Many know Geoffrey Chaucer as the famous Middle English poet who wrote The Canterbury Tales. But did you know that Chaucer’s life could still be considered extraordinary even if he never wrote that poem? Indeed, he went to war in France, he witnessed and survived the Black Death as well as the Peasants’ Revolt, he traveled across Spain and Italy, he oversaw the construction of famous architectural works, and he lived long enough to serve three different English kings. This is Chaucer’s best tale, the story of his own life.

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The First Part – Chaucer’s Early Life

Likely born in 1342 or 1343, Chaucer grew up in well-above-average means, living with servants, privately tutored in a nice house on Thames Street. To prepare him for his service at court, his parents, John Chaucer and Agnes Copton, also gave him an expensive education. John was a wealthy vintner and the family could certainly afford it.

The name Chaucer actually stems from the French word “chaucier”, which means a maker of hose or shoes. And this comes from our poet’s grandfather Robert Chaucer, who lived on Cordwainer Street, hence why he was called Robert Chaucer in London, even if he was a vintner who simply preferred to live in the prominent leather district. John, the poet’s father, aside from being well-to-do, was also in service to Edward III. In 1338, we can picture Chaucer’s father ensuring the quality of wine for the king’s court. Agnes Copton, Chaucer’s mother, had a well-to-do family as well with good property in London that was passed down to her. But she also rose high thanks to the connections of her first husband, who was related to the great William de Norwell, who served the king as keeper of the wardrobe.

13 years before his son Geoffrey was born, John Chaucer, who was then only 15-years-old, joined Edward III in 1327 against the Scots in a disastrous campaign. After crossing the Tyne in an attempt to catch the Scots in a return trip, conditions got so bad at camp that the English murdered each other over bread. Days later another of the camps would be attacked during sleep. Lord Douglas and his Scots slew many young Englishmen in a brief moment before riding away, so we should be glad John wasn’t one of those poor souls, otherwise our beloved poet never would’ve been born.

In 1340, a few years before John and Agnes’s son was born, Edward III assumed the throne of France, and the navy drubbed the French at Sluys, meaning Geoffrey was born in a beautiful time to rise as an Englishman. Chaucer was raised in London, like we can expect most middling class boys were raised, with a combination of tough love (beatings) and tremendous affection from his wet nurse and parents. And the district where he lived, close to a city gate, allowed him to see all the different roles and types of people medieval England had to offer. He also lived with animals, chickens, pigs, and servants sharing the house.

Around the age of seven, Chaucer moved with his family to Southampton, where John had been made deputy to the king’s butler, collecting import duties on wine shipments. John must’ve been good at his job because he was also made the king’s customs collector for wool exports in the same year. This is the time when Geoffrey would have begun proper schooling as well, which was likely attached to a church or cathedral, where he would be taught manners to separate him from other young boys who weren’t as fortunate. Here Geoffrey would learn his alphabet from a horn-book, and later from a primer that contained more psalms to practice reading, which was always done out loud by the way. Chaucer, because English wasn’t a school language until the late 1400s, would also be learning his lessons in French. After two years in Southampton, Chaucer and his family moved back to London, where a year earlier the plague had reached the city, killing somewhere between one-fourth to one-third of its population, including his older stepbrother Thomas Heyron as well as other family. Although unfortunate, this death would mean Geoffrey’s family inherited even more good property in London. Again, fate worked its will on our poet, for we should be glad Chaucer was in Southampton in 1348 or he may never have lived to write his first poem.

Chaucer had grown up to the age of eight in an England where the brightest minds were working in the churches, where overpopulation of towns left paupers huddled in small houses, but by the age of nine, when the plague struck, his world was on its head, and the kindest, brightest minds had perished helping others, and the fall of population had made a sudden shortage of labor. This would certainly have an effect on any young mind. The plague changed Europe’s philosophy and understanding of the divine, giving rise to a new branch of thought, and this was very timely for people who were falling back to old writings like Boethius’s The Consolation of Philosophy for clarity, one of the works that would greatly influence how Chaucer viewed the world and which he would later translate into Middle English.

