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Before there was a Spain, two half-brothers waged a less-than-chivalrous civil war for control of a powerful Iberian kingdom.

On Aug. 1, 1366, a tri-masted Castilian carrack eased alongside a pier on the Adour River in Bayonne, France. Aboard were Peter I—until five months earlier the king of Castile (encompassing much of present-day Spain)—his daughters and a handful of advisers. The carrack also carried Peter’s personal belongings and a few chests of coin and jewels—the remains of the monarch’s disposable wealth. Deposed by his illegitimate half-brother Henry of Trastámara and deserted by many of his allies, Peter had retreated steadily in the face of the usurper’s
advances and finally fled the peninsula altogether.

Two days after his arrival in Bayonne, Peter—whom detractors disparaged as “Peter the Cruel”—and his entourage traveled north to Capbreton. Riding south from his capital at Bordeaux, Edward—Duke of Aquitaine and England’s Prince of Wales—met Peter with great pomp and embraced him warmly. A contemporary chronicler wrote that Edward pledged to help Peter regain his throne, “even if it cost me my dukedom, and my life to boot.…A bastard never wrought an act of folly as great as this without paying for it at the edge of the sword.” With that the two toasted their alliance with wine served by a chevalier wearing golden spurs.

In Bordeaux, over several days marked by dancing and feasting, Peter plied Edward with flattery and lavish gifts, including a golden table ornamented with rich gems. And he held forth the promise of even greater riches. In return Edward vowed to assemble an army large enough to return Castile to its rightful ruler. It was a pledge that bore consequences neither man foresaw.

Edward’s decision to back Peter’s bid to regain his throne was neither altruistic nor made simply out of obligation to a fellow royal.

Their meeting at Bordeaux came during a lull in the Hundred Years’ War—10 years after Edward’s defeat and capture of French King John II at the Battle of Poitiers, and six years after the Treaty of Brétigny nominally settled the struggle. But the power struggle continued, as proxies on either side sought to maintain or expand their political influence and territory. Among the advantages England may have anticipated from an alliance with Castile was Peter’s help in subduing, or at least distracting, the bands of French-paid mercenaries (routiers) then ravaging the countryside in English-ruled Aquitaine. Castile’s substantial fleet might also tip the naval balance in England’s favor.

By mid-month Charles II of Navarre, whose kingdom lay sandwiched between Aquitaine and Castile, had joined Edward and Peter. Though Charles was widely known to be a fickle, devious and treacherous ruler whose loyalty was never certain, an alliance with him—if it could be maintained—would buffer Aquitaine’s southern flank. But Charles wasn’t the only untrustworthy member of the burgeoning alliance; Peter himself was making promises he could never hope to fulfill. Edward and Charles agreed to foot the campaign expenses in exchange for promised financial compensation and land grants, including lucrative Castilian coastal communities and shipbuilding centers. But in a kingdom riven by factions, Peter couldn’t make such concessions without alienating his subjects and supporters. Unbeknown to his allies, he never intended to repay them.

Peter had other, more obvious shortcomings. Edward’s chief counselors (among them Sir John Chandos, whose herald left a poetic chronicle of the prince’s reign) advised against the alliance, pointing out that Peter’s cruelty and arrogance had initially prompted his overthrow. He was even rumored to have murdered his wife Blanche of Bourbon. Furthermore, Peter had been excommunicated, so any support for him would draw the displeasure of Pope Urban V. But Edward’s dreams of glory and his resolve to defend a fellow royal from the usurpation of one known as “the Bastard” trumped all protestations of caution.

At the time Edward’s hold on Gascony was weakening, thus the prince also relished an excuse to both occupy his subjects and restock his depleted coffers. Initially, however, mounting campaign costs only served to further deplete those coffers. He sold and melted down palace silver plate for coin and even wrote to his father, King Edward III, for a share of the ransom paid thus far by France for John II, who had since died in captivity. In the end Edward raised sufficient funds without having to tax the inhabitants of Aquitaine, which would have left a discontented populace in the prince’s rear.

