Chapter 3 analyzes freedom as doing “whatever one wishes” in fourth-century oratory. As several scholars have noted, doing “whatever one wishes” appears ambivalent in forensic speeches. They argue that, since Athens was not an anarchic state, extreme freedom could be glossed as a threat to sociopolitical stability. In contrast to prevailing scholarship, however, I argue that the most dominant principle, even in these texts, is the preservation of positive freedom as justification for the litigant’s position. While acting “however one wishes” may be presented as objectionable, the rhetoric of that assessment emphasizes who is doing “whatever they wish” and whom they affect by doing so. Bad characters, whether a criminals, oligarchs, or metics, can be rebuked as undeserving of positive freedom and abusing the power that attends it. The limitation of another citizen’s ability to do what he wishes can also condemn the action. Doing “what one wishes” is not a byword for antidemocratic action, but can have such a connotation because of the particular actors or victims of the actions. It is the misuse of the natural qualities of a citizen that leads to censure.