After 1350, Chaucer returned to school, possibly the almonry cathedral school at Saint Paul’s, where there was known to be a great collection of books donated by the late William Ravenstone and William Tolleshunt, which probably explains how Chaucer got early knowledge of the Latin classics–a testament to the power of Christian charity! While Chaucer learned grammar (the trivium) in this London school, we can imagine him reading and loving Dionysius Cato for the first time, and falling in love with language, grammar, logic, and rhetoric. Here in this stage is also where Chaucer would meet ancient and fellow medieval writers that would stick with him in his mind for the rest of his life, influencing what he thought and wrote, including Priscian, Homer, Ovid, Virgil, Statius, Lucan, Aristotle, Boethius, and Macrobius–writers that would speak to his imagination of how the universe works and his love for intellectual thought and probing into realms which most modern men, due to lack of good books, never delve into.

Around the age of sixteen, when males were treated as fully grown men compared to today’s standards, Chaucer was already working his way up in the world as a servant in Elizabeth, Countess of Ulster’s household. Elizabeth was the wife of Prince Lionel, Edward III’s third son, so Chaucer was thrusted into royal circles at a young age. This was 1357 and although Chaucer was done with school, he was expected to continue studies in French and Latin, especially as his task as a servant likely involved a lot of copying, recording, reading, accounting, etc. No evidence survives of him also writing poems at this time, although it is likely he did, as it wouldn’t be long before he became a favored court poet with royal-house patronage.

Like most noble families, the Countess of Ulster was never in one place for long and would travel from London to Southampton, to Woodstock, to Hatfield with her whole retinue in a span of a single year. Between 1357 and 1359, this constant traveling most definitely aided Chaucer’s young mind, to travel with her and see the world as an adult sees it, to witness the contrast between poor and rich and the human habits and attitudes that can either make life demoralizing or rewarding. Chaucer also got to meet all the royal family during his youthful servant days in Elizabeth’s court, including his future close friend John of Gaunt, Edward III’s fourth son, which helps to explain why his first poetry book, The Book of the Duchess, is a tribute to Gaunt praising his first wife Blanche of Lancaster.

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The Second Part – Chaucer’s Early-Middle Life

Poems and works associated with this period (mid 1360s to early 1380s):

• The Book of the Duchess (ca. 1368 to 1372)
• Early development of ideas that would later appear in Troilus and Criseyde
• The House of Fame (ca. 1379 to 1380)
• The Parliament of Fowls (ca. 1380 to 1382)

In 1359, Chaucer began his service in the war against France, at first briefly as a fighter and mostly as a diplomat. We know this service in war lasted long, because in 1386 he testified in court on a question of heraldic precedence, and said “I have borne arms for twenty-seven years.” The travel to France in 1359 was not like a modern vacation at all, but marching through a destroyed and abandoned countryside, until Chaucer and the wing he was with got captured by the French between December and January 1360. The king himself would put sixteen pounds towards his ransom. After being ransomed, he likely returned to Prince Lionel’s service in the war, and wouldn’t return home in England until May 18th 1360, having been paid twenty-four pounds to carry Lionel’s letters.

Medieval warfare is certainly full of glory, but the side of war Chaucer saw on his brief campaign wasn’t very glorious at all. Despite continuing to be a proud Englishman, we can imagine that it was this encounter with the dim side of war that helped to egg him on further toward a life of books.

From 1360 to 1367, when Chaucer was aging from twenty-one to twenty-seven, he was learning more about life from listening to great men like Froissart and Deschamps in London and Oxford, more than he could ever learn digging latrines in France. These would be the years, too, when Chaucer translated Romance of the Rose into Middle English, which would propel his skill by raw practice. Chaucer also, while doing all this, attended law school. In 1368 to 1372, Chaucer’s first original book of poetry would prove his mastery. And henceforth he would work as a master, having reached a skill that no one currently living in his world of courtly love and classical learning could compare. The practical employment Chaucer would have in later life, serving various roles for the king and court as a wartime diplomat, proved how his law training was necessary for the amazing life he lived, not only because he needed it for his employment, but needed it for his poetry as well, because his writings are full of vocabulary that would be really hard to know if you weren’t a law student. At this time, when Chaucer was studying law at the Inner Temple, which would require him to leave the city every day, is when he likely could’ve stumbled on the friar he supposedly beat up and had to pay a fine for. It was only a fine for two shillings, if the story is true, which it probably isn’t, but if it is true it suggests some sympathy was given his way, meaning the friar must’ve deserved it. In any case, something real certainly did inspire his literary attack against friars who lived secret double lives and had no place teaching right from wrong.

