Fifty years after its publication and one year after Bobbio’s death, the new edition of his well known Politica e cultura provides scope for a renewed reflection about a challenging issue that was a constant throughout the philosopher’s research: the relationship between intellectuals and society and, as a consequence, the complex connection between intellectuals and political power. Three crucial points are tackled by Bobbio in particular in this work, also in the light of the issues that are currently in the spotlight of sociological, theoretical and political discussion: dialogue, the theorisation of freedom and the function of the intellectual. A close look at the articulation of his argumentations reveals the peculiar conception of democracy and organisation of society deriving from the labyrinth of his research. Considering Bobbio’s way of dealing with these issues whose theoretical (and practical) benchmark is that of the intellectual mediator an interpretation that also takes the subsequent development of his thought into consideration reveals a tension between the idea of the intellectual who does not want to be entangled by cultural politics (thus becoming organic) and the political enthusiasm that leads thoughts to settle into precise statements, whether political or not. This tension is in any case strictly related to the philosopher’s constant attention not only to his authors, but also to his masters and comrades.