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Adorno and Levinas argue from distinct yet intersecting perspectives that there are pathological forms of freedom, formed by systems of power and economic exchange, which legitimate the neglect, exploitation and domination of others. In this paper, I examine how the works of Adorno and Levinas assist in diagnosing the aporias of liberty in contemporary capitalist societies by providing critical models and strategies for confronting present discourses and systems of freedom that perpetuate unfreedom such as those ideologically expressed in possessive individualist and libertarian conceptions of freedom.