During peace negotiations in 1360, a twenty-year-old Chaucer carried official letters from England to Calais. He would continue with a career of representing the English crown all across Europe. A close relationship existed between the wealthy mercantile class and royalty. It is not difficult to imagine that an energetic, young emissary would be well-treated, catered to, in luxurious households and foreign courts wishing to gain favor with the English. And consider that there would be an advantage for Chaucer in not being of noble birth: He could comfortably mingle with foreign servants and tradesmen. He'd get the whole picture.
We first see an entry denoting "safe conduct." Chaucer made an official visit in 1366 to the King of Navarre, probably regarding the threat of an invasion by his neighbor, Pedro of Castile.
A few years later, in the on-again-off-again Hundred Years War, he served with John of Gaunt's forces in France.
In 1371, he set out for the coastal town of Dartmouth to settle a touchy matter involving a ship owned by a Genoese. Subsequently, he had a "warrant to negotiate" with merchants of Genoa to construct a dedicated seaport for them in England.
Soon after, he made a winter journey with two high-ranking Genoese, their servants and bodyguards. It makes me shudder to picture the hazards from both weather and terrain in crossing the Alps in December. His many dealings with Italians make it a safe assumption that he had a fluent acquaintance with their language.
His competence as a diplomat is attested to when given the delicate mission to Florence of facilitating a loan. The delicacy had to do with Edward's having defaulted on the banker's previous loan.
In 1377, within the space of a few months, he completed four missions to France. One led to Paris. The other destinations are unknown. Following that, he traveled to Lombardy on a long assignment about the ever present topic of "war" and a search for reliable allies.
In what must have been an especially demanding undertaking, he accompanied six officials with bodyguards to talk business with Barnabo Visconti, known as the "cruel tyrant of Milan." Barnabo possessed massive wealth; and his son-in-law could muster countless mercenaries. Barnabo also had a daughter, Caterina, he hoped to align with the English crown.
Chaucer had been valued as a diplomat and government official, not as a poet. Even his very responsible position as Controller of Customs in London did not rank in importance with his diplomatic reputation. A "deputy" served in his place when he traveled for the king.
An entry recorded in 1387 shows an apparently small assignment for him to Calais. That destination brings Chaucer full circle, concluding his service as ambassador (for both Edward III and Richard II) of more than twenty years, where it had begun.
He had been trusted to negotiate in matters of war, money, marriage, and commerce. Next, we will add more details to our image of Chaucer the poet.