In September 1366, Chaucer would marry Philippa Roet (also known as Philippa Pan), daughter of Sir Paon of Roet, and they would eventually have four children together, two sons and two daughters. But their romance began earlier, possibly as early as 1357. The culture Chaucer lived in meant courtly romance was inevitable, where affairs were sinful yet normalized. We know Chaucer wrote love songs because his friend, John Gower, wrote that Chaucer in his youth spread songs through the countryside as a poet of Venus. So it’s likely some love songs he made were for Philippa. Even so, as a poet who wrote love songs, he thought himself as a servant of Love’s servant in Troilus and Criseyde. He was more pious than many other men would have been with his talent. Although it is also contested that he was less pious than he claimed when it came to premarital romance. In either case, his early career as a poet revolved around courtly love, that is fair to say. But remember this courtly culture of normalized love affairs for an upcoming discussion, because it’s important when it comes to a theory about Chaucer’s own role as a parent which I’ll get to shortly.

It was in September 1369 that Chaucer joined Gaunt on a raid in France. He received 10 pounds for his service in this campaign and it is suspected he was there to entertain Blanche, Gaunt’s wife. Unfortunately, Blanche died of the plague and Chaucer watched how the death changed Gaunt, how it made him march harder toward war. On campaign this is when Chaucer began his poem The Book of the Duchess, an elegy deserving of his friendship to Gaunt. This campaign, and the harshness of the war overall that proved chivalry was dead, certainly had an impact on Chaucer’s respect for the famed chivalry that had once been, before evil tactics and black powder changed the face of war forever. To encapsulate what had been lost, undoubtedly, Chaucer later wrote The Knight’s Tale to reveal chivalry’s decay line by line.

Around this time in the late ’60s and early ’70s, Chaucer was likely steeped in Oxford learning. His religious views that come out in his poetry are certainly in line with what was popular at Oxford to say the least. By this time, thanks to a century or more of Oxford professors praising diversity in language, including Greek, Hebrew, and Arabic from abroad, Oxford was primed to introduce Chaucer to an array of literary and scientific books. By the end of this period of study, Chaucer had fully adorned himself in a rich education that would make modern PhDs look easy in comparison. Chaucer’s association with Oxford circles, whether he was actually a student there or merely mingled with the ideas in court, certainly introduced him to Lollardy or the heretical ideas of John Wycliffe, a sort of proto-Protestantism, and this is when he was met with the the town-versus-gown atmosphere that young liberal students created under their secular teachers. Chaucer never went full-bore into Oxford heresy, but his liberty in critiquing rich sinful clergy is certainly an element taken from Oxford thinking.

In February to May of 1366, we can really see how working for the Countess of Ulster had been Chaucer’s gateway into a role of royal service, as during this time he was traveling in Spain on a secret diplomatic mission for Edward III, whom you’ll remember had personally paid toward Chaucer’s ransom in France. Later in 1366, or in early 1367, his father John died. 1366 was also the year Chaucer married Philippa Roet. So this was quite the twelve-month for our poet!–and do you remember what I said about the courtly culture of normalized love affairs I mentioned earlier? It has been speculated by some like Russell Krauss (though it remains unproven, and many modern scholars consider the theory unlikely) that Philippa’s daughter Elizabeth (born around the time of their marriage) may have actually been the child of Gaunt, not Geoffrey. This would explain why Philippa married someone below her station, and why Gaunt granted Chaucer twenty marks after the birth, and why the marriage may have been less romantic than what we’d expect a romantic poet’s love life to be. Either way, Chaucer was continually blessed by Gaunt, really suggesting at least they were very close friends.

