Brother vs brother in 15th-century Castile: The Battle of Olmedo in 1467

By Javier García de Gabiola

During the mid-fifteenth century, the Kingdom of Castile was involved in a bloody set of three large battles to determine whether its king would prevail over the nobles in a kind of Spanish Wars of the Roses. The second of these battles was Olmedo, in 1467. There, Enrique IV, malignantly called “the Impotent,” fought his fourteen-year-old half-brother Alfonso. Scholars have previously simply described the battle as a confused fight and nobody has made a serious effort to narrate it. But we have at least two different chronicles, one for each side of the battle. They tell us the story in detail, blow by blow, allowing us to reconstruct the events at Olmedo.

“To the ground, bitch!” – with these words Diego Lopez de Stúñiga, Count of Miranda, tore down a statue of King Enrique IV of Castile on 5 June 1465 before the populace. That was the end of a crude ceremony known as the Farce of Ávila. During this act Alfonso Carrillo, Archbishop of Toledo, read a proclamation in which the king was disparaged as a friend of the Moors and as effeminate. It was also claimed that his daughter Juana, the presumptive heiress, was not his, but the child of Beltrán de la Cueva (thus, Juana has passed into history as “la Beltraneja”). Then the rebel nobles proceeded to proclaim Prince Alfonso as their new king.


The main instigator of the Farce of Avila was Juan Pacheco, Marquis of Villena, who had been the tutor of King Enrique while he was a child. Pacheco, a very capable man, had masterfully directed the government of Castile during the early years of Enrique’s reign, but he lost his position with the appearance of the new favorite, Beltrán. Then Pacheco, slippery and tortuous, a warrior who looked like a priest, forged an alliance with a priest who looked like a warrior, the fierce Archbishop of Toledo.

Enrique IV of Castile depicted in a 15th-century manuscript – Wikimedia Commons

The war began with occasional sieges and maneuvers until the situation intensified in August 1467. In the important town of Medina del Campo, the loyal citizens had raised breastworks to prevent the rebel knights from exiting La Mota Castle. However, the militias were being hard-pressed by the knights, so they called upon King Enrique for help. Hurrying to their aid, Enrique left Segovia, then the capital of the kingdom, with his allies the Mendoza clan, led by the Marquis of Santillana, and his favorite, Beltrán de la Cueva. In Cuéllar, a city 65 kilometers to the north, they were joined by the retinues of Pedro Velasco. He was originally one of the supporters of the rebel prince Alfonso, but had returned to the king’s side. Enrique’s army numbered about 4,000 men, made up of 1,430–1,700 cavalry (of which 800 were knights in full armor) and 2,550 footmen.


In front of them, Prince Alfonso’s troops were concentrated in Olmedo, a village located west of Cuéllar that blocked the road to Medina del Campo. There, Alfonso’s army was as yet not at its full strength, since his main ally, Pacheco, was still in Toledo. Thus, the prince had only 800 horses of the Stúñiga clan, the Count of Luna, the Archbishop of Toledo, plus a troop from Pacheco, under Garcia de Padilla. News of this came to King Enrique, who, pressed by Santillana, decided to march to Medina del Campo passing in front of Olmedo because he thought that the rebels would not dare to intercept him.

The royalists were not aware, however, that within a few days Alfonso’s army would be reinforced, raising their numbers to about 2,000 men, made up of 1,350–1,550 cavalry (of which 400 were knights) and about 500 footmen. Where it mattered, both sides were evenly matched, because the infantrymen were made up of citizen militias, who consisted of crossbowmen and spearmen who had no other function than to protect the camp or for siege works. Enrique had twice as many knights as Alfonso, but had one-third less jinetes. The jinetes were light cavalry with half armor and iron hats, who could fight as heavy cavalry, but being lightly armed, agile, and fast, were more suited to harassing the enemy by throwing javelins.

