Drawing on archives from the US labour movement, personal papers of transnational labour organisers, Bolivian oral histories and press reports, and government records from four countries, this article explores a web of Cold War relationships forged between Bolivian workers and US government and labour officials. Uncovering a panoply of parallel and sometimes conflicting state-supported trade union development programmes, the article reveals governments’ inability to fully control the exuberance of ideologically-motivated labour activists. Rather than succeed in shoring up a civilian government as intended, US President John F. Kennedy's union-busting programme aggravated fissures in Bolivia's non-Communist Left, ultimately frustrating its attempt to steer a non-aligned posture in Latin America's Cold War. Employing transnational methods to bridge gaps between labour, development and diplomatic history, this article points toward a new imperial studies approach to the multi-sited conflicts that shaped the post-war trajectory of labour movements in Bolivia and throughout the Third World.