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In recent years several public commentators have suggested that we are at the beginning of an era of political shamelessness in Western democracies. Lack of a sense of shame has been used to characterize the political behavior, statements, and actions of a number of leaders, who have broken with what are considered socially accepted norms of public and private behavior. Yet, accusations of shamelessness raise a set of complicated questions, such as the difference between shamelessness and anti-conformism or the social and cultural role played by shame in disciplining dissident behavior. In this paper I will turn to Plato’s treatment of political shamelessness in the Protagoras, Gorgias and Republic, in order to reframe the critique of the shamelessness of contemporary leaders as pointing to the corrosive effects that imperviousness to the emotion of shame altogether or the loss of the capacity to feel shame have on social bonds. I will especially focus on Plato’s critique of the shamelessness associated with a certain style of political democratic leadership and with tyranny, in order to show that this critique is not based on a conservative attachment to established social norms, but on a sophisticated understanding of the connection between inability to feel shame and inability to share in a society with others.