The Gold Rose: An Edward of Angoulême timeline

Great to see the complete Plantagenet family tree!
Thanks. The trees will be a little bare at first, but they will branch out as the timeline moves forward.

For those who missed it, I'll be doing a bit of housekeeping on what's been posted so far.

Has Richard of Bordeaux gotten any titles yet, or are they coming out later?
Not yet, though Gaunt and Joan found a rather remarkable heiress for him in "Parliament of 1379." More to come on that in the future.
Gloucester's chevauchée of 1380
Gloucester's chevauchée of 1380
The Nantes campaign, better known as Gloucester's chevauchée, was a large-scale mounted raid through northern France that culminated in the Siege of Nantes. Carried out by English forces under the command of Thomas of Woodstock, 1st duke of Gloucester, the campaign ran from 5 July to 21 November 1380, near the end of the Caroline War.

King Charles V of France rejected the Treaty of Brétigny and reopened the Hundred Years War in 1369. The war proceeded badly for the English. The French reconquered nearly all of the lands lost in the Edwardian War by the mid 1370s. French victory seemed imminent, but the English managed to negotiate a truce in 1375. Hostilities resumed in 1377 and the two kingdoms fought each other to a stalemate until 1379, when rebellions in Brittany and Languedoc allowed the English to gain the upper hand. Believing that France was near total defeat as Flanders also broke into revolt, the English planned a two-prong assault to force an end to the war.

Preparations for war
Leaders in both England and France had personal stakes in the campaigns of 1380 and deeply involved themselves in war preparations. John of Gaunt, 1st duke of Lancaster and lord regent of England, had taken a renewed interest in his claim to the Castilian throne. The death of King Enrique II of Castile and English alliances with Navarre and Portugal had transformed Gaunt's claim from a technicality into a serious strategic threat to the Trastámaran regime. The English needed to score a quick victory in the north of France if they were to shift resources to southern France and Castile in the long run, as Gaunt intended.

Charles V had a more morbid concern. Charles had been sickly since youth and he'd been plagued by serious health issues since he was poisoned in a failed assassination attempt in 1359. A downturn in his health had inclined him to support a truce with England in 1375 so that his young son would not inherit an active war. Charles eventually recovered, but declined again in 1378. It was clear by 1380 that the king was dying. Charles again looked to pause hostilities for the sake of his son and heir, who was just 11, but English gains in 1379 put France in a weak negotiating position. The French thus needed to inflict fresh pain on the English before seeking talks.

On 6 January 1380, a great council met at Westminster Palace to plan operations for the coming year. The crown's ambitious agenda quickly ran into problems. The campaigns in northern and southern France had to compete both with each other and with a reinvestment in the declining lordship of Ireland for the kingdom's limited shipping resources. Tough choices had to be made.

The southern campaign was given top priority. A Castilian invasion of Navarre was expected in the spring, which gave England little time to act. Navarre's fall would open the western passages through the Pyrenees to France's primary ally, exposing Gascony to attack from the south. Writs were issued for the mustering of men and requisitioning of ships. The army was to embark in mid April and the fleet would return from Bayonne bolstered by larger vessels that overwintered there.

The embarkation date for the northern campaign was set for late May. An army of 3,500 was to sail from Southampton to Cherbourg, lay waste to northern France, then attack the fortified harbor of Le Crotoy, which sat at the mouth of the Somme. Control of Le Crotoy would put the English in a position to threaten the wealthy town of Amiens.

Thomas of Woodstock, 1st earl of Buckingham, was appointed to lead the Le Crotoy campaign. He was not an ideal choice. Buckingham had little command experience. He and the earl of Salisbury had been named co-leaders of a planned offensive in Brittany in 1378, but logistical issues left Buckingham at the head of a small force in Brest while Salisbury led the bulk of the army to capture Saint-Malo. Buckingham extended English control over much of western Brittany following the Revolt of the Breton League, but this was more the result of the confused political situation in Brittany than it was Buckingham's leadership. The young earl, however, did not see it that way and was convinced of his own talent as a commander.

Despite his inexperience, Buckingham was practically the only option. English forces were stretched more thinly than they had been at any time since the dark days of the early Edwardian War. Gaunt, as lord regent, was needed in England at such a time. The duke of Aumale was an affable, but incompetent man and would not be entrusted with campaign leadership unless no other option remained. The earl of March was to lead the campaign in Ireland.

There was no better option outside of the royal family. The earl of Suffolk was a towering figure, but an old man. The earl of Salisbury was a distinguished veteran, but was now in his 50s and planning his retirement. The earl of Stafford had joined the royal council to help the administration of finances. The earl of Warwick had agreed to join the campaign to Ireland for a short time to inspect the state of the lordship. The earl of Devon had no military experience at all, having only recently come of age. The earls of Oxford and Pembroke were both still minors.

King Edward V of England was delighted that his uncle Buckingham had the command, regardless of how the appointment had come about. Edward was especially close to his youngest uncle. Buckingham was 25, only 10 years older than Edward and closer to him in age than either of the king's half-brothers. The stories of Buckingham's Breton campaign, in which he and his men were greeted as liberators in towns once hostile to the English, delighted Edward. The young king had only known the failure of English arms in his lifetime and Buckingham must have seemed to be a great knight and a singularly talented leader for having taken control of so much territory so quickly. At 15, Edward could be forgiven for not appreciating the unique political circumstances that led to Buckingham's success.

