On 25 July 1386, three young men disembarked from a Portuguese galley at the port of Corunna. Landing on the northwest Spanish coast were Ralph Bulmere, just old enough to receive his inheritance at home; Baldwin Saint George from Cambridgeshire; and Thomas Chaucer, son of writer and diplomat Geoffrey Chaucer. They had come to win their spurs in one of the most ambitious military campaigns of the late 14th century: the invasion of Castile by John of Gaunt.


At that time, Castile was the largest of four Christian kingdoms in the Iberian peninsula. Sandwiched between Portugal to the west and Aragon and Navarre to the east, and with the Muslim emirate of Granada to the south, Castile also encompassed León and coastal Galicia, site of Corunna. And in the 14th century it was embroiled in an interminable tussle for succession between England and France: the Hundred Years’ War.

Castile’s involvement had peaked two decades earlier with the pitched battle of Najéra in Navarre on 3 April 1367, in which the army of the Black Prince, heir to English king Edward III, charged across a dusty plain at Castilian and French forces – and emerged victorious. Leading the vanguard was John of Gaunt, the Black Prince’s younger brother. Najéra was his formative experience of battle, and sparked a 20-year-long obsession with Spanish conquest.

Cruel twist of fate

John was not only a prince but also the most powerful magnate in England, with wealth and influence to rival the crown. His possessions included England’s richest duchy, Lancaster, and he also inherited lands in northern France as well as northern and southern England. An astute politician, John was deeply loyal to his family and his father Edward III’s martial interests, and spent his early career as a diplomat. He saw Castile as the gateway to both personal power and Plantagenet expansion into Europe.

An opportunity soon fell into his lap. In 1369, Enrique Trastámara, a French ally and claimant to the crown of Castile, murdered his half brother King Pedro I “The Cruel”, an ally of England. Pedro’s daughters, Constance and Isabella, fled to the Black Prince for protection and in 1371 John of Gaunt, recently widowed, married Constance near Bordeaux. The following year he was formally entitled “King of Castile and León” by right of his wife, and aspired to drive an army into Spain, oust Enrique and rule Castile.

Initially, John’s ambitions were thwarted by the demands of domestic politics. The Black Prince’s health deteriorated following a long sickness contracted during that fateful Spanish campaign, and Edward III suffered a series of strokes. When both died, in 1376 and 1377 respectively, John became the effective regent of England in the minority reign of his nephew (the Black Prince’s son King Richard II). Despite these distractions, though, he continued to style himself king of Castile, displaced in England.

Then, after years of impasse, in 1385 the army of Portuguese King João I defeated Castile and allies at the battle of Aljubarrota, leaving the Spanish kingdom weakened. With the blessing of Richard II and parliament, John sailed from Plymouth to conquer Castile and rule it as a Plantagenet domain. Before John’s departure, Richard gave his uncle the gift of “a golden crown... and ordered all to call the duke King of Spain, and to accord him royal honours on all occasions”.

The English arrival at Corunna was meticulously timed. John’s party landed on the feast day of James the Apostle (Santiago), patron saint of Spain – emblematic of his desire for his kingship to be seen as God-given. Also disembarking were goldsmiths, painters, embroiderers, cooks, minstrels and chaplains, as well as John’s wife and three daughters, Philippa, Elizabeth and Catherine, and their ladies. The contingent, which included young Ralph, Baldwin and Thomas, also counted among its number John’s trusted Castilian chancellor, Juan Gutiérrez, and Richard Burley, marshal of his army, who had fought alongside him at Najéra.

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Another campaigner was Sir Thomas Percy, keeper of Roxburgh Castle, who invested heavily in John’s claim and brought with him more than 200 men. John had earlier requested that Percy pay his own expenses, and those of his men, in return for profits from the war – such as loot or prisoners to be ransomed – which might amount to a significant sum.

John’s first target was the holy city of Santiago de Compostela, sacred heart of Spain. As he had hoped, there was no conflict: terms were quickly agreed, and he was ceremonially handed the keys to the city before crowds of spectators. At the town of Orense, in a manner befitting a king, John established a chancery and had his own coins minted using bullion transported from Plymouth. He clearly intended a perpetual English occupation of Castile – but this would not go unchallenged.

The news soon reached Juan Trastámara, Enrique’s son and successor, at his castle in Zamora, south-east of Galicia. Juan, who had anticipated an attack via Portugal, launched a diatribe against the English, branding them unholy “schismatics”. Left with only a skeletal fighting force after defeat at Aljubarrota, Juan sought French aid. Oliver de Clisson, the constable of France, agreed to help; he was stationed in Castile with a small contingent of soldiers, and French king Charles VI promised another 2,000 men at arms.

