In this chapter, I contend that Shakespeare’s Measure for Measure provides a brilliant case study in the entangled vicissitudes of character and state sovereignty. From the hyper-moral and hyper-legalistic rigidity of Angelo, the Duke’s substitute sovereign, to the bawdy irreverence of Lucio, the Duke’s trickster double, to the indomitable life force of imprisoned Barnardine—divergent microclimates are breaking out all over town, emanating from one character to the next. Which will rule the other? Measure invites us to try on and assess different political and personal identities. In what emotional bandwidth, in the name of what character ideal, shall we participate in social and political discourse and action, and with what individual and collective consequences? Do we like who we become? Might we choose to forge a different personal and collective reality? Everything depends on how the properties of government unfold: by whose agency, in what preferred (or imposed) register? In this way, Measure dramatizes freedom’s promise in the development of self and political governance against the backdrop of its Machiavellian shadow. It is a remarkably prescient lesson in the overlapping vicissitudes and responsibilities of a liberal democratic politics to come.