by L. J. Andrew Villalon  
                                                                            Associate Professor of History  
                                                                            University of Cincinnati  

In March, 1351, sixty warriors walked onto a field in the Duchy of Brittany; and, at a signal, began to fight. (1)   Half of them, French knights besieging a town, took on an equal number of English defenders, in an encounter lasting for several hours which became known as the Combat of the Thirty.  The French triumphed when one particularly rash Frenchman mounted and charged his horse into the English ranks. (2)   While no more than a minor incident in a sideshow of the Hundred Years War, the Combat was one of those beaux gestes which fired medieval imaginations and brought honor to all involved.  Among the Englishmen said to be present (3) were two young warriors destined to rank with the famous captains of the age or, as one historian has called them, England's "dogs of war (4)"--Sir Robert Knolles and, the subject of this study, Sir Hugh Calveley. (5) 

After a brief overview of Calveley's career, this article will explore in detail his role in a little known chapter of the Hundred Years War, involving the intervention of France, England, and the so-called "free companies" into Iberian warfare.  The conclusion will look at the results of that intervention and their significance for Calveley. 


Disappointingly few references exist from which to discover much about Calveley's background or early years.  The first source to shed real light dates to 1354, at which time he was operating in Brittany, commanding his own company in the army of John of Montfort, the English-backed claimant to the duchy. (6) For their services, he and his men earned in addition to their pay a blanket pardon from the crown for "all manner of felonies and trespasses," an important fourteenth century incentive for "taking the king's shilling." (7)  The documents do not yet refer to Calveley as "knight" or "chivaler"; and in fact, other sources suggest that he became Sir Hugh only around 1361. (8) 

From the mid-1360s through the early-1390s, Calveley's movements are fairly easy to trace, due in part to the interest he aroused in such chroniclers as Froissart (9), Walsingham  (10), and Ayala (11) , and in part to his appearance in scores of documents from the English Rolls Series.  Even after his departure from the battlefield, and therefore, from the chronicles, he turns up in the Rolls Series often enough to provide some idea of what happened to him during his waning years. 

As a result of their victories at Crecy (1346) and Poitiers (1356) and their capture of Calais, the English took the opening round in the Hundred Years War, a decision clearly reflected in the harsh terms which the Treaty of Bretigny (1360) imposed upon the French. Although officially at peace after signing the treaty, the two kingdoms continued their struggle indirectly, by participating on opposite sides in several lesser conflicts, including the civil war in Brittany and the War of the Two Pedro's (1356-1366) in Spain.  In both of these secondary conflicts, Sir Hugh Calveley would play a significant role. 

Through the mid-1360s, he continued to serve primarily in Brittany, where he built up a formidible reputation, in particular by his conduct during the decisive battle for the duchy. (12)   In September, 1364, on the field of Auray, Montfort's army under the overall command of Sir John Chandos, took on a Franco-Breton force supporting the rival claimant, Charles of Blois.  Calveley, much to his own disgust, was assigned to command the reserves.  His skillful handling of this force, however, contributed enormously to Chandos’s victory over the French, who were led by their future constable, Beltran duGuesclin. Charles of Blois's death at Auray cemented Montfort's hold on the duchy.  What is more, numerous French knights were taken prisoner, including DuGuesclin himself (the first of several times this colorful figure would fall into enemy hands). (13) 

Ironically, the victory, by ending the Breton war, threw Calveley, like a many another soldier of the period, temporarily out-of-work.  This led to an odd, but extremely significant chapter in the English knight's career, during which he became deeply involved in affairs south of the Pyrenees.  Here, by a strange twist of fate, Calveley, fighting as a member of the free companies, managed to serve all sides in a complicated war which pitted Castile against Aragon and ended in a civil war for the Castilian crown (see below).  This "Mediterranean interlude" ended abruptly in 1369 when open warfare once again broke out between France and England, and Sir Hugh returned north to take up arms for his sovereign. 

Ironically, Calveley's military career reached its peak in the 1370s, at a time when his country suffered a series of disasters.  It was during this decade that France, under the leadership of Charles V (1364-1380) and his indominable constable, drove the English from most of their hard-won gains on the continent.  With some guidance from his sovereign (appropriately nicknamed Charles the Wise), DuGuesclin had learned the lessons of earlier mistakes and designed a strategy which exploited both French strengths and English weaknesses.  Avoiding set-piece battles which had became the grave of French chivalry, he chose instead to chip away at the English position, besieging towns, overwelming small groups, fomenting rebellion among England's French subjects--in short, conducting the kind of "guerrilla" war which minimized the battlefield advantage of the English longbow while maximizing the French advantage in numbers.  Meanwhile, England's greatest general, Edward, Prince of Wales (1330-1376) (better known as the Black Prince) was effectively neutralized by the lingering disease that forced him to relinquish command in 1371, and killed him five years later. 

