This chapter reintroduces Niccolò Machiavelli not as a mere theorist of power but as a remarkably skilled diplomat navigating stark power asymmetries. Serving a militarily weak Florence, Machiavelli negotiated repeatedly with Europe’s “giants”, the kings of France, the Emperor of the Holy Roman Empire, and the formidable Cesare Borgia, while also grappling with the constraints imposed by his own principals at home. Far from the caricature of a scheming opportunist, Machiavelli emerges here as a practitioner whose dispatches and reports highlight the crucial interplay between negotiation “at the table” with powerful counterparts and “behind the table” with skeptical leaders. The analysis draws on Machiavelli’s early diplomatic missions and his later theoretical writings, including his advice to fellow ambassadors. It outlines key lessons from rigorous information-gathering and alliance-building to adapting language and style to one’s interlocutor. Machiavelli’s insistence on creating “durable alliances,” building a credible military alternative, and skillfully managing internal alignment underscores the enduring relevance of his counsel. Ultimately, this study reframes Machiavelli as an agent of responsible statecraft, offering timeless insights on how a “pigmy” can effectively negotiate with “giants.”