The essay traces Bruno Trentin’s political biography and intellectual research from a transnational perspective. Through his work notebooks (1953–1995), diaries concerning the general secretariat of the CGIL (1988–1994), his work in the European Parliament (1999–2004), and his theoretical reflections over the following two years, the birth of “Freedom Comes First” (2005) is rooted in a long-standing critique of the subordination of communist and social-democratic culture to the Fordist model, in the name of a libertarian socialism based on the centrality of the individual and the relationship between work and knowledge. What emerges is the originality of Trentin's political thought, the transnational intellectual circuit in which his research developed, and his vision of a federal Europe in the post-Cold War international system, until the failure of the European Constitution project in 2007.