classically ‘anarchic’ dialogue between disciplines. Organizationally as well as psychologically, the two major inquiries into human nature undertaken by him are, the paper suggests, structured and unified in relation to each other via the seemingly innocuous agency of metaphor. The paper also traces Chomsky’s innovative production of metaphors to engage in dialogue with both the past and the future. To reconstruct Chomsky through his metaphors is to attempt to read him not as a doctrinaire Cartesian but as someone who has responded with extreme ‘context-sensitivity’ to changing circumstances in both his fields. Finally, the paper contends that a study of Chomsky’s metaphorical practice could, inter alia, offer unprecedented insights into the creative and essentially unified thought processes of a major 20th century thinker.