Speaking of close friendships with Gaunt, in 1374 Chaucer was given a free lease for life on a house above Aldgate, and was employed as controller of customs and subsidy for wools, hides, and woolfells for part of London, as well as controller of petty customs of wines for part of London. He was then given a further ten pounds by Gaunt on top of the annual exchequer annuity of twenty marks he was already granted back in 1367. This meant Chaucer was now financially set. And as many artists know, this helps a long way in having the time and peace of mind needed to pour hours of love into art. It has also been suggested by some that Thomas Chaucer may have actually been Gaunt’s son as well, which would help explain why Gaunt appears to have been even more generous to Thomas in later life than to Geoffrey during this time, which is hard to imagine right! Geoffrey, being a royalist and knowing full well the nature of courtly love affairs, may have taken on this task of raising Gaunt’s secret children willingly, if the rumors are true that is, knowing full well Gaunt, his wife, and himself were all players and beneficiaries of the courtly love culture they lived in.

Earlier, in 1372 to ’73 Chaucer traveled to Italy to continue the aforementioned wartime diplomacy. During this period he encountered the works of major Italian writers, including Dante, Boccaccio, and Petrarch, which would go on to impact his poetry quite heavily. This trip to Italy also opened Chaucer’s eyes to Italian architecture and the ruins of the ancient world, giving him a grander respect for history and pre-Christian religion. And this insight into architecture was probably why he became a clerk of the king’s works later in his career.

More than Boccaccio or Petrarch, the great Italian influence that affected Chaucer on his travels the most was his deep engagement with Dante’s work. It was in 1374, following Gaunt’s return to England due to a failed military campaign, that Chaucer began receiving all those abovementioned blessings that would aid him to becoming a grand poet. We’ve talked about his gifts of cash and his house on Aldgate, but as he became an intellectual ornament of the court Chaucer was also rewarded for his poetry readings themselves, which no doubt motivated him to write more.

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The Third Part – Chaucer’s High-Middle Life

Poems and works associated with this period (early to late 1380s):

• Troilus and Criseyde (ca. 1382 to 1386)
• The Legend of Good Women (ca. 1386 to 1388)
• Beginning of The Canterbury Tales (ca. 1387 onward)

During the last years of Edward III’s reign (he died in 1377), Chaucer had much opportunity as controller of customs to become corrupt like his associates were known to be. However, there is no good evidence to suggest he took those opportunities. Associates like Brembre, who made corruption in the king’s service seem normal, were likely ignored rather than emulated. Perhaps this loyalty speaks to Chaucer’s royal favor with Richard II and later Henry IV. So, not too surprisingly, in 1377 Chaucer was sent on another diplomatic mission to secure a marriage alliance between France and England to end the war. But Marie of France died, young Prince Richard still had no wife, and the mission failed. Interestingly, it was during this voyage that Chaucer met Guichard d’Angle, who probably filled Chaucer’s ear with grand stories of how he was captured by Pedro the Cruel’s bastard rival Trastámara in 1372. Chaucer was already a royalist who favored Pedro the Cruel merely because Gaunt married his daughter Constance in 1371, but we can see why he would later write “O noble, O worthy Petro” in The Canterbury Tales if d’Angle shared stories of how Trastámara had treated him roughly in prison.

After the failed marriage attempt, Edward III died, and right away Chaucer was sent again to arrange a marriage between who was now King Richard II and Caterina of Milan, to create an Italian alliance that would threaten France from the south. But again the marriage failed. These two failures were not Chaucer’s fault, as he was an impressive speaker and poet (the perfect man for the job, even if it was his Canterbury Tales in the ’90s that would eventually make him famous in Italy), but he certainly got to learn the ways of diplomatic marriage, and more life experience to aid his later poetic works.

In 1381, we see the Peasants’ Revolt. Being a royalist and being constantly away on travel, Chaucer wasn’t an advocate for the less fortunate like many celebrities pretend to be today. His poetry doesn’t hide his stereotypical royal view of peasants–that they’re dumb and dangerous and funny–and we can even assume he had a favorable view of Alice Perrers, Edward III’s evil mistress, for he was friends with her friends and she likely was a patron of his work. Similarly to how Alice Perrers was targeted by Parliament for abusing Edward III’s love financially, his friend Gaunt was targeted by the Peasants’ Revolt after his efforts to change taxes between 1377 to 1379. And with the poll taxes of 1377, 1379, and especially the flat-rate poll tax of 1380, Chaucer must’ve personally heard the hatred against Gaunt from his work in the customs house, yet still he did his duty collecting customs all the same. In May 1381, the revolt spread like wildfire. When the peasants marched on London led by Wat Tyler, it’s likely Chaucer saw them coming from his house on Aldgate, but he never reveals his true feelings. The peasants were there to kill Flemings, as they believed the foreigners were sucking wealth out of England, and Chaucer’s wife Philippa was Flemish, so we can at least guess what he might have felt seeing the horde arrive (fear for his life). In any case, he survived the butchery, thank goodness!