Opening moves

King Enrique and his troops left Cuéllar on 18 August for Olmedo, only to find two days later that the rebels were blocking his march. Alfonso’s forces were arranged this way: on the right battle was Padilla, with Pacheco’s troops, some 200-400 jinetes in all; then it followed the central battle of the Archbishop of Toledo, the leader of the rebel army, with a squadron of heavy cavalry under his personal command of 120 men-at-arms, and to his left, another squadron of 250 jinetes under his bastard, Troilo Carrillo. Behind them it was the rearguard of the Stúñiga clan, consisting of 150 knights under the Count of Plasencia, escorted by two squadrons of 200 or 250 jinetes of the Countess of Belalcázar and the Count of Siruela, under Pedro de Hontiveros and the Count of Ribadeo. Among them they were probably also included 80 horsemen of the Count of Miranda. Finally, there was the battle of the left, with a squadron under Fonseca with 130 knights, and then a squadron of 250 jinetes under Enríquez and the Count of Luna. Because Prince Alfonso was just a kid, he rested in the monastery of Santo Domingo, near Olmedo, accompanied by the knights less fit for war.

Coin of Alfonso – photo by Numismática Pliego / Wikimedia Commons

The left flank of King Enrique’s army was formed from troops of the Mendoza clan. First, the 300 jinetes under Galindo; then 200 knights under Marquis of Santillana; and finally, 150 jinetes under Pedro González de Mendoza, Bishop of Calahorra, and Juan de Mendoza. The center of the army was placed under Pedro Velasco, and was formed into three squadrons: on the left 80 knights under Juan de Velasco, Lord of Siruela; then 320 knights of Pedro Velasco; and on his right, the brothers Luis and Sancho Velasco with 300 jinetes. Finally, there was the right wing, under Beltrán de la Cueva, with 150 knights, flanked by other 200 jinetes under another Velasco. Behind, it was King Enrique with an escort of less than thirty horsemen, and even further in the rear, guarding the camp, the footmen.


After some unsuccessful attempts to avoid the battle, the squadrons began their advance against each other in what was to be a solely cavalry battle. The sound of hooves hitting the ground joined the neighing of horses, and the cavalry, firstly marching forward, then accelerating the trot, and finally at full gallop with the spears pointing forward, clashed with their enemies.

With the armour shining under the August mid-day light, the loyal Mendozas´ left flank under the Marquis of Santillana hit on Padilla´s rebel right flank, pushing it backwards and taking his flag. However, the royalist flanks, under Galindo and Juan de Mendoza, formed by jinetes were in turn defeated by the rebel horsemen and ended up fleeing and losing two banners. The rebels, more agile and faster than the heavy cavalry of Santillana´s main squadron, probably evaded him and turned to his flanks to disperse the loyalists jinetes. In any case, Santillana held his squadron and then, as we will see, he would make the brightest action of the battle as he crossed the entire field to aid Beltrán de la Cueva’s battle. To do this, Santillana had to leave his sector of the battlefield, a fact that probably caused the wrong impression to a pro-Alfonso chronicler that he had been defeated.

Rebels killed and captured

Meanwhile, on the opposite right wing, the loyalists were being destroyed. All started with a frontal clash between the two rival wings of cavalry: the rebels Fonseca and Enríquez charged against Beltrán de la Cueva. Once the spears were broken in the initial clash, the knights drew their swords and continued to fight. The rebels began to push Beltrán´s troop, who lost a banner. In fact, the king’s favorite was hit by several enemy knights who surrounded him, and he was about to be killed or captured. However, Beltrán was an exceptional rider, and despite having his reins cut, losing his spurs and his horse´s bit, he managed to survive. Even more, Beltrán went into personal combat with Fonseca, and “hit him with the tip of the sword, which came between the bevor and the sallet, that mortally wounded him. ” At the end Fonseca lost his helmet, was wounded twice and after losing two other knights of his entourage had to leave the battle, only to die a few days later.


In the meantime, as we said, on the other flank, Santillana managed to control his squadron of heavy cavalry, which says a lot about his leadership abilities at a time when knights used to disperse after the first charge and rarely returned to the field. He crossed the battlefield from north to south, passing through the center, which had been empty of troops of both sides as we shall see, until reaching where Beltrán was, to assist him and saving the day. While Beltrán was still fighting, the rebel Enriquez managed to disperse the royalists jinetes, but on returning to the battlefield, exhausted, he ran into the heavy cavalry squadrons of Beltrán and Santillana who captured him. Thus, Santillana´s maneuver was undoubtedly the most important and decisive tactical action of the whole battle, which is barely narrated (and not clearly) by only one of the two chroniclers.

