In the Mediterranean of the second half of the sixteenth century, among dragomans, prisoners of war, and unscrupulous spies, moved a man capable of serving multiple masters and changing sides several times during his brief but fascinating life - his name was Bartolomeo Bruti, perhaps the most enigmatic among the secret agents of the era. Originally from the Albanian city of Ulcinj (called Dulcigno by the Venetians), which fell under Ottoman control in 1571 - a clash in which Bartolomeo's father, Antonio, had lost his life - Bruti began his diplomatic career as a dragoman in service of the Venetian bailo in Constantinople. But soon his activity went well beyond translation: in 1575 he participated in a prisoner exchange between Spain and the Ottoman Empire, an event that allowed him to travel freely and gather vital information; as already recounted in another story, prisoner exchanges were golden opportunities for intelligence operations. It was precisely in this context that, according to historian Noel Malcolm, Bruti switched sides, offering his services directly to the King of Spain, Philip II. He thus became part of the network built by Giovanni Margliani, the head of mission of the nascent Spanish secret service in the Levant and who would have a crucial role in Spanish espionage in Constantinople. A double or perhaps triple agent, Bruti acted with constant ambiguity, navigating between religious identities, temporary alliances, and divergent political objectives. After a life that took him into the most unexplored depths of Balkan Europe, Bruti was killed in the voivodeship of Moldavia, a long affair that would merit more exhaustive treatment. However, what is worth emphasizing is that Bruti's story represents a perfect example of what we would today call "transconfessional diplomacy," made not only of ambassadors and treaties, but also of men without flags, ready for anything in order to obtain personal advantages or support a cause - when not both. In the world of Renaissance embassies and chancelleries, Bruti is living proof that the boundary between spy and diplomat was not only tenuous: it did not exist.