The Most Dramatic Moment of the Middle Ages!

An evil king versus a good king. They are half-brothers. It’s a fight to the death in a tent!

The Middle Ages had its share of dramatic moments with excitement and historical importance. However, what happened on the 23rd of March, 1369, has a truly epic quality to it.


The events of that day can be traced back to the reign of Alfonso XI, King of Castile (1312-1350). Alfonso was a strong ruler who expanded his kingdom. However, he had one failing: he was married to one woman while he loved another. Alfonso had been married to Maria of Portugal in 1328, but at the same time had met a Castilian noblewoman named Leonor de Guzman. He greatly preferred Leonor, who by all accounts was a capable lady, and together they had 10 children. Meanwhile, once Queen Maria bore him a son, Pedro, in 1334, she and her son were sent to live away from the royal court. The scandal and the exile would leave great bitterness in both Maria and Pedro.

Alfonso XI died in 1350, a victim of the Black Death, and Pedro became the new King of Castile, under the guidance of his mother. Over the next several years the royal court was the scene of much intrigue, as the new king had to deal with Leonor and her two twin sons Enrique and Fadrqiue, who had amassed much wealth and power. The nobles of the realm were involved in political games and scheming too.


At the heart of these intrigues was Pedro. Physically he was blond and blue-eyed, tall but thin, and had a slight speech impediment. He liked to ride horses, hunt and take part in jousts. However, his personality is the reason Pedro was nicknamed ‘the Cruel’. L.J. Andrew Villalon sums up the Castilian king this way:

From early in Pedro’s reign, it became clear to friend and foe alike that the monarch had a suspicious and vindictive personality. He employed deceit and cruelty wherever he encountered opposition, real or imagined. His unforgiving nature, combined with a very long memory, made it very hazardous for an opponent to attempt reconciliation with the king. Time and again, the aristocracy looked on as one of its members thought he had made peace with the king, only to be executed or assassinated when the opportunity arose…a modern psychiatrist could scarcely avoid a diagnosis of progressive paranoia, aggravated by homicidal rage and sadistic tendencies.

One of Pedro’s first victims was his father’s mistress Leonor. Soon after he came to the throne Leonor was imprisoned, and on his mother’s orders she was executed in 1351. Meanwhile, the nobility and even his chief advisors were not safe from Pedro’s wrath. If he suspected their loyalty, or if they failed him in some way, he would be quick to send the executioners. One man, who had been a member of the King’s inner circle for ten years, was seized and beheaded. He was allowed to write one letter back to Pedro, where he says:

Now at the moment of death, I give you my final counsel – if you do not put aside the dagger, if you do not stop committing such murders, then you shall lose your realm and place your person in the greatest jeopardy.


Pedro seemed to have inherited another flaw from his father – he loved his mistress more than his wife. In 1352, he met a Castilian noblewoman named María de Padilla and seems to have instantly fallen for her. This petite, dark-haired beauty was his constant companion and chroniclers have praised her as being a moderating influence on Pedro, counselling him to be merciful to his subjects.

However, at his mother’s insistence, he was arranged to be married to Blanche of Bourbon, the daughter of the Duke of Bourbon – it would solidify an alliance with France and deliver to Pedro a huge dowry. The wedding took place amongst much pomp and ceremony on June 3, 1353 – two days later Pedro abandoned his new bride and went back to María. This created a massive scandal throughout Europe, alienating both France and the Papacy. The King would spend just two more nights with his French wife, and after trying to get an annulment, he had her imprisoned and then murdered in 1361.

Iberia in 1360

To add to Pedro’s tyrannical behaviour at home was his belligerent foreign policy. While most of his predecessors had Castile direct its energies against the Muslims of Granda, Pedro allied himself with Granada and decided to invade his fellow Christian kingdom of Aragon. He simply wanted to take control of the Iberian peninsula at the expense of the Aragonese ruler Pere III. From 1356 to 1366, the two kingdoms fought against each other, trading castles and land along the border.


In 1358, Pedro invited his half-brother Fadrique to dinner with him at his palace in Seville. After he got there Fadrique learned something was amiss, but before he could escape the guards escorted him to the King’s dinner table. There Pedro ordered his execution, and a man came up behind Fadrique and smashed his skull with a mace. Pedro then went out through the palace, slaughtering members of his half-brother’s entourage, before returning to his dinner table. Upon returning he noticed that Fadrique was still alive, the king handed over a dagger to a young page to give the final blow. In the words of one chronicler, “after this was done, the King sat down to eat where the master lay dead.”

This brutal act pushed Fadrique’s twin brother Enrique to make a deal with Pere III – the Aragonese would support his bid to overthrow Pedro and become the new King of Castile. Soon the nobles of the country flocked to Enrique’s banner. The war would also drag in England and France, setting up Iberia as another theatre in the Hundred Years War.

By 1366 Enrique had forced Pedro to abandon his kingdom, but the Castilian king was not finished yet. He made a deal with the English and Edward the Black Prince came to the Iberian Peninsula. On April 3, 1367, an English army of 28,000 men defeated a Castilian-French force at the Battle of Najera. Enrique and a few others were able to escape, but many of his fellow Castilians were captured. However, at this moment of victory, Pedro could not hold back his hatred and desire for revenge – he saw one of his former followers among the prisoners, and in a fit of rage took out a knife and stabbed him to death. When the English prince upbraided him for his unchivalrous and unprofitable conduct, Pedro replied that he would pay the ransom for every captive. Edward refused such an idea, saying “even if Pedro offered a thousand times what each prisoner was worth, he would not surrender any of them in as much as he believed the king was paying to kill them.”

