This paper provides a feminist critique of theories of liberty in two of Thomas Middleton’s city tragedies. Expanding on the neo-Roman theories of liberty presented by Quentin Skinner in Liberty Before Liberalism, I connect Middleton’s city tragedies to feminist critiques from Mary Nyquist and Ellen Mieksins Wood. Close readings of Women Beware Women and The Revenger’s Tragedy reveal connections between Middleton’s radical critiques of tyranny in later theories of liberty of the English Civil War. Because Middleton’s critiques are explored through both the state and marriage relations, I argue that Middleton exposes the same contradictions of liberty in the institution of the family, providing insight into notions of slavery, servitude, and coercion under the public rule of the sovereign and in the privacy of the home. Reading such contradictions back through Middleton, can, I argue, allow for a better understanding of feminist critiques of such theories of liberty.