On 16 January, Edward made Buckingham the duke of Gloucester, a rank more befitting the king's favorite uncle. The new duke was to be supported by some of the most experienced fighting men in England on the coming campaign. The imposing roster of captains included Sir Hugh Calveley, Sir John Harleston, and Sir Robert Knolles.

As the English met at Westminster in early 1380, Charles V's plans were already in motion.

On 21 November 1379, Charles gathered his most trusted advisors in a conseil étroit to map out the French response to the various crises they faced. The ongoing tax revolt in Languedoc became the council's top priority. The crown was under severe financial stress and revenues were badly needed, but the revolt threatened to spiral into a broader popular uprising if taxes were levied again. Charles took a carrot-and-stick approach to the situation.

On 20 January 1380, Louis I, duke of Anjou, led an army of 1,500 men into Montpellier and declared the city's population guilty of treason for the nonpayment of taxes and violence against the king's tax collectors. Mass executions were ordered. The people threw themselves at Anjou's mercy, pleading for their lives. Only at the last minute, in a carefully choreographed ceremony, did Anjou commute the city's sentence to an enormous fine.

On 15 February, crown officials began fanning out across the region to deliver notices that the king was canceling the most objectionable taxes and that other taxes would be reduced by as much as half. The new, less oppressive tax system, combined with terror Anjou had inflicted on the population, brought Languedoc back under control. The crown raised 120,000 francs in fines by spring, easing the financial strain it was under.

In early March, Charles finally turned his attention to the revolt of Ghent, which had by then both grown to include nearly all of Flanders and had also technically ended. Philippe II, duke of Burgundy, had brokered a peace between Louis II, count of Flanders, and the rebel cities and towns months earlier. The demands of the rebels were met in full, but Louis had no intention of honoring the deal. The nobility of Flanders had spent months preparing for a violent crackdown on the towns.

Charles wanted no part in the civil war that Louis was planning to wage. Louis had maintained a de facto neutrality in the war between England and France for decades, and Charles was glad to leave Louis to his fate now. Louis was fed concerns that direct intervention by the French crown would drive the rebels into the arms of the English, which the count knew would only worsen the situation. Louis left Paris accepting that the French could not help and went to find allies in Low Countries instead.

As order was restored in Languedoc and Flanders was isolated from the rest of the kingdom, Charles formally renewed the Franco-Castilian alliance with the new King Juan of Castile. He sent an embassy to Scotland in an attempt to open a new front in the war against England. Negotiations continued with Brittany, but no real progress had been made even as a six-month truce between the king and duke neared its end. Bertrand du Guesclin, constable of France, was dispatched to Normandy ahead of the anticipated English invasion.

Brittany and Saint-Pol
On 6 December 1379, Waleran III, count of Saint-Pol, surrendered himself to the English. Saint-Pol had been captured near Calais in 1374 and ransomed in September 1378 for the hefty sum of 150,000 francs (£25,000). The count had been released upon receipt of the first third of the ransom, but he was unable to fully raise the second installment, which was due in September 1379. He returned to England for his failure to pay as agreed. Incredibly, he asked for the hand of Maud Holland in marriage and proposed an alliance with the English upon his return.

Maud Holland was the eldest daughter of Thomas Holland and the dowager Queen Joan of Kent. Thomas's death in 1360 and Joan's subsequent remarriage to Edward of Woodstock, the Black Prince, made Maud a stepchild of the heir to the English throne. The Black Prince arranged for her to wed Sir Hugh Courtenay, heir to the earldom of Devon, but Courtenay's death in 1374 left her a widow at just 19. Maud rejoined her mother's household and there she met Saint-Pol, a young noble prisoner of the crown, in the late 1370s. The two fell in love.

French disregard for Saint-Pol's situation, both during his captivity and again as he struggled financially after his release, had turned the count against the Valois. Saint-Pol offered to put all his lands at the disposal of the English, to renounce his homage to Charles V, and to do homage to Edward V as the rightful king of France. In exchange, he would take Maud as his wife and the crown would forgive one-third of his original ransom—i.e., 50,000 francs (£8,333)—in lieu of a cash dowry.

In and of itself, Saint-Pol's proposal had little support. Saint-Pol was a green knight, just 24 years old and having spent most of the past six years as a prisoner. His lands on the Flemish-Picard border were of little strategic value to the English. It was a bad match for the king's stepsister, who could be used to secure an alliance with a more distinguished and experienced figure. Simply put, the English had more use for the count's money than they did his support. Saint-Pol and Maud were resolute, though. Not even the disapproval of the dowager queen would discourage them.

On 20 February, a delegation arrived from the court of Jean IV, duke of Brittany. Five months of peace talks between Brittany and France had gone nowhere and the Bretons had grown disgusted with the refusal of Charles V to give ground on any major issue.

The English gladly welcomed the chance to forge a new alliance with Brittany, especially given Jean's newfound political strength in the duchy. The French attempt to annex the duchy had so repulsed the Breton nobility that the delegation sent to negotiate an alliance with England included longtime supporters of the Blois-Penthièvre faction, which had been directly supported by the French crown for decades.