Gathering the necessary forces was also relatively easy. Numerous English and Gascon knights had joined the ranks of the “free companies,” men who had resorted to pillaging in the time of the treaty. When called to arms by the prince, Sir Hugh Calveley and other such mercenaries flocked to his standard. According to chronicler Jean Froissart, the prince hired some 12,000 of these company troops. Edward also called on his Aquitanian lords to join the expedition with their own contingents and retainers. He assembled the army at Dax, in the foothills of the Pyrenees near Navarre.

Also gathering were rumors the ever-unpredictable Charles of Navarre was contemplating another turn of his coat. In return for land and even more riches than Peter had promised, Charles had reportedly promised Henry he would bar passage of Edward’s army through Navarre. To forestall any such weakening of Charles’ resolve, Edward ordered Calveley to invade Navarre from his camp in northern Castile. Calveley crossed the Ebro River and captured a number of towns in his march toward Charles’ capital city of Pamplona. At this display of force Charles knuckled under, insisting his support of Henry had been insincere and renewing his promise to open the passes into Castile.

On Feb. 14, 1367, the lead elements of Edward’s army set out for Roncesvalles Pass, the gateway to Castile. The prince’s younger brother John of Gaunt, Duke of Lancaster, commanded the vanguard. The 26-year-old had arrived in Bordeaux in early December with between 400 and 500 soldiers, mostly archers. In Brittany a force commanded by Sir Robert Knolles joined the column, as did other such prominent knights as Thomas d’Ufford, William Beauchamp, John Neville and Edward’s counselor Sir John Chandos, the latter perhaps the most experienced knight in the army besides the prince himself.

The main body of the army followed the next day. Included were knights from Normandy, Hainault, Brittany and Gascony, as well as levies from Aquitaine. Estimates number the army at upward of 25,000 men. It was a formidable force for the time, made even more daunting by the roaming bands of free company men, who proceeded to rob and pillage the lands of the duplicitous king of Navarre.

The road to Roncesvalles led across the Nive River and then upward through a narrow gorge. The march was grueling and dangerous, with bitter cold and the ever-present fear of ambush dogging the men of the van. Certainly some must have recalled that six centuries earlier the famed Frankish knight Roland had been ambushed and killed in the same pass.

When Henry learned Edward was on the march, he sent word to Bertrand du Guesclin, a free company leader from Brittany who had helped him seize the throne, imploring him to rally his forces to the defense of Castile. Du Guesclin had earned his laurels fighting for France against England in the opening phase of the Hundred Years’ War and had been awarded a pension by the dauphin (the future Charles V). Having spent several years fighting in various campaigns outside the boundaries of the Treaty of Brétigny, he now returned to help his client keep his throne.

Prince Edward’s intent was to march on the Castilian capital of Burgos. The most direct route through Salvatierra and Vitoria traversed rugged high country that would tax his men and leave them vulnerable to ambush. The alternative route through Logroño on the Ebro was easier to cross but longer. Edward sent a force of 160 foot soldiers and 300 mounted archers under Sir Thomas Felton south through Logroño to scout for Henry’s army, then set out for Salvatierra with the bulk of his army.

Peter implored Edward to sack the town as an example, but its inhabitants yielded without resistance, and the prince kept his army in check as he awaited Felton’s report on Henry’s position. When it came, it was a surprise: The Castilian army had crossed the Ebro and was coming on. Edward was reportedly impressed by Henry’s boldness and glad the usurper appeared to desire battle.

Perhaps Edward was eager to do battle, but he first made an attempt to dissuade Henry from the fight. The prince sent a message by herald to the Castilian camp, offering to mediate between the half-brothers and extending honorable terms in return for Henry’s renunciation of his claim on Castile. The offer fell on deaf ears; as a reigning king and son of another, Henry had no intention of abdicating. The armies closed on Vitoria.

