This work entails a constructive critique of communicative planning theory in the light of a serious lacuna in planning theory. This lacuna is the near complete absence of the historical experience of third world leftist democratic experiments as a contextual base for the generation of mainstream planning theories. This work studies the experience of one such experiment - the decentralisation and democratisation of the planning structure in the city of Kolkata and the state of West Bengal, of which it is the capital, undertaken by the former Left Front government - to expand the contextual base of communicative planning theory. It has been argued that leftist democratisation experiments such as the one undertaken in Kolkata derived no inspiration or theoretical guidance from communicative planning theory. The experience of Kolkata shows that a democratic and communicative planning structure can evolve out of strategies that are opposed to the communicative ethic - a combination of parliamentary and extra-parliamentary politics geared towards open class confrontation.