Talks moved quickly. The English dropped the demands that had held up sealing a treaty with Jean a year earlier, meaning that he did not have to perform homage to Edward V or commit to supporting English efforts outside of Brittany. The Bretons recognized English control of Brest, Saint-Malo and the towns of western Brittany. The two sides committed to defend one another from any attack on their lands in the duchy.

On 1 March, the Anglo-Breton alliance was sealed. The English suddenly took an interest in Saint-Pol's proposal. The French still had control of Nantes, the ducal capital and France's only remaining position in Brittany. England was now committed to its liberation, but the 3,500 men that it had intended for a northern campaign would not be enough to retake the city. The Bretons could only commit 1,000 men to a siege while defending the marches against French invasion, which would still likely still not be enough.

On 30 March, the English sealed an alliance with Saint-Pol. The count committed himself to raising 300 men from his lands and recruiting 500 mercenaries in the Low Countries, at England's expense. Two days later, Saint-Pol and Maud were wed at Windsor Castle. Gloucester's port of embarkation was changed to Sandwich. His army was now to be ferried to Calais and to join with Saint-Pol's forces in Picardy before launching a chevauchée across northern France and laying siege to Nantes. The campaign was delayed a month to allow time for Saint-Pol to act.

Saint-Pol returned to the continent in early May to raise men for the coming campaign, but the French had already learned of the count's betrayal. Enguerrand VII, lord of Coucy, was sent to arrest Saint-Pol and bring him to Paris. Saint-Pol had no time to organize a response and fled at once. He managed to stay one step ahead of Coucy, fleeing from castle to castle and town to town across Picardy into Cambray and then to Hainaut, where the regent of Hainaut arranged for Saint-Pol to return to Calais. Coucy took control of Saint-Pol's lands and installed French garrisons across the region.

On 18 June, ferries began moving Gloucester's army to Calais. The successes of 1379 drove a huge recruitment and the size of the army grew beyond what had been planned. More than 3,700 had gathered by the time of departure. It took two weeks to move the men, horses, equipment and supplies. Gloucester himself arrived on 29 June and the last shipments came in three days later.

Saint-Pol's failures were a serious setback. The army was hundreds of men short of what had been expected and their route into the heart of France had been cut off. The English had intended to make for Cléry, a crossing over the Somme that sat between Saint-Pol's many fortresses in the area, and pillage the rich lands of Champagne before terrorizing the Paris suburbs. Coucy now controlled the bridge. Despite the setbacks, the English had to move. The longer they dallied in Calais, the more French forces would arrive and the more Gloucester's army would be hemmed in.

On 5 July, Gloucester led the English out of Calais. Marching south, he inadvertently trod the trail his father had followed on the Crécy campaign, but in reverse. The duke marveled that the villages before him had been emptied, as people crammed into the principal walled towns of the area. These towns had been built up into major defensive positions after decades of war. As they could not be taken quickly or easily, the duke ordered everything not protected by their walls burned. Homes, farms, and fields were all put to the torch.

The English reached Abbeville on 15 July. They found the bridge over the Somme unguarded. Gloucester ordered his men to cross. The campaign through Artois and Picardy had been easy. It had seemed too easy to the veterans Calveley and Knolles, but to Gloucester it only reinforced his notions of English superiority.

Across the Somme and roughly a half-day's ride from the bridge at Abbeville, Guesclin was encamped with an army of 3,000 men. The countryside had been emptied of food and livestock, its people moved to fortified towns. Every fortress in the area had been garrisoned in preparation for the English arrival.

Gloucester sent a scouting party of five knights forward, but they did not return. Fearing the worst, a forward company of 200 men was formed under the leadership of Sir Thoms Percy. Riding roughly 30 miles ahead of the main army, Percy's company was set upon by the French and forced to retreat after taking heavy casualties. In response, Gloucester tightened his ranks and marched his men in battle formation as they proceeded deeper into Normandy. This offered better protection, but greatly limited the damage they could inflict on the area.

Guesclin pursued the English from a safe distance. Coucy joined him with 500 men from Picardy. The two armies were now roughly the same size, but the French refused to give battle. Instead, they slowly ground the English down. Scouts and stragglers were captured or killed. Any company that broke formation was slaughtered. The English ate through their supplies and there was no food left in the area to steal. They lacked even the ability to forage for fear of French attack.

The English reached the Seine on 27 July, but spent five days trying to find a crossing. Once across, they were dogged by the French all the way to the Breton marches. French captains argued for a full-scale attack to crush the starved and weary English, but Guesclin would not give battle under any circumstance. Gloucester was allowed to slip through French defenses and into Brittany.

Siege of Nantes
On 28 August, Gloucester arrived at Rennes. Jean IV met the English with 600 of his own men, far short of the 1,000 that Breton ambassadors had promised. Gloucester called in reinforcements from English positions at Brest and Saint-Malo, but only a few hundred could be spared.