On reaching Vitoria and anticipating attack, Edward deployed his army in order of battle, its thousands of banners soon fluttering in the stiff March breeze. But the Castilians already occupied a strong position in the hills and chose not to make a frontal assault, electing instead to harass Edward’s exposed and vulnerable force with pinprick raids. One destroyed a detachment under Calveley, after which the Castilians raided Lancaster’s camp and surprised Felton’s scouts, killing or capturing them all. Edward’s subordinates, including Chandos, advised the prince not to read too much into these early losses, insisting that Henry’s army, though more than twice the size of Edward’s force, would lose decisively when it joined combat with the flower of the English army.

After seizing the throne of Castile, Henry exploited the ongoing power struggle between England and France to secure military aid from Bertand du Guesclin, a French mercenary leader. (Prisma Archives)

With Henry commanding the heights and the dismal March weather taking a toll on Edward’s men and horses, the prince changed tactics. He broke camp and abandoned the direct road, crossing the Ebro at Logroño and gaining the road to Burgos that passed through the towns of Nájera and Santo Domingo. The maneuver obliged Henry to come down from the hills to protect Burgos. Recrossing the Ebro, he hurried to Nájera to interpose his army between the prince and the capital, anchoring his defensive line be-
hind the rain-swollen Najerilla River. The terrain otherwise offered the Castilians little defensive cover.

Having faced Edward in battle before, most of Henry’s military commanders advised their sovereign not to attack. Du Guesclin urged him to further strengthen his defensive position by digging ditches and using the army’s wagons as bulwarks. While the Castilians were well supplied from Burgos, he noted, the English were backed up against mountains bare of forage. Within days du Guesclin argued, famine would force Edward’s army to retreat “like a stag from a dog.” Were the prince to attack, he added, so much the better, as Henry’s formidable defensive line would stop him cold.

Henry knew du Guesclin’s advice was sound, but it was also politically impossible. With his half-brother Peter advancing on the capital at the head of a large army, Henry was fast losing face. Many nobles of Burgos had already deserted his cause, largely due to his inability to reward them satisfactorily after the usurpation. Were Henry to waver, the principal nobles would switch their allegiance to Peter. Henry must show both a willingness to fight and confidence that God would reward his cause with victory.

The grassy plain separating the two armies rose gently toward the English encampment at Navarette. Henry’s best chance for victory was to force the English to attack him across the Najerilla and not risk his army in an uphill advance. But much of his force comprised light cavalry, which performed best on open ground and would be wasted in defense behind a river. So, against du Guesclin’s best counsel, during the night of April 2–3 Henry’s army crossed the Najerilla and encamped on the far bank. At dawn it advanced, with du Guesclin’s men in the vanguard.

Henry’s army consisted of three divisions. The first was the French contingent under du Guesclin and Marshal Arnoul d’Audrehem, supported by many of the Castilian nobility, including Henry’s younger brother Don Sancho. Joining them was the military order of Alfonso XI, the Knights of the Band—named for the red sashes its members wore and comprising some 1,000 foot soldiers flanked by cavalry. The second division comprised a core of 1,500 knights under Henry’s direct command, two wings of mounted men-at-arms and assorted units of crossbowmen, slingers and lightly armed horsemen. A division of mixed levies brought up the rear.

When told of Henry’s advance, a delighted Edward exclaimed, “By St. George, this bastard is a valiant knight!” The prince immediately ordered his army forward, the troops descending from the high ground of Navarette. They moved in tight columns with banners flying and their shields emblazoned with the emblem of St. George, a red cross on a white field. Edward’s army, too, comprised three divisions. The Duke of Lancaster commanded the first. The prince himself led the second, with Peter at his side. Heading the third was John, Count of Armagnac, with other Gascon nobles. Even as the armies readied for combat, batches of free company men deserted Henry’s line, dashing across the plain to swell Edward’s ranks.

The usurper sent du Guesclin forward on foot to meet Lancaster head-on. As the men of both vanguards advanced, English archers on the wings loosed their arrows into the Castilian horse, and Henry’s slingers responded in kind. The reinforced armor worn by du Guesclin’s men initially blunted the penetrating power of the fearsome English longbows, and many of the bowmen themselves succumbed to the hail of Castilian sling stones. But the relentless rain of English arrows soon reduced the slingers, and they ceased to be a factor in the battle.