By 1382, Chaucer had more time than previously for writing poetry, mostly because Richard II was already married to Anne of Bohemia and so his work as a diplomat was over. Now Chaucer’s only work was being at the customs house, which while demanding wasn’t overly demanding, and so it left him with time to write, which we know because in the ’80s is when he would begin his most famous works–The Canterbury Tales.

In July 1386, Gaunt left England to pursue his crown of Castile, leaving his good friend Chaucer to get caught in the political crossfire between Richard II, who was now nineteen, and Gaunt’s younger brother Thomas of Woodstock, now Duke of Gloucester. Several months after Gaunt had left England, Chaucer surrendered his job as customs controller likely because Gloucester would be scrutinizing anyone who had profited from customs collection positions. Being a royalist, we can understand if Chaucer felt threatened by Gloucester’s rise even if he had never turned corrupt like Brembre. In any case, Chaucer wisely moved to Greenwich after long preparation, giving up his house on Aldgate, and during this time that Chaucer lived in Greenwich, a place which at that time was a beautiful countryside, he was likely given new inspiration for poetry material. Being an observant writer meant Chaucer certainly made use of living in the country to give him new perspectives on life, as it does to everyone, which we can see in The Miller’s Tale and The Reeve’s Tale.

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The Fourth Part – Chaucer’s Late Life

Poems and works associated with this later period (late 1380s to 1390s):

• Continued composition and revision of The Canterbury Tales until his death
• Treatise on the Astrolabe (ca. 1391)
• Various shorter poems and revisions of earlier works
• The Retraction (added in his final years)

Back in 1385, while still serving as customs controller, Chaucer was made a justice of the peace for Kent. His job as justice of the peace wouldn’t typically be a super demanding position, but 1386 was the year when the bickerings between Gloucester and Richard II would really take off with the Wonderful Parliament. Because Gaunt was away in Castile, and because the French were planning another invasion, which Gloucester used as an excuse to strengthen Parliament, Chaucer was left on his own to be pushed out of his controller position while using his life’s wisdom to avoid Gloucester’s line of fire, which we already mentioned is likely why he prudently moved into the country. Chaucer was on the king’s side, and now the courtly role that had propelled him in life was the very reason he would slip behind the curtain, probably wishing he could just work on his poetry instead of dealing with all this political drama.

Chaucer prudently stayed in the shadows when Gloucester’s supporters were executing Richard II’s counselors, such as Brembre, that scoundrel. But on May third, 1389, Richard II was by now aged twenty-two, meaning he was of full age to rule the kingdom in person, and in November, Chaucer’s friend Gaunt returned to England. Before Gaunt’s return in 1389, however, Chaucer had been having hard times, not only in avoiding politics but in being a widower, as his wife Phillipa had died in the summer of 1387. One can speculate his wife’s death is why Chaucer never showed himself in court. In either case, we should be glad he never got in Gloucester’s way (too many close calls, right!).

In 1388, Chaucer’s exchequer annuity was sold for a lump sum due to financial weakness from losing his best paying job. Unsurprisingly, then, 1388 was also the year Chaucer was sued for debt. By May 1389, however, Richard II began restoring his friends that Gloucester had removed back into office, which included appointing Chaucer as a clerk of the king’s works in July, a job he would hold until June 1391 and that would greatly restore his finances. And so, due to this position, people who simply love Chaucer’s poetry might also be amazed to learn Chaucer was responsible for overseeing construction at Westminster Palace, the Tower of London, Berkhampstead Castle, and other important places, meaning he had a lasting touch on the physical appearance of England let alone the literary atmosphere.