On 16 September, Charles V died. Three days later, the Anglo-Breton army arrived at Nantes. French forces under the command of Olivier V de Clisson had reinforced the citadel, which was well prepared for a long siege. The two dukes divided their forces three ways. The first division, led by Jean and supported by Knolles, was encamped northwest of the city. William Latimer, 4th baron Latimer, and Calveley took the second division east of the Erde. Gloucester led the final division to the small islands in the Loire south of the city. Their position was weak. They numbered far too few to fully encircle the city and Latimer's division was vulnerable to attack.

Gloucester remained committed to carrying out the siege despite the setbacks. Control of Aquitaine was the ultimate goal of both England and France, but the English had no easy access to the region. It had chronic problems with shipping capacity and Gaunt's disastrous 1373 chevauchée had proven the long overland route across the Massif Central was impossible. Control of Nantes had the potential to transform the situation, allowing English armies to ferry across the Channel to Saint-Malo, cross the Loire at Nantes and move into the open plain of Poitou. From there, all of Aquitaine would be open to them. Gloucester wrote to England for more men.

Secretly though, Jean had begun considering other options. The death of Charles V had radically altered the crown's interest in Brittany. The king had been the architect of the annexation and inflexible in negotiations with the Bretons after the duke's return. Anjou, the new regent of France, had never fully supported the annexation and had been genuinely committed to solving the situation diplomatically both before and after the Breton rebellion.

On 13 October, Anjou opened a diplomatic channel between Paris and Rennes. English captains quickly took note of the diplomatic bustle surrounding the Breton camp outside Nantes, as couriers shuttled to and from Rennes. Gloucester was fobbed off with assurances that it was only part of the normal management of the duchy, as Rennes had acted as de facto capital while Nantes was occupied by the French. An outbreak of dysentery in November gave Jean an excuse to abandon the siege. Feigning sickness, he left Nantes with promises of his return and made for Rennes to more directly manage talks with the French.

Dysentery destroyed the English army. Exhausted and starved, the men's health was already poor before the outbreak, giving the disease a high fatality rate. Ralph Basset, 3rd baron Basset of Drayton, died early on. A Gartner knight and veteran of Poitiers, he was one of the most experienced and respected men under Gloucester's command. As campaign marshal, Basset had kept order as the army starved in Normandy and began a futile siege. That order broke down quickly with his death. A spat between Englishmen and Bretons in the northwestern division ended with the accidental death of a Breton squire. As Jean was still at Rennes, the remaining Bretons withdrew from the siege in protest. Soon after, Calveley declared defeat and led a company of Englishmen to Saint-Malo to find transport home.

On 21 November, Gloucester could no longer delude himself. He had fewer than 2,500 Englishmen left under his command. The English were thousands short of what was needed to take the city. In less than six months, he had lost more than a third of his army to attacks, starvation, disease, and desertion. Possible reinforcements from England were still weeks, maybe even months away. He abandoned the siege and moved to Rennes to confront Jean personally.

The breakup of the English army forced Jean's hand in his dealings with the French. The duke's political standing had softened significantly since September. The threat of annexation had united the Breton nobility behind him, but that threat had died with the king and Jean feared that the Blois-Penthièvre faction would abandon him if he did not negotiate a settlement with France. The English presence had bolstered his position for a time, but the English were looking more pathetic by the day. He needed to resolve matters quickly. Luckily for Jean, Anjou was just as desperate to make peace, as the regency was already sliding into a crisis.

On 30 November, Brittany and France signed the Second Treaty of Guérande. It negated the judgment of the parlement of 1378 and reestablished the terms of the 1365 treaty. The French formally recognized Jean as duke in exchange for his homage to the new King Charles VI of France, allowed the duchy to keep a high level of autonomy, and agreed to surrender Nantes to the Bretons without delay. Jean renounced his alliance with England and promised to reclaim Breton lands under English control—i.e., Brest, Saint-Malo, etc.—or pay a fine of 200,000 francs to the French crown, though he would not be called upon to make war with England outside of Brittany.

Gloucester was astonished. He had advocated English support for Jean for years. He had been among the first to call for a campaign in Brittany in 1378 and his entire military career, short as it was, had been spent fighting for Jean's cause. Jean betrayed Gloucester personally and the English generally, returning to the ducal throne not as an English ally but as a French vassal. Jean offered the badly broken English army just 30,000 francs (£5,000) to leave Brittany peacefully after sealing his treaty with France. Gloucester, resigned to his humiliation, accepted the cash to pay his men then moved on to Saint-Malo.

The complete failure of the chevauchée and the betrayal of Jean IV had a crushing effect on the English war effort. England had sent thousands of men to their deaths and spent upwards of £100,000 on Jean's behalf since 1377, and it was all for nothing. Control of Saint-Malo had been made an expensive redundancy and Jean's marriage to Joan Holland was now a diplomatic failure, just as Isabella of England's marriage to Coucy had been and Maud Holland's marriage to Saint-Pol would soon prove to be. In short, England's strategic aims in northern France had been invalidated. It forced the political establishment to dramatically reevaluate the value of English operations in northern France, especially considering the Anglo-Navarrese victory at Estella.

Anglo-Breton relations were ruined. The Second Treaty of Guérande committed Jean to recovering the lands that England held in Brittany, setting the two former allies on a collision course. The breach was so severe that Gaunt even toyed with the idea of endorsing Jean de Blois, son and heir of Charles de Blois and Jeanne de Penthièvre, as the rightful duke and releasing Blois from his English prison to destabilize Jean IV's rule.

