This multidisciplinary pedagogy offers eight allegorical images in support of a visually contextual reading of The Prince. Responding to the pedagogical problem of students treating the text as an ahistorical manual for action addressed to them, our approach resituates The Prince in its visual cultural context. This allows us to specify Machiavelli’s innovations as a theorist in terms of the importance of plurality and particularity in regard to political action. An online supplemental appendix provides access to databases and additional resources. Exploring Machiavelli’s politicized moral concepts of prudence, parsimony, liberality, fortune, and impetuosity using these images, we show his masterful invocation and redeployment of the cultural codes of his time. In presenting a visual history of concepts, we hope to move students beyond common contemporary ideological biases and literal readings and to alert them to the complex stories and relationships evident in the visual history of civic humanism.