Raising a red flag

Juan was advised to adopt the French tactics of evasion and scorched earth. Crops were burned and, as black smoke billowed across the plains, towns and villages were stripped of supplies. An abundance of strongholds littered the plains of Castile, reflected in the kingdom’s arms – golden castles upon a red flag – and many residents of towns and villages were evacuated to fortified garrisons. Bridges were destroyed, livestock was removed from pasture, and personal letters were intercepted to detect evidence of any traitors conspiring with the English.

In a bid to stymie his advance, John’s enemies burned crops and stripped towns of supplies

Juan had made Castile as hostile to the enemy as possible in the hope that John’s army would perish in the late summer heat, when the ground was so arid and barren the men could “hardly breathe… their mouths were full of sand”. And indeed the chronicler Jean Froissart wrote that “the days grew hotter and hotter, until no one dared to go out riding after nine o’clock unless he wanted to be scorched by the sun”. The hopeful mood of John’s army as it disembarked at Corunna now evaporated in the blazing sun that blasted the barren Castilian landscape. The situation worsened in August when a sickness swept through the English ranks, claiming many lives; in September it took Lord Walter Fitzwalter, one of John’s most valued men.

Shady dealings

Trapped in Galicia with a rapidly sickening army, John was left with two options: sue for peace or make a formal alliance with the Portuguese. So in November 1386 he met João I in the village of Ponte de Mouro, on the Castilian-Portuguese border, to discuss the terms of a military pact. In the shade of a canopy, the two men formalised plans for a major Anglo-Portuguese invasion of Castile. João promised to lead 5,000 men himself and, in return, John would extend Portuguese territory by granting land along the border. The pact would be sealed with a marriage between João and Philippa of Lancaster, John’s eldest daughter, who would become queen of Portugal.

The campaign was revived. It soon became apparent, though, that John’s influence did not extend beyond his own men. Soon after the Portuguese army moved out of Porto at the end of February 1387, there was an awkward exchange in which John learned that the Portuguese had demoted him. Rather than leading the vanguard, as he had at the battle of Najéra, that role was claimed by Nun’Alvarez, constable of Portugal. João, uncomfortably torn between his commander and his new father-in law, did little to improve the situation for John. This slight showed that control lay with João and his Portuguese army, not with the English. The alliance that had seemed so promising had in fact compromised John’s influence.

John of Gaunt (far left, in blue, under the arms of England and France) feasts with João I of Portugal
John of Gaunt (far left, in blue, under the arms of England and France) feasts with João I of Portugal. Despite this depiction of amity, the Portuguese were deeply suspicious about English intentions on the Iberian peninsula (Photo by Photo 12/ Universal Images Group via Getty Images)

The agreed objective was the city of León, a tortuous journey that took the army through Portugal and Castile. The route passed a series of garrisons, opportune targets for siege, conquest and plunder. Among the first was Benavente, south of León. Without siege engines, an attack on the largest garrison in Castile was ambitious, and the attackers first made camp away from the town, out of range of the bowmen on the high walls. However, Benavente was also occupied by French soldiers, and English and French began to fraternise here for the first – but not the last – time during the invasion.

Many who served John in Spain were seasoned soldiers, having experienced campaigns in France. Some of the French in Benavente recognised English men, calling out to them and, in a display of traditional chivalry, arranging jousts and tilts. The Portuguese looked on in disbelief, and a wave of scepticism – about the loyalty of the English soldiers, and even about John’s intentions in Castile – swept through their ranks. They saw the Englishmen’s actions as an insult to their own loyalty. The animosity already fermenting among their leaders thus infiltrated the rest of the men.

Abandoning hope of taking Benavente, the joint army advanced deeper into Castile to the small town of Valderas where, despite the inhabitants’ attempts to thwart pillaging, the ample pickings attracted the attention of hungry soldiers, deepening the rift. As the army entered the town, Portuguese and English began to fight over the potential booty, until it was decreed that the English could plunder for the first half of the day, then the Portuguese for the second. After a few hours, though, agitated Portuguese soldiers stormed the town, leading to further skirmishes until João galloped forward and ordered his soldiers to stand down.

By this point, the relationship had completely disintegrated; there was more friction between the English and the Portuguese than there was action against the Castilian enemy. In an attempt to rescue the campaign, they took aim at Villalpando, a garrison south of León controlled by the constable of France, Olivier de Clisson, with the intention of an assault leading to a pitched battle. That hope was again thwarted by the climate.