Franco-Breton relations were returned to normalcy. Jean enjoyed good relations with the French dukes who managed the regency government. Better still, both of the major figures of the regency, Anjou and Burgundy, had ambitions that drew their attention away from Brittany. As long as Jean abided by the terms of the new treaty, he had nothing to fear from the French crown during the minority of Charles VI.

In Brittany, the Second Treaty of Guérande was hugely popular and Jean managed to hold the Breton nobility together even without the threat of annexation. Brittany was genuinely united behind a duke for the first time since the death of Duke Jean III. Jean IV's longtime rival, Jeanne de Penthièvre, did not go into self-imposed exile in Paris, as she had after the first treaty, and instead lived out the rest of her days in Brittany. Jean IV even sought her advice on matters of state from time to time.
Last edited:
As I mentioned before, I wanted to reformat updates to make them look more like actual Wikipedia articles now that there's a fair amount of content posted. Over the past few weeks, I've gone back and done that to old updates. Moving forward, links to future updates will be embedded in the articles themselves (and removed later). So, ICYMI, the options for the next update is:

[1] Battle of Estella: A look at the Castilian invasion of Navarre
[2] First government of the uncles: A look at the early regency government of Charles VI

You can vote here.
Jesus christ, what an utter disaster!

Good news is that charles the wise is now dead and charles vi is now king. His squabbling uncles are regents. Now the 2 kingdoms are under regencies, the decisive question is: Which Regency will screw up less?
Anjou @ Gloucester:
The Office Michael Scott GIF - The Office Michael Scott Turntables GIFs
Battle of Estella
Battle of Estella
The Battle of Estella was fought on 2 June 1380 between the kingdom of Castile and León and the allied kingdoms of England and Navarre. Castilian forces led by King Juan of Castile greatly outnumbered the Anglo-Navarrese army, which was supported by a large number of Aragonese, Béarnais, and Gascon mercenaries, and which was led by Archambaud de Grailly, captal de Buch.

The Christian kingdoms of the Iberian peninsula were slowly drawn into the Hundred Years War between the kingdom of England and the kingdom of France over the course of the fourteenth century. Queen Jeanne II of Navarre, who had a strong claim to the French throne, first came to her Pyrenean kingdom in 1329. Navarre sat at the literal crossroads of the kingdom of Aragon, the kingdom of Castile and León, and the duchy of Gascony, which was the crux of the conflict between England and France. Over the 1330s and 40s, Jeanne built diplomatic relations with the Spanish Christian kings and maintained close ties with France. In the 1340s, King Alfonso XI of Castile pursued alliances with both England and France at different times. King Edward III of England granted Castilian and Portuguese merchants trade privileges in the 1350s. Finally, in the 1360s, the First Castilian Civil War fully brought Spain into the Anglo-French conflict.

King Pedro of Castile sought to centralize power in the crown and dominate the Iberian peninsula, as his father, Alfonso XI, had done. Pedro's ambition was perhaps the only characteristic he shared with his father, though. He had neither the strategic mind nor strength of character that had allowed Alfonso to succeed. Pedro launched an ill-planned war with Aragon that dragged on for more than a decade and his violent temper and total disregard for the law led the Castilian nobility to revolt time and time again.

King Pere IV of Aragon fended off a series of Castilian invasions in the 1350s and 60s, but was unable to deliver a decisive blow to end the war. In 1365, Pere convinced Pope Urban V and King Charles V of France to raise the funds necessary to recruit the routier companies in support of Enrique de Trastámara, a bastard half-brother of the excommunicant Pedro. In response, Pedro recruited France's enemies in England and Navarre to his cause.

In 1369, after years of intense struggle, Pedro was deposed and murdered. His fratricidal half-brother was crowned King Enrique II of Castile, but the new king did not return Pere IV's support with land in Murcia, as had been expected. Instead, the new usurper king sought to dominate the other Iberian kingdoms just as Pedro and Alfonso had. Portugal was effectively reduced to a client state and Navarre was compelled to surrender a number of towns along its border with Castile. In the end, only Charles V benefitted from Enrique's rise to power and a powerful Franco-Castilian alliance was forged.

Support for the murdered Pedro ran deep in many areas of Castile. These petristas soon found a figurehead in one of Edward III's sons, John of Gaunt, 1st duke of Lancaster, when Gaunt wed Pedro's eldest daughter and heiress, Constanza. Gaunt assembled an impressive anti-Trastámara alliance that included Navarre, Portugal, and Foix, and had tacit support from Aragon. The alliance was an early display of Gaunt's diplomatic skill, but it collapsed after he led the disastrous Great Chevauchée across France in 1373.

In 1378, England and Navarre forged a new alliance against France and Castile, but its quick discovery led the French able to launch a preemptive strike on Navarre's lands in Normandy. Shortly after, Castile declared its intention to invade Navarre.

Planned 1379 invasion
On 6 January 1379, Enrique II issued orders for the invasion of Navarre. Castilian forces were to assemble at the border town of Logroño in early April. The mustering of medieval armies was slow and Enrique was not expected to arrive until early May, when he would lead the army into Navarre alongside his son and heir, Juan de Trastámara.

