Pragmatism as a theoretical enterprise has been criticized since its inception for not having a coherent account of the role of power and violence in human affairs as well as a moral justification and criteria for marshaling arguments in favor of democracy. In this essay I approach recent developments in pragmatic democratic theory with those persistent criticisms in mind. Rather than lacking justificatory resources and underthematizing the role of violence and asymmetrical power relations, Robert Talisse’s and James Bohman’s works, respectively, demonstrate the epistemological depth and power of updating pragmatism as a theory of situated and critical political inquiry. However, each could be extended by utilizing a more robust description of the problematic situation polities currently face. Specifically, I turn to Dewey for guidance in how our pragmatic epistemological and evaluative practices might incorporate the facts of our problematic situation. I do this in terms of the power structures of economic processes both in terms of contract and in terms of the intellectual discourses that attempt to scientifically describe these processes.