This chapter examines Milton’s discourses of liberty, slavery, and hierarchy in order to test Quentin Skinner’s claim that the theory of neo-Roman liberty is positively and intrinsically connected with equality. Neo-Roman liberty was an important element in Milton’s political arguments, as was the terminology of slavery which was used to encapsulate the absence of that freedom from domination. However, neo-Roman liberty for Milton is less aptly defined as freedom from the will of another than as freedom from arbitrary domination. Milton’s commitment to the existence of rightful hierarchies, and to the Aristotelian principle that the superior should rule the inferior, meant that many (whether wives, servants, actual slaves, or inferior or wicked citizens) could not appeal to the principle of neo-Roman liberty to free them from subjection to another, as that subjection was rightful rather than arbitrary. Milton’s emphasis on free will and virtue meant that expected hierarchies might be disrupted by exceptional virtue or vice, but these exceptions caused a certain dissonance in Milton’s texts, and his use of the language of slavery and subjection was not entirely consistent.