King Charles II of Navarre dispatched an embassy to Castille ahead of the invasion. It was a clear stalling tactic, but Enrique agreed to receive the Navarrese delegation at Santo Domingo de la Calzada on 18 April. The diplomatic charade lasted a week before the Navarrese ambassadors were sent home empty-handed. Enrique fell ill shortly after. He lingered near death for weeks and died on 29 May.

Enrique's death was not entirely a surprise, as he had been in poor health for some time. The stress of a lifetime at war, which included the murders of his mother and several of his brothers by Pedro, had aged him far beyond his 46 years. Still, the king's death and the disbandment of the army he had gathered was a very convenient turn of events for Navarre and led to speculation that Enrique had been poisoned by one of the Navarrese ambassadors. The discovery of a plot to poison Charles V around this time only added to the speculation. Enrique's son, now King Juan of Castile, vowed revenge.

Juan moved to take control of the government and treasury immediately after his father's death. He convened the royal council, keeping many of his father's men on to advise him. He was crowned in an elaborate ceremony at the Abbey of Santa María la Real de Las Huelgas on 25 July. Soon after, the cortes assembled at Soria, at which Juan created a political crisis.

Juan's grandfather and uncle, the Kings Alfonso XI and Pedro, had centralized power in the crown at the expense of the nobility. The grievances that had built up under Alfonso boiled over in Pedro's violent reign, giving Juan's father, Enrique II, a natural base of support within the kingdom. This noble support brought some badly needed legitimacy to Enrique's cause. Without it, he was just a bastard rebel at the head of a foreign mercenary army. As king, Enrique lavished the old nobility with privileges, lands, and gifts to keep their support. At the same time, Enrique created a new nobility by showering lordships on the knights and captains of the companies who fought for him in the war against Pedro. In short, Enrique had both encouraged the reclamation of noble power while expanding the size of the nobility, making the lords of Castile overwhelmingly powerful by the time of his death.

At the first meeting of the cortes in the new reign, a list of grievances was read out by the representatives of the ignoble classes. It was a damning indictment of the arrogance and power of the nobility, which it was said they displayed in regular acts of violence—injuring and murdering members of the lower classes, destroying homes, and vineyards, stealing cattle, seizing laborers, kidnapping and ransoming wealthy merchants, and more. Juan, in a demonstration of both genuine concern and extreme political stupidity, declared such violent acts illegal and swore to bring both the perpetrators and those who harbored them to justice. Juan, in his first major act as king, thus alienated the nobility whose support underpinned his own dynasty.

On 14 November, Juan made the long-expected announcement that he would lead an invasion of Navarre, just as his father had intended to do. Juan declared that Navarre would submit to Castile or, should it resist, he would annex Navarre to the crown of Castile. The position Juan took offered no room for compromise. Castilian forces were ordered to begin mustering at Logroño on 1 April 1380.

England and Navarre
In December 1379, the cortes of Navarre assembled in Olite. The kingdom faced nothing short of total extinction. It was dwarfed by the might of Castile. Attempts to negotiate with Juan had been flatly rejected. An embassy to England led by the crown prince had not yet returned and the length of its mission provoked fears that the English would leave Navarre to its fate. Fearing they were on their own, the cortes granted the king 60,000 florins (£8,500) for the defense of the realm, the single largest tax in the kingdom's history.

As the cortes was meeting in Olite, the diplomatic mission to England was finally coming to a successful end. Gaunt, now regent of England, reaffirmed the English alliance with Navarre and, as pretender king of Castile, forged his own alliance with the Navarrese. The English made a £4,000 loan to Navarre and orders were issued for John Neville, 3rd baron Neville and lord lieutenant of Aquitaine, to make 1,500 men available for the defense of Navarre ahead of the anticipated Castilian invasion.

Neville had barely 1,000 men under his command, most of whom were tied up in garrison duty, and so could provide nowhere near the number to which Gaunt had committed him. In early 1380, Neville determined he could spare no more than 400 men for the defense of Navarre. He gave their command to Sir Thomas Trivet, one of his most resourceful and energetic captains, and ordered them to move out once the snow cleared from the passes through the Pyrenees. They were to assist in the defense of the kingdom's principal towns and fortresses until reinforcements could arrive from England.

In England, Gaunt had to manage a loaded agenda. English resources were stretched dangerously thin, with plans for two campaigns on the continent and one in Ireland. The southern continental campaign, aimed at bolstering Neville's position in Gascony and providing for the defense of Navarre, was Gaunt's top priority. The Castilian invasion, expected in the spring even before Juan's declaration, gave the English little time to act. Writs were quickly issued for the mustering of men and requisitioning of ships. The aged Sir Matthew Gournay was appointed to lead the army of 1,500 men to Bayonne in early April.

Charles II desperately dispatched ambassadors to Aragon and Foix. Aragon had spent three decades trying to contain Castile and prevent its domination of the peninsula, but the cautious Pere IV would not come to Navarre's aid. Aragon was not strong enough to defeat Castile on its own and Pere, recalling Gaunt had failed his allies in 1373, did not believe the English would actually follow through on their commitments to defend Navarre. Gaston III, count of Foix, had much to lose if Castile extended its reach into the Pyrenees, but profoundly hated Charles on a personal level. Foix would not aid Navarre directly, but he also would not telegraph England or Navarre's movements to Castile or France.

