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The article examines the ritual meaning of the “freak” bet of the late nineteenth century, primarily as this took place in the city of Philadelphia. I propose that an election ritual can be thought of as an embodiment of the so-called “democratic paradox” put forward by Chantal Mouffe. The tension of the ritual lies in the question of whether it is able to satisfy competing demands on the modern polity and the citizens who compose it. I argue that the freak bet was an attempt to “think through,” or publicly communicate, some of the paradoxes of modern liberty. It did not succeed in providing a definitive answer, since, as I suggest at the end, it is in the nature of liberal democracy that such an answer will not be forthcoming.