The struggle over the centre was the most confusing of all. The clash started, we do not know whether spontaneously or planned, when the loyalist squadron under Pedro Velasco was surpassed from his left by the squadron of his cousin Juan Velasco to charge at the vanguard, forming a wedge of heavy cavalry that impacted on the rebel knights of the Archbishop of Toledo, breaking through the other side of the rebel squadron. In the attack, Juan Velasco took an enemy banner, and the Archbishop himself received a spear hit that pierced his left arm from side to side, although the prelate hid his injury and continued the fight. However, Juan Velasco, surprised by his own success, not knowing that behind him was also charging his cousin Pedro, fearing being caught between the troops of the Archbishop and the battle of Stúñiga still in front of him, left the battlefield.

Meanwhile, Pedro Velasco carried on the attack with his larger heavy cavalry squadron following his cousin, pushing the reorganized battle of the Archbishop against the rear, mixing it with Stúñiga´s troops and cornering the rebels against the city of Olmedo. In the attack Velasco took two of the banners of Stúñiga, so he reached the rear of the rebels. With this charge Velasco cleared the troops around the center of the battlefield, which allowed, as we saw, the movement of Santillana to save Beltrán de la Cueva. Meanwhile, the rebel jinetes under Hontiveros and the Count of Ribadeo, taking advantage of the gaps left by the loyalists, charged against the jinetes of Sancho and Luis de Velasco, dispersing them and taking a banner. After that, the rebels continued their ride to sack the camp of the king. The footmen fled when they saw the horsemen coming, so the rebels ransacked the baggage taking a royal flag. However, when Hontiveros returned to the field, with his horsemen tired and dispersed, he was easily captured by Pedro Velasco’s intact heavy cavalry squadron.

Who won?

The end of the battle was somewhat comic, as both the pretender and the monarch fled from the field before knowing the outcome of the battle. Enrique was told by his own chronicler Enriquez del Castillo, who was present at the battle, that he had won. The king then sent the chronicler to Medina del Campo to report the victory and to prepare accommodation for the night for all the army. When Enrique with his troops arrived they were greeted by the cheers of the populace by torchlight.


Thus, the objective of the king had been fulfilled and Medina del Campo had been saved. But who really won? Chroniclers representing each side said both claimed their own forces were the winners as they stayed on the battlefield – in fact, half of the royalists and two-thirds of the rebels had fled. From both reports we may deduce that the rebels lost their wings. The center under the Archbishop was still there, but it was cornered against Olmedo. Because the king’s troops departed for Medina del Campo, Prince Alfonso’s warriors controlled the battlefield in the end, but they were not able to prevent the saving of the village by Enrique. Fonseca was dead, Enríquez and Hontiveros had been captured, and the Archbishop was severely wounded, so it seems that the rebels suffered more than the royalists.

Queen Isabella I of Castile – portrait from the 15th or 16th century.

Both sides continued to receive reinforcements, with the loyalists in Medina del Campo growing to 2,000 horses and 4,000 footmen, but in Olmedo the rebels received up to 3,340 horsemen under Pacheco himself. Instead of attacking the king, Pacheco marched south to Segovia, where the gates were opened for the rebels, allowing them to capture the royal treasury. It seemed as if the rebellion might have been successful – however, in another twist of fate, Prince Alfonso died in 1468 (with one chronicler suggesting that he was poisoned by Pacheco himself). His crown was left to his sister, Isabella, and she was asked to take her brother’s place as the champion of the rebels. However, she refused, and went into negotiations with Enrique. Ultimately, he agreed to recognize Isabella as his official heir instead of his daughter Juana, and with the king’s death in 1474, Isabella I would come to the throne, establishing a reign that would see the unification of Spain and its rise into a global power.

Javier García de Gabiola lives in Madrid, where he works as a lawyer and historian of military warfare, having published some fifty works in Spanish magazines, as well as writing for Helion and the Autónoma University of Mexico.

This article was first published in Medieval Warfare. Now called, Medieval World: Culture & Conflict, you can get the magazine through the Karwansaray website or by becoming a patron on our Patreon page.

Top Image: Battle scene from the Prayerbook of Alphonso V of Aragon, British Library MS Additional 28962 fol. 78r