How many years did it take Chaucer to rise from servant to trusted diplomat?

During the decade of the 1370s, Chaucer was at various times on diplomatic missions in Flanders, France, and Italy. Probably his first Italian journey (December 1372 to May 1373) was for negotiations with the Genoese concerning an English port for their commerce, and with the Florentines concerning loans for Edward III. His next Italian journey occupied May 28 to September 19, 1378, when he was a member of a mission to Milan concerning military matters. Several times during the 1370s, Chaucer and his wife received generous monetary grants from the king and from John of Gaunt. On May 10, 1374, he obtained rent-free a dwelling above Aldgate, in London, and on June 8 of that year he was appointed comptroller of the customs and subsidy of wools, skins, and tanned hides for the Port of London. Now, for the first time, Chaucer had a position away from the court, and he and his wife had a home of their own, about a 10-minute walk from his office. In 1375 he was granted two wardships, which paid well, and in 1376 he received a sizable sum from a fine. When Richard II became king in June 1377, he confirmed Chaucer’s comptrollership and, later, the annuities granted by Edward III to both Geoffrey and Philippa. Certainly during the 1370s fortune smiled upon the Chaucers.

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