In this chapter, we see how Cicero, as a rising Roman politician, uncovers hidden lines of influence, pinpoints shades of political support, and frames partisan divides in the Roman Republic. Here, Cicero uses voluntas both to analyze politics as he finds it and to argue for its rational improvement. Descriptively, Cicero uses voluntate and summa voluntate to identify subtler shades of opposition or support and to trace lines of unseen influence among Rome’s leading men like Pompey and Caesar. Through his gifted pen, will becomes a measurable force as it had seemingly not been before. To measure will is to rationalize it, and Cicero builds new philosophical arguments for the primacy of voluntas over violence and for a vision of politics that transacts power rationally by the intersecting wills of magistrates and people. I use powermapping, a tool of modern advocacy, as a lens to examine Cicero’s political strategy and use of language. This vision, at once old and new, is upended by the ascent of Caesar, whose sole voluntas undoes Cicero’s rational framework, exerting will by brute force and eliminating the old pluralist order.