There was more friction between the English and Portuguese than war with the enemy

As spring turned to summer, the sun scorched the earth at midday and the horses, weak and parched, mauled the hard, dry ground for want of grass. Thirsty soldiers sucked at grapes and drank heavy Portuguese wine, becoming drunk and dehydrated, many stripping off their clothes in an attempt to cool off. Temperatures plummeted overnight. Then, writes Froissart, “came the morning chill which struck through their whole bodies, giving them sickness and fever and afflicting them with flux [dysentery]”. These fluctuations in temperature, combined with malnourishment and dehydration – from the wine and agonising bouts of dysentery – led to more deaths in the camp and the further spread of disease.

This wave of deaths stole many of John’s best men and, with them, his morale. By the end of May he had lost Lord Scales, Lord Poynings, his son-in-law Thomas Morieux, his chamberlain John Marmion and, most painfully, his dearest friend and loyal marshal of his army, Simon Burley.

John’s response was to retreat into his own company. “The Duke of Lancaster was at his wits’ end and often weighed down by anxiety,” wrote Froissart. “He saw his men – the best of them – exhausted and ill and taking to their beds, while he himself felt weary that he lay in his bed without moving... yet from time to time he would get up and do his best to seem cheerful, so not to discourage his men.”

Disease had shadowed the English campaign through Spain, and the loss of men was immense: more than 800 squires, archers, knights and barons perished at Villalpando alone, and survivors lamented that “our lord of Lancaster has brought us to Spain to die”. One knight, Thomas Quinebery, escaped Spain and met Jean Froissart on his way home to England, enfeebled but grateful for his life. He informed the chronicler that John had lost at least half of his army.

And what of Ralph Bulmere, Thomas Chaucer and Baldwin Saint George, the eager young squires who had disembarked at Corunna in July 1386? We know that the latter two made it back to England. But if Quinebery’s estimation is correct, statistically it’s unlikely that their companion survived the summer.

English soldiers now began to desert the disease-infested camp at Villalpando, where John waited to receive word on terms for a truce from Juan Trastámara. He was forced to come to terms not only with his failure to take Castile but also with the huge loss of life. As soldiers packed up and left the camp, João angrily called them traitors, and John bowed his head and wept into his horse’s mane.

As the English and French jousted, the Portuguese were forced to scavenge birds’ nests on the side of the road

Having failed to take Villalpando, let alone León, the remaining army retreated towards Portugal, camping outside the walls of Salamanca en route. Seeing the sorry state of the ravenous English men, French soldiers who occupied the city took pity on them, delivering cartloads of supplies to the camp. This offering was reciprocated with an invitation to the French, and a knight called Renaud de Roye brought 50 knights and squires to a joust arranged by the English. The Portuguese, meanwhile, were forced to scavenge birds’ nests on the sides of the roads for sustenance.

A crown of gold

Back in Portugal in early June, John of Gaunt met the ambassadors of Juan Trastámara at the castle of Trancoso, and appointed Sir Thomas Percy to conduct peace negotiations. A key term was the marriage of Juan’s son, the soon-to-be prince of Asturias, to Catherine of Lancaster, John’s daughter. The marriage would guarantee succession to the throne of Castile, grafting John’s bloodline onto the dynastic family tree of Spain. “Immense riches” were sent to John, including mules laden with crates of gold – payment for relinquishing his claim to Castile.

So a sorrowful John of Gaunt abandoned the goal he had pursued for 20 years. As a parting gesture, he arranged for the delivery of a personal gift to Juan Trastámara: the gleaming golden crown given by Richard II to John as he left England the previous year, full of ambition and hope.

Following the failure of his Castile campaign, John’s interest in Spain waned. Returning to England in 1389, he promoted clemency and spent his final years as a peacemaker, playing a political long game amid Richard’s volatile tyranny in an attempt to protect his family and legacy.

When John of Gaunt died at Leicester Castle in February 1399, his son, Henry Bolingbroke, was in exile and all seemed lost. Yet John’s legacy did endure. Young Bolingbroke returned to claim the English throne as Henry IV. And John’s daughter Catherine became queen consort and then regent of Castile. Through her arose the most famous alliance of the 16th century – the marriage between her great-granddaughter, Catherine of Aragon, and Henry VIII. The dynasty had come full circle.

Despite his failure in Castile, John of Gaunt became the father of long lines of famous monarchs in England and Spain – kings and queens who dominate the pages of history books to this day.


This article was first published in the May 2021 edition of BBC History Magazine


Helen CarrHistorian and author

Helen Carr is an historian, writer, TV and podcast producer, specialising in medieval history and public history.