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Throughout US history, the value of freedom has incited democratic revolution, slave emancipation, and social justice movements, but it has also incited imperialism, war, slavery, racial and gender oppression, indigenous appropriation, and the violent machinations of a ‘free’ market. I argue not just that freedom takes shape as oppression, but that commonplace notions of universal freedom and individual personhood can depend upon and sustain forced labor, resource depletion, patriarchy, land theft, and hierarchical systems of racism and civilization. In this paper, I call these freedoms Ugly Freedoms. By using the term ugly to describe these forms of freedom I draw from and extend ugliness as an aesthetic category of interpretation to suggest, at one level, that these freedoms invoke displeasure, disproportionality, or repulsion. Ugliness as an aesthetic category is a system of taste that deems objects or practices degraded, deformed, or repugnant. It attaches ugliness to things with subjectively-determined offensive properties that work in multiple sensory registers of vision, smell, and taste, to generate a felt experience of displeasure. But I will draw on these aesthetic categories in a political way by examining how practices and discourses of freedom provoke sensorial responses of repulsion, violence, and oppression, connected to political and economic effects of brutal power.