The starting point of this essay is an exploration of Andrea Caffi’s intellectual formation, highlighting the influence of Russian Populism. To this influence are traced back his initial aversion to political vanguardism, as well as his strong belief in radical-federalism that drove him into a wide polemic, both strategic and theoretical, with the anti-fascist movement Giustizia e Libertà. The essay then presents Caffi’s concept of sociability, significantly indebted to Simmel’s sociology. The theme of retroguardie culturali (loosely translated as Cultural Rearguards) thus unfolds in its theoretical premises – the idea that anthropologically speaking, sociability represents the inherent resource of the human condition as the alternative to the will of power – ultimately emphasizing the urgency of their political-pedagogical action.