Trivet crossed the Pyrenees in early spring with 400 men from Gascony. Their arrival in Pamplona buoyed spirits in the city. Charles II managed to raise about 1,500 men from within the kingdom and his bastard nephew Charles de Beaumont recruited about 1,200 more from the mercenary bands of Béarn, Catalonia and Gascony. Gournay's arrival with 1,500 men from England and additional forces led by the Anglo-Gascon lord and longtime ally of Navarre Archambaud de Grailly, captal de Buch, brought the Anglo-Navarrese army to just under 5,000. It was more than the Navarrese had thought possible months earlier.

Grailly was the uncle of the most illustrious captal de Buch, Jean III, who died childless in 1376. His family had been champions for the English cause in Gascony and had long supported the king of Navarre. Grailly himself had fought alongside the Black Prince at Poitiers and for Charles II at Cocherel before inheriting the captalate upon his nephew's death. His experience in battle and his family's esteem made him a natural choice to command of the Anglo-Navarrese army.

Juan remained at Logroño until late May, weeks longer than intended. The king knew his political position was weak, both at home and abroad. He had failed to end noble violence against the lower classes and had not yet received the submission he expected from the king of Portugal, who had recalled several Portuguese galleys from the Castilian fleet. Juan wanted to make a show of overwhelming force against Navarre to bring his own lords into line and to reassert Castilian dominance in Iberia. He thus lingered in the Navarrese marches so as to allow time for men from across the realm to arrive and swell the army's ranks.

The army was large. About 16,000 fighting men had answered the call to arms, with many more there to support the army and manage supply lines. There were more than 3,000 heavy cavalry, nearly 1,000 light cavalry, 5,000-6,000 crossbowmen, and many thousands infantry. It was far more than was necessary to crush the tiny kingdom of Navarre. The famously unmartial Charles II panicked as reports on the Castilian army trickled in, dispatching a last-minute delegation to Logroño. Juan refused to receive the ambassadors.

On 28 May, almost exactly a year after the death of Enrique II, Juan raised his standard and the Castilian army finally moved out of Logroño, spreading out across Navarre. A detachment of about 2,000 men went north to enter Navarre via Vitoria. It was hard terrain—mountainous, sparsely populated and with little arable land—but the road through the region would bring the Castilians north of Pamplona, cutting off the possibility of retreat through the Pyrenees. A larger detachment of about 4,000 men moved southeast along the Ebra, devastating the region before dividing its forces roughly in half. The first division went north, approaching Estella from the southeast, while the second division continued along the Ebra toward Tudela. The king personally led the main army northeast from Logroño, approaching Estella from the southwest. The main army and the first division of the second detachment were to meet at the town and attack it from two sides.

The capture of Estella was a crucial first step in the conquest of Navarre. It was the wealthiest town in the kingdom, providing nearly a quarter of its tax revenue. The lands surrounding it were fertile and the road that ran through it was low-lying and flat, making it by far the easiest way for a large army to approach the capital of Pamplona. Just a short three-day march from Logroño, Estella was also one of the most important towns in Navarre's border defense. It was here that the Anglo-Navarrese planned to make their stand.

The Anglo-Navarrese occupied a hill near Estella, a position chosen by Grailley. It numbered about 4,000, as many of the men gathered for the defense of Navarre had been dispatched to reinforce garrisons at key positions like Tudela and Olite. The army dug ditches and pits in the side of the hill and built barricades with stakes and caltrops to create a highly defensible position.

The Castilians arrived on the morning of 2 June, having taken time to plunder the countryside on their approach. They paused near Estella to discuss a plan of attack, which led to a heated debate that divided the Castilian captains. Juan, just 21 and having never before commanded an army, had retained most of his father's advisors. These older men, many of them veterans of Enrique II's wars, cautioned against giving battle. Younger men filled the king's entourage, though, and they held to an overly idealistic concept of chivalry. Failing to meet the Anglo-Navarrese in battle, they said, would brand them as cowards and dishonor the king. Their young knights' words played to Juan's fears that he was viewed as weak. His campaign was meant to shock and awe his lords and the other Spanish Christian kings. He chose to fight.

Grailly arranged dismounted cavalry and infantry in the center, with crossbowmen and English longbowmen on the flanks. It was a standard English battle formation and the only way for the Anglo-Navarrese to counter the Castilian army's huge numerical advantage, as Juan had about 10,000 men under his command.

The battle began around midday. The Castilians opened hostilities by launching a heavy cavalry charge, hoping to break the order of the Anglo-Navarrese line and end the battle quickly. They failed. The slope of the hill and the rows of ditches and pits slowed the Castilian cavalry. Momentum was the cavalry's greatest advantage and, having lost that, the mounted knights became easy targets for the archers. The Castilians suffered heavy losses from the start. Those cavalrymen who survived made little to no impact once they reached the Anglo-Navarrese line, being knocked or pulled from their horses and sent to the rear as prisoners.

