The man who would be King of Castile

“This royal throne of kings, this scepter’d isle,

This earth of majesty, this seat of Mars,

This other Eden, demi-paradise,

This fortress built by Nature for herself

Against infection and the hand of war,

This happy breed of men, this little world,

This precious stone set in the silver sea,

Which serves it in the office of a wall,

Or as a moat defensive to a house,

Against the envy of less happier lands,

This blessed plot, this earth, this realm, this England,”

William Shakespeare. Richard II, Act 2, Scene 1.

It is somewhat ironic that Shakespeare’s most famous evocation of English pride and patriotism is given to John of Gaunt, someone who in real life was born in Ghent (in today’s Belgium), served as Duke of Aquitaine (southwest France), and spent much of his adult life in pursuit of the throne of Castile (central Spain).

John of Gaunt’s position at the epicentre of the English monarchy is undisputed: His father (Edward III) was King of England, as was his son from his first marriage (Henry IV), and grandson (Henry V). And then, 86 years after John’s death, his great-grandson, from his initially illegitimate third marriage to Katherine Swynford, ascended the throne as Henry VII, founder of Tudor dynasty.

But John himself was never King of England and this perhaps explains why he was so obsessed with gaining a regal title for himself to add to the plethora of aristocratic titles and domains he had inherited or acquired since early childhood.

The self-proclaimed King of Castile and Leon

The genesis of John of Gaunt’s Castilian quest probably began when, aged 27, he accompanied his elder brother, the Black Prince, in a military intervention in the Castilian civil war in support of Pedro the Cruel against his insurgent half-brother Enrique Trastámara. The campaign ended in a resounding victory for the Black Prince at the Battle of Nájera in 1367 but that ultimately was of little consequence as Pedro, unsurprisingly, reneged on his promises to the Black Prince and was killed two years later, in hand-to-hand combat by Enrique.

But John did not give up. Following the death of his first wife Blanche of Lancaster, in 1371, he married Pedro’s daughter Constanza, a cynical and calculated move that allowed him to call himself King of Castile even though Enrique Trastámara actually occupied the throne at the time and remained there until his death in 1379 when he was succeeded by his son Juan.

John of Gaunt was unable to claim his crown in person at this time because he lacked the funds for a military campaign and was busy with the political turmoil created by the death of his father Edward and succession of his ten-year-old nephew Richard in 1377. To make matters worse, the Westminster government was essentially bankrupt during the succession period and decided to impose a new poll tax on everyone in the land at an equal rate from the very richest merchant to the poorest peasant. This combined with other repressive measures such as the Statute of Labourers, which capped wages, and the abuse of power by the church and other local landlords led to Great Rebellion of 1381 when rebels from Kent and Essex stormed the city of London demanding wide-ranging reforms.

John of Gaunt was one of the primary targets of the rebellion. He was probably the richest and most powerful man in the land, next to the king, and also one of the most hated, despised by everyone from London’s mercantile elite to the rural poor.

John’s opulent Savoy Palace on the banks of the Thames, which served as his “Castilian court” in London was ransacked and burnt to the ground by the rebels. John was in the north of England at the time and so avoided the same fate as the equally despised Archbishop of Canterbury who was beheaded by the rebels while hiding in the Tower of London. The main casualties at the Savoy Palace where the 30 rebels who broke into the wine cellar and proceeded to drink its contents before the roof collapsed trapping them inside. The ruined palace was never rebuilt, and today, the Savoy Hotel stands on the site of the carnage.

It is doubtful that John of Gaunt really had much sympathy for “this happy breed of men” that made up the English commons. He was notoriously haughty and vain, and held those “lesser” than him in contempt. That said, he did reportedly treat his “subjects” well, and the good people of his northern powerbase, Leicester, famously closed the city gates in June 1381 to protect their lord’s property when a rumour spread that the rebels were on their way.

When not involved in politics, John spent most of his time in England renovating and decorating his numerous castles and hunting on his northern estates but his mind was always on Castile. Finally, in 1386, when the then 19-year-old Richard II started to exhibit a dangerously independent streak and thought he could do without his uncle’s counsel, the now middle-aged, John of Gaunt had the opportunity to resurrect his Castilian crusade.

