Rhetorical judgment is a syncretic term that marries the classical concepts of prudence and rhetoric, and suggests their mutual interdependence. The traditions of rhetoric and prudence have had uneven histories, their legitimacy and utility ebbing and flowing within the dominant strains of Western culture. There are four key moments in histories to help find their points of contact, their disjunctions, and their fickle alliance. The key points of tension in their collaboration occur, first, within the Aristotelian corpus itself, next between Greek and Roman conceptions of social reason, then between the ancient and early modern conceptions of prudence, and finally in the fitful return of interest in both of these classical approaches to social reason in late modernity. Their alliance is actuated most potently when the inherently social dynamism of rhetoric transforms prudence from a virtue into a practice. The capacity for prudence to trade in the contingent circumstance then becomes a powerful political resource. Rhetorical judgment is now realizing this potential as critical theory engages it to redefine the terrain of the political, and to reimagine the contours of a seemingly antiquated body of traditions. The dimensions of power, contingency, and expedience that have always had a place within rhetorical and prudential practices are now finding radical new forms of expression and pointing toward new conceptions of democratic practice.