After the initial clash, the opposing men-at-arms threw aside their lances and hacked into each other with battle axes, swords and daggers. Bloody hand-to-hand combat raged, and for a time it seemed the Castilians had the upper hand, as the English slowly gave ground. But at that point Armagnac’s Gascon knights charged into the fray, and at the sight Henry’s left wing, led by Don Tello, fled without striking a blow. Pressing his advantage, Armagnac immediately pivoted his formation and tore into du Guesclin’s left flank and rear. With Edward stiffening the center, du Guesclin’s division was virtually surrounded.

No longer was the battle a melee of parallel ranks hacking away at each other. It was instead a compact ring, bristling with spears, two-handed swords and double-edged axes, an ever-narrowing noose that constricted around the Castilian vanguard. Seeing the difficulty du Guesclin was in, and realizing the tide of the battle depended on his relief, Henry repeatedly attempted to break the circle from without.

At that critical juncture the fall of Henry’s royal standard sparked a panic among his forces. The Castilian horse fled the field, and after a final attempt to free du Guesclin, Henry followed. Many of his knights fought on, desperately seeking an escape, but the bulk of the usurper’s army was soon in headlong flight toward the Najerilla, its panicked men pursued by vengeful English and Gascon riders who slaughtered many on the plain and in the bottleneck of Castilians trying to cross the sole narrow span across the river.

Du Guesclin, his vanguard cut off and losing men at every sword stroke, could no longer hold out. After ignoring a first appeal to surrender, du Guesclin heeded the second issued by Edward himself. Peter, witnessing the capitulation, asked for the prisoners to be delivered up to him, but Edward was all too aware of his ally’s sanguinary disposition and refused. Peter then rode out across the field strewn with dead and wounded, crying out for the “son of a whore who calls himself king of Castile!”

The day after the battle Peter encountered a Gascon knight leading a captive. Recognizing the prisoner as a courtier who had gone over to Henry, Peter killed the man on the spot, angering the knight as well as Edward when told of the incident. It was an early sign of the bad blood that would doom their alliance within a few short months.

Peter’s renewed reign was destined to be brief.

Edward, falling ill and disgusted by his erstwhile ally’s continued cruelty, arrogance and failure to honor his debts, soon returned to France. Though he had little to show for his outlay of money, men and materiel, Edward did bring with him a 170-carat ruby, extracted from Peter in partial payment, that remains the centerpiece of Britain’s imperial state crown.

From exile in France, Henry soon raised a new army with the ransomed du Guesclin and resumed the long and bitter civil war. In March 1369 he caught up to Peter at Montiel, in southeastern Castile, and for the last time defeated his half-brother, who holed up in the city fortress. A desperate Peter sent a courier to bribe du Guesclin, promising Henry’s confidante money and land if he would switch his allegiance. Lured from the castle ostensibly to seal the deal, Peter was assassinated, reportedly at his brother’s own hand.

Not all of the Englishmen who fought Henry were done with Castile, however. In 1371 Edward’s brother John of Gaunt, Duke of Lancaster, married Peter’s daughter Constance of Castile and through her claimed the throne, albeit from a safe distance in London. When Henry died in 1379, his son John succeeded him, but all the while Lancaster was spinning schemes to take the kingdom by force. In 1386 John launched an ultimately failed expedition to Castile and renounced his claim to the throne two years later. Before doing so, however, he married his daughter Catherine to the young nobleman who eventually became King Henry III of Castile, which—in one of history’s great ironies—rejoined the lines of contentious half-brothers Peter and Henry. 

Kentucky-based bookseller and freelance writer Douglas Sterling is a contributor to several HistoryNet magazines. For further reading he recommends Pedro the Cruel of Castile, 1350–1369, by Clara Estow; The Life of Edward the Black Prince 1330–1376, by Henry Dwight Sedgwick; and Bertrand of Brittany: A Biography of Messire du Guesclin, by Roger Vercel.