This paper presents an overview of Alessandro Fontana’s research on Machiavelli, the Venetian ambassadors and the birth of a new political practice and thought in Renaissance Italy. To this end, it deals with Fontana’s analyses of the couples virtue/fortune and security/power in Machiavelli, and with his investigations into the nature and characteristics of the Venetian relazioni. The conclusion emphasises Fontana’s notion of historical consciousness and his reference to Benedetto Croce in the illustration of his historical method.