The article provides a critical analysis of the pluralist socialist visions of G.D.H. Cole and H.J. Laski, developed during and after World War I. Both thinkers sought liberation from the social consequences of capitalism through democratization of civil society. Whereas Cole’s pluralism found expression in the vision of a stateless federative system of complementary associations, Laski formulated a functional theory of rights based on the idea of the state as the overall coordinator of civil society. They both celebrated the individual as infinitely creative and irreducible to the associations to which it belongs. The article focuses on the relationship between functionalism and freedom in their works and argues that even if both aspects are brilliantly developed, an unresolvable tension remains.