He renewed an alliance with Portugal and set off to invade the Kingdom of Castile and Leon via Galicia. The campaign got off to a relatively smooth start but soon bogged down because the Castilian army (backed by the French) refused to engage in a pitched battle with the chivalrous knight. The alliance with Portugal deteriorated quickly and John’s 5,000-strong army was decimated by disease, exhaustion and desertions. Faced with inevitable defeat, John reportedly “bowed his head and wept into his horse’s mane.” He retreated to Salamanca, where he struck a deal with Juan Trastámara, in which he agreed to renounce his claim to the throne of Castile in exchange for the marriage of his daughter from his second marriage, Catherine, to Juan’s son, plus several annual payments of Castilian gold. John retired to lick his wounds in Aquitaine until the agreement with Juan Trastámara was ratified. He only returned to England in November 1389, three years after his departure, on ships “laden with Castilian gold and barrels of Gascon wine.”

A few years later, Catherine became Queen of Castile and went on to act as regent to her son after her husband’s death. A century later, her great granddaughter, Catherine of Aragon would become the first wife of England’s Henry VIII, the great-great-grandson of John of Gaunt.

William Shakespeare wrote Richard II about two hundred years after the events the play describes so it is not surprising that his depiction of John of Gaunt should be coloured by the new economic and political reality of post-Reformation England. By the end of the Sixteenth Century, England was a proto-capitalist nation state that already saw itself as somehow distinct and separate from the European continent.

However, in the second half of the Fourteenth Century, the concept of a nation state as we know it today had not yet been realised and European geography was far more fluid. Everyone in England recognised the king as their ultimate ruler but most ordinary people were still tied by the church and feudal lords to their parish, manor or market town, and it was that locality that probably informed their sense of identity more than the English state. Armies were raised not directly by the state but by individual knights and often included foreign mercenaries willing to work for the highest bidder.

The capital of England, London, was a highly cosmopolitan city, home to merchants from Lombardy, Genoa and Flanders, and its wealth was built on international trade and commerce. John of Gaunt’s own brother-in-law, Geoffrey Chaucer, for example, was the son of a wine trader, spoke French, Italian and Latin, travelled extensively on diplomatic missions across Europe, and for many years acted as controller of customs for the international wool trade. Chaucer is renowned as the founder of the English vernacular literary tradition but his writing was fundamentally informed by earlier French and Italian poets.

Likewise, John of Gaunt cannot be seen as a narrow minded little Englander. He was a thoroughly European knight bound by well-established codes of chivalry. I would suggest a more appropriate evocation of John of Gaunt can be seen in the work of Shakespeare’s Spanish contemporary Miguel de Cervantes. In The Ingenious Gentleman Don Quixote of La Mancha, a self-proclaimed knight errant, approaching 50 years of age, wanders around the plains of Castile with his faithful retinue in search of adventure and chivalrous conquest. Don Quixote’s quest is not the crown but the equally unobtainable and illusory Dulcinea del Toboso. The lanky knight suffers numerous setbacks, injuries and humiliations on his journey before grudgingly returning home without ever seeing his Dulcinea.

John of Gaunt must have known that he was tilting at windmills in his quest for the Castilian throne but such was his sense of self-belief and entitlement that he kept going right until it became clear to all that there was no hope – for him personally at least.

Towards the end of his life, John’s power and influence was slipping away. The increasingly despotic Richard II had exiled John’s eldest son, Henry Bolingbroke, and murdered his youngest brother, Thomas, who he had accused of treason. And following John’s death at the age 59, Richard confiscated all of his land and titles. This was the final insult for Henry Bolingbroke, and it sparked the deadly showdown between the two cousins so dramatically depicted by Shakespeare in the final acts of the play.

Recommend reading:

Juliet Barker, 1381: The Year of the Peasants’ Revolt, Harvard University Press, 2014.

Helen Carr, The Red Prince: John of Gaunt, Oneworld Publications, 2021.

Miguel de Cervantes, The Ingenious Gentleman Don Quixote of La Mancha, 1605, 1615.

William Shakespeare. Richard II, 1595.

Marion Turner, Chaucer: A European Life, Princeton University Press, 2019.

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