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The 500th anniversary of The Prince (1513) provides a timely opportunity to explore Machiavelli’s concept of negotiation, as it appears in his works, written following several diplomatic missions. While clearly obsessed by the necessity of a stable political order, and by force in its extreme manifestation—war—Machiavelli does not consider negotiation as secondary. Negotiation becomes an important tool for the Prince, through his ambassadors, for which Machiavelli wrote several diplomatic instructions. In his dispatches, negotiation appears to be dominated by a concern for secrecy and dissimulation.