On September third, 1390, because being a clerk of the king’s works required lots of traveling between projects to ensure the payment of building materials, Chaucer was robbed in Kent by a gang of former soldiers, stealing twenty pounds belonging to Richard II. And after many of these gangsters had been hanged for different crimes, Chaucer was quickly relieved from having to repay the twenty pounds. For me, because of everything else he had to deal with in life, this speaks to his will to focus on writing despite external drama that might make modern writers too distracted to focus, which I believe is a great skill every artist needs. After 1391, however, Chaucer had far less distractions than he did for most of his life, and partly because Richard II was doing well in his struggle against Gloucester (who interestingly would later be murdered, likely on Richard II’s orders, in 1397), Chaucer was also doing well, now receiving payments on time and acting as sub-forester of Petherton Forest with no further risk of being pushed out of favor.

As a widower, and with his sons either in school or serving Gaunt’s court, Chaucer was now finally at ease reaping the hard work of his life, which must’ve come with much more time to write (yay!). In late 1399, he moved to a smaller house connected to Westminster Abbey which was protected by sanctuary so that creditors couldn’t harass him for small debts he owed from his old jobs as controller of customs and clerk of various works. Although while he avoided small debts, we can see he did visit London to settle debts in court several times. Because Chaucer was now living at ease as his own man, now famous across Europe thanks to his Canterbury Tales, he could now tailor his poetry to meet his own satisfaction rather than that of the court, and so we see him altering his older works during this time.

Earlier in 1399, Gaunt died, taking away Richard II’s most powerful supporter. And having recently tried all his enemies for treason, and now marching around England harassing his pettier enemies, Richard II had understandably become hated by much of England. He resorted to scrutinizing his own court, always in fear of further treason, and so even Chaucer must’ve been on his toes when reciting poems in court, especially after Gaunt’s holdings went to his son, Henry Bolingbroke, who was Richard II’s enemy. Believing he was protected by heaven due to his belief in absolutism, Richard II boldly met Bolingbroke under deceitful pretenses and was taken prisoner, eventually dying of starvation at Pontefract on February 14, 1400. Being a royalist, Chaucer accepted the new king, Henry IV, who made it his own pleasure to restore and increase Chaucer’s annuity to forty marks a year instead of twenty, perhaps because he wished to respect his father Gaunt’s friendship with the poet, and he even continued Richard II’s pledge of a yearly tun of wine. Chaucer’s son, Thomas, would also go on to rise in high positions under Henry IV and Henry V.

Some historians believe that the Retraction Chaucer added to his tale along with illustrations of him holding beads in later manuscripts point to him becoming religious on his deathbed. He’d always been religious though, but unlike a monk he also praised earthly romantic love between humans, not just love between humans and God, and must’ve believed any form of love was better than no love at all. In any case, in his final years Chaucer added the Retraction, in which he asked for forgiveness for the sinful nature of his poetry. Even so, he probably understood more than any young thinker living well today that he was only human. And so, at roughly the age of 57, on October 25, 1400, The Canterbury Tales were left unfinished, yet they were left spectacular all the same.

If you are an artist or have grand goals like myself, you can see why Chaucer’s best tale, the tale of his own life, is so inspiring. The major lesson I learned from reading about his life is that while one must take on some responsibilities in order to have the financial luxury to follow one’s true passion with peace of mind, too much responsibility at the same time can take away the luxury of time for pursuing one’s true passion. Life is short, so when it’s right to do so we must put all drama aside and focus on what really matters to us, whatever that may be in your heart. For Chaucer, it wasn’t collecting customs or appearing in court–it was writing poetry. And whatever his fortune at birth and his blessings in life, I’m so grateful he still found the discipline to render his true service to humanity.

The Ende

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My sources, you ask?

Source: Artificial intelligence did NOT write this article! This article is comprised of all my notes taken from reading The Life and Times of Chaucer by John Gardner over the course of early 2026, which I edited myself into a cohesive narrative in my own style. However, I did heavily fact check the article with SuperGrok expert mode throughout June 30th and July 1st, 2026, and accepted many of its corrections because newer academia has shed more light on Chaucer’s life since John Gardner wrote his often speculative narrative.

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