This essay examines the creation of a notorious anecdote about a Machiavellian mother — Caterina Sforza. The adjective "Machiavellian "functions on two levels: first, Sforza often simply appears in her role as mother in Machiavelli's works; second, her behavior in this particular instance might well be characterized as "practising duplicity in state craft. " Yet if one considers the pertinent historical documents and Machiavelli's very first, although virtually forgotten, version of the events, it becomes apparent that Machiavelli "de-Machiavellizes" Caterina Sforza. The historical record offers a narrative in which Sforza provides a localized, targeted political response to undermine her children's would-be assassins. Machiavelli, however, rewrites the episode by altering Sforza's quip to her enemies and adding the audacious gesture of lifting her skirts; as a result, he creates a version in which she no longer responds to the political predicament in which she finds herself. This essay juxtaposes Machiavelli's long-ignored first version of the tale with his other two more well-known prose versions and contextualizes all three in relation to contemporary sources.