Within months the alliance with England was over – Pedro, who was also notoriously greedy, delayed in sending the Black Prince the gold he had promised for supporting him regain his throne. As the English left, the men of Castile returned to Enrique’s side. He also got the assistance of Bertrand du Guesclin, a French knight and military commander who was one of the leaders of the ‘Free Companies’ of mercenaries.


By 1369 the war was going badly for Pedro – cities and castles were falling to Enrique’s forces. Then, on March 13, 1369, Pedro and his army were ambushed and defeated by Enrique and Guesclin, forcing the Castilian monarch to seek safety in the castle of Montiel. The castle was besieged and within a few days the provisions and water were running out for the defenders.

Pedro soon came up with an idea to get him out of this trap. He sent a knight who knew Bertrand du Guesclin over to the French camp in the middle of the night – he met with Bertrand and made him an offer: if he would allow Pedro to escape, the Castilian ruler would make him lord of six towns and give him 200,000 gold doubles. He even added that the French knight should do this, “for the honour you will have in helping such a great king, when the world will know that it is by your hand that he recovered his life and his realm.”

Bertrand was somewhat dubious of the offer, but he agreed to consider it. The next day Pedro got word that the deal was accepted, and on the night of March 23rd, he and a small entourage snuck out of Montiel and went to the French camp. Pedro went to Bertrand’s tent, but he wanted to get away as fast as he could. One of Bertrand’s men told him to “Wait a moment” and soon another visitor arrived: Enrique.

Only then did Pedro realize he had been betrayed. Bertrand had earlier gone to Enrique and told him of the offer. Enrique responded by saying he would match the bribe, but only if the French knight agreed to lure the Castilian king out of the castle and into Enrique’s hands.

France, Besançon, Municipal Library, Ms. 864 f. 286v

It was inside this tent that two half-brothers met – for years they had schemed and fought against each other. Pedro had murdered Enrique’s twin brother and other family members. Now he would be able to get his revenge.

What happened next differs depending on which chronicle you read. The best informed would likely have been to the Castilian chronicler Pero López de Ayala, who wrote:

As soon as he went in, King Enrique caught hold of King Pedro but did not recognize him; it had been a long time since he had last seen him. It is claimed that one of Monsieur Bertrand’s knights said to him, “Look, this your enemy!'” King Enrique was still in doubt as to whether it was indeed him, but men say that King Pedro then exclaimed, “It is me! It is me!” At that point King Enrique recognized him and struck him with a dagger across the face. It is said that the two of them, King Enrique and King Pedro, fell to the ground, and as they struggled there King Enrique stuck his adversary more blows.

In another version given by the chronicler Jean Froissart, Enrique came into the tent saying, “Where is the son of a Jew whore who calls himself king of Castile?” Pedro answered, “You are the son of a whore, for I am the son of the good King Alfonso!”

They both pulled out weapons and lunged at each other. Soon they were wrestling on the ground, with the fate of Castile hanging in the balance. According to some accounts, it seemed that Pedro was about to win, but someone pulled him off of Enrique. No one came to Pedro’s assistance. Finally, in the words of Froissart, “Enrique thrust a sword in his brother’s belly and killed him.”

With the fight now finished, Enrique ordered his men to behead Pedro, while his body was left outside the tent for the next few days where it would be subject to more abuse. Enrique II was now the undisputed ruler of Castile – he would reign for ten more years. While the Aragonese king Pere III was upset that Enrique would not keep his promises in exchange for his help in gaining the throne, the two did have their children marry each other, a union which would eventually lead to the unification of Aragon and Castile into Spain in the 15th century.

Meanwhile, Bertrand du Guesclin would get his reward of six towns and 200,000 gold doubles, but he did not enjoy it long. In 1370 the French king recalled him back to his country, where he made Bertrand the commander of his military. Over the next ten years he would reconquer much of France that was in English hands, solidifying his legacy as one of the best military commanders of the Middle Ages.

As for Pedro, his reputation was not improved by the chroniclers of his time. He did have supporters, and in some circles he went by the nickname ‘the Just’. However, likely, he will forever be remembered as one of the greatest villains of the Middle Ages. Here is how his modern biographer, Clara Estow, sums up Pedro the Cruel:

He was raised at the age of sixteen to the most exalted post in the kingdom and, for the next twenty years, he did not enjoy more than a few moments of pleasure or peace. That many of his troubles were of his own design only makes his story more tragic than pathetic.

dramatic moment middle ages

Further Readings:

Clara Estow, Pedro the Cruel of Castile, 1350-1369 (Brill, 1995)

Mary Hillgarth (trans,) Pere III of Catalonia: Chronicle (Pontifical Institute of Mediaeval Studies, 1980)

Peter Such (trans), Chronicle of King Pedro (Liverpool University Press, 2020)

Richard Vernier, The Flower of Chivalry: Bertrand du Guesclin and the Hundred Years War (D.S. Brewer, 2003)

L.J. Andrew Villalon, “Spanish Involvement in the Hundred Years War and the Battle of Najera,” The Hundred Years War: A Wider Focus, eds. L.J. Andrew Villalon and Donald J. Kagay (Brill, 2005)

L.J. Andrew Villalon, “Pedro the Cruel: Portrait of a Royal Failure,” Medieval Iberia: Essays on the History and Literature of Medieval Spain, eds. Donald J. Kagay and Joseph T. Snow (Peter Lang, 1997)