This article explores the symbolic appeal of Che Guevara within radical Left circles of the 1960s and 1970s. Che's importance as a shared political reference offers a unique window on aspirational symbols and the desire for meaningful transnational solidarity. By tracing Che's resonance in Latin America, western Europe, the United States, and the Middle East, the article brings into conversation the study of post-war radicalism, political iconography, and the cognitive dimensions of interconnectivity. As a means of understanding Che's appeal to both protest movements and guerrilla organizations, the article develops the notion of a ‘transnational imagination’, or mode of perception that frames local circumstances in a world historical trajectory and thereby affects collective aspirations and actions.