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Merleau-Ponty’s thought has rarely been brought into relation with Greek thought, and even less so with the foremost political actors who spoke in Athens before the assembled people, and whose speeches have been passed down to us. A comparative approach to Demosthenes’ political speeches and some of Merleau-Ponty’s texts on specific topics such as freedom, adversity, engagement, expression, or encroachment will fuel a constructive dialogue between these two styles of investment of the political space—direct and indirect—so as to renew, at least in part, through this very exchange, the understanding we may have of the political stances taken by these two authors. In this paper, we will draw a number of ethical conclusions from this dialogue, notably through the study of the concept of engagement, which constitutes one of the richest points of contact between the two authors. The analyses of adversity, courage, and of engagement as a mode of expression of political freedom will lead us to sketch guidelines for an ethics of open expression—notably through the gaze and the shame that is potentially coextensive to it—which finds its foundation in an axiological reorientation of the meaning suggested by reality to one and all.