As the cavalry disaster unfolded, the Castilians ordered the main body of their infantry forward. It vastly outnumbered the Anglo-Navarrese, but it too struggled on uneven footing. The Castilian line became badly disorganized as it stumbled uphill under heavy arrow fire and its men were exhausted by the time they hit the well-ordered Anglo-Navarrese defensive line.

Intense fighting ensued. Scores of Castilians were crushed under the weight of their own men, falling to the ground and being trampled to death as the mass of attackers continued to climb uphill. The Anglo-Navarrese could not withstand the onslaught forever and were slowly pushed back. Seeing the line begin to buckle, Grailley withdrew the ranged units and ordered the Anglo-Navarrese rear guard forward. Both sides began taking heavy casualties.

After only a few hours of fighting, the Castilian king's banner fell near the front line. Men in the Castilian rear watched for it to be raised again, but the front line was too tightly packed for anyone to reach it. Believing the king was dead, the rear of the army began to flee the battlefield. Their flight spread panic through the ranks and the Castilans broke into a chaotic retreat.

As the retreat had begun from the rear, it took time for those at the front to realize what was happening. A body of Castilian knights formed around Juan and began to cut down their own common soldiers to get the king through the mayhem and to safety. The Anglo-Navarrese line surged forward, chasing their enemies down the hill. Grailley ordered his knights to take to their horses and ride down the retreating enemy.

The bloodshed continued through the late afternoon. Castilian losses are estimated at more than 2,000, while the Anglo-Navarrese lost only about 500. Any man of value who could be caught was taken prisoner, of which there were many. The retreat from the rear meant that it took time for those Castilian nobles fighting dismounted along the front line to realize that the army was melting away behind them, leading many to be captured before they could reach their horses. The list of prisoners was long and the ransoming of noble prisoners took time, depriving Castile of experienced cavalrymen for years to come. Over this time, hundreds of thousands of doblas flowed to Englishmen, Gascons, Navarrese, and others who had taken prisoners at Estella.

King Juan, however, was not among the captured or the dead. The king and his bodyguards had managed to escape the chaos. They made a hurried retreat back to Logroño, but stayed only briefly before fleeing further west toward Burgos.

It would take days for news of the disaster at Estella to reach the detachments of the Castilan army. The first to learn of the battle was the division that had moved along the Ebra and then turned north toward Estella. Its men arrived at the town only a day after the battle. They were outnumbered two-to-one by the Anglo-Navarrese army, leading to their quick defeat and the capture of yet more prisoners. The second division of the Ebra detachment met resistance at Tudela, but quickly retreated back to Logroño as word of the battle spread. The detachment sent north through Vitoria reached Pamplona days later. Roger-Bernard IV, viscount of Castelbon, led the city garrison out of the gates to chase the Castilians back down the desolate road they'd come.

Grailly had achieved an enormous and unexpected victory. It was a decisive blow against Castile that brought the captal fame and glory. Castelbon acted quickly to forge an alliance with the newly-renowned captal, arranging a marriage between Graily and Isabella de Foix-Castelbon, the viscount's only daughter.

Both Castile and the house of Trastámara were badly shaken by the Battle of Estella. The other Iberian kingdoms quickly took advantage of the situation. Over the next year, Charles II retook control of Logroño and Vitoria, Pere IV pushed Castile to cede territory in Murcia, and King Fernando of Portugal prepared for war. Juan's position was further weakened by the death of his chief ally, Charles V, later in the year. The new King Charles VI of France was a child and the French regency government was dominated by a pair of royal uncles whose personal ambitions drew much of their attention away from the struggles of Castile.

As Castile's position in western Europe shrank, so too did Juan's position within his own kingdom. The older members of the king's council who had advised against the attack became embittered towards the younger men who had goaded Juan into giving battle. Those who supported the attack burned with anger. They declared those who began the retreat to be traitors and wanted nothing more than to avenge the loss, pushing for an even more aggressive policy against Navarre and the increasingly antagonistic Portugal. Juan, a fragile young man, blamed himself for the disaster and isolated himself from others. He fasted for days and begged for forgiveness and guidance in prayer. Factions began to emerge in the king's absence, which Juan would struggle to bring together once he returned to court.

These things helped to revive interest in John of Gaunt's rival claim to the throne. Gaunt had done little to advance his cause since the mid 1370s. The last major petrista uprising came in 1374, when Gaunt had been expected to invade the country at the head of a major army. The failure of the Great Chevauchée, which was followed by the collapse of Gaunt's Iberian alliance, left his supporters in Castile dangerously exposed and Enrique II responded by executing the would-be rebels. The English government had neither the interest nor the resources to support Gaunt in another Iberian venture in the years that followed. At one point, Gaunt even tried to negotiate the surrender of his claim, but Enrique would not consider it. Now, Enrique's son would pay for such hubris. The Anglo-Navarrese victory at Estella and the failure of Gloucester's chevauchée, which was a major setback for the English in northern France, turned English attention south. The parliament of 1380 would be dominated by debate over how and when to send Gaunt to Castile.
Last edited:
ICYMI, there are three options for the next update:
  • Third Fernandine War: Portugal finally declares itself for England and John of Gaunt
  • First government of the uncles: Charles V's well-laid plans for a regency are tossed out
  • Parliament of 1380: England tries to find a path forward after Gloucester's failure and Brittany's betrayal
Click here to vote.