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Historians have studied many different kinds of diplomatic agents: particularly ambassadors, nuncios, and proctors. Here we would like to offer some first reflections on the Florentine commissioner-orator (commissarius seu orator), whose role interlaced the strategies of foreign politics with the needs of protection of the domain under the Republic’s jurisdiction. Using both unpublished and published sources, we will draw here the previously unexplored profile of this amphibious office. We will focus on its functions of representation, information and negotiation, as well as its diplomatic features and its active role in conflict management. Among the answers to the causae urgentissimae which regularly stimulated the diplomatic engineering of the Florentine Republic, the commissarii seu oratores allowed the management of dangers at boundaries and the need of negotiations with captains and condottieri at Florence’s service, as well as with enemies of the Republic.