Caught in these changing times, English captains like Calveley now found themselves on the defensive, shunted from one trouble spot to another.  Following his return to the army in 1369, Sir Hugh first operated in Gascony, ravishing the lands of nobles who had deserted to the French. (14).  Later, he moved north joining an invasion of Anjou, where he established himself along the Loire and terrorized surrounding French territory. (15)   In 1373, he signed onto what would prove to be the final campaign led by King Edward III (1327-1377). (16)   The following year, he accompanied the Duke of Lancaster on a grand cavalcade through northern France--which accomplished little when it failed to provoke the French into a general engagement. (17)

From 1375 to 1378, Calveley served as military governor of Calais, England's major entry point onto the continent, after which, he became Keeper of the Channel Islands with life tenure.  From both, he kept up pressure on the French. (18)   For example, in 1377, he descended on Boulogne, capturing or burning more than twenty ships and most of the port.  In the lurid glow of spreading fires, he ordered his nervous chaplain to perform a solemn mass, after which he consigned the town to a bloody plunder--a darkly humorous and faintly blasphemous episode, not uncharacteristic of the man. (19)

Calveley's final years of campaigning in France again centered on Brittany, where he helped to defend John of Montfort's sometimes tenuous hold on the duchy.  Service as England's Admiral of the West had him conveying British troops across the channel to Brittany and taking part in several sea battles. (20)  In 1379, his fleet was shipwrecked off the Cornish coast, with considerable loss of life.  On this occasion, Sir Hugh and seven companions survived by desperately clinging to the rigging of a wreck until it washed ashore.  When he made his way back to London, he found himself being mourned among the dead. (21)

In 1380, England mounted a large expedition to the continent under the youngest of the royal uncles, the Earl of Buckingham.  Calveley accompanied the earl who took a wide detour through northern France, swinging as far west as the County of Champagne, pillaging and burning.  Although Calveley had no trouble finding action, once again, the attempt to force the French into a general engagement met with frustration. (22)

When Buckingham's army finally arrived in Brittany, they received an ugly surprise.  Montfort's ardor for their presence had cooled when he discovered that his subjects, while ready to accept his rule, were still unwilling to support his English backers.  To make matters worse, the succession of a new French king, Charles VI (1380-1422), had greatly increased the chances of a lasting peace between France and Brittany. Consequently, while continuing to speak soothing words to the English, Montfort broke one commitment after another.  When  he solemnly promised to do better the following year, the English, including Calveley, spent an uncomfortable winter in Brittany, only to find with the coming of spring that their ally had been conducting secret negotiations with the French, ending in an accord. (23)

The year 1380 witnessed the death of the two men responsible for reversing the course of the Hundred Years War--first, Constable DuGuesclin; and, a few months later, Charles V.  With their disappearance, the conflict settled into a stalemate, one that left the French firmly in control of most of their own kingdom.  The military situation, accompanied by Calveley's advancing age, led to the winding down of his career.  Sources show him involved in just two more adventures.  In 1383, he took part in a notorious episode, known as the Norwich Crusade, preached by the Roman pope against his rival at Avignon. (24)    It quickly degenerated into a philibustering expedition through Flanders, and ended with an inglorious failure for the English.  Calveley's military swan song occurred three years later when he accompanied his longtime patron, the Duke of Lancaster, back into Spain, in a futile attempt to secure the Castilian throne. (25)

Although Calveley's retirement from the battlefield led to his disappearance from the chronicles, he continues to show up with some frequency in Rolls Series documents, indicating that as he abandonned the life of the camps, he adopted the peaceful pursuits of a fourteenth century English gentlemen.  He served as justice of the peace for Berks County, and twice represented Rutland in Parliament. (26)

Ironically, one of his final public acts came in July, 1388, when he joined the English Peace Commissioners negotiating a truce with France, one which began a long hiatus in the Hundred Years War. (27)   The conflict would not heat up again until 1415 when Henry V reasserted the ancient Plantagenet claim and won another stunning victory at Agincourt--by which time Hugh Calveley had disappeared from the scene.  He died without issue in 1393, at over sixty years of age. (28)


The Hundred Years War, for all its devastation, was by no means a continuous struggle.  There were long periods when little or no fighting occurred. One of the most important of these began after the signing of the treaties of Bretigny and Calais in 1360 and endured for the better part of a decade.  It was then that France experienced a serious threat from roving bands of soldiery, discharged by both sides for reasons of economy and then left to fend for themselves.  These hard-bitten veterans, sometimes numbering in the thousands, banded together into 'free companies,' living off the land and its civilian population, while awaiting the renewal of open warfare, which would lead to their recall. (29)

An apparent pre-condition for this scourge was a system of warfare in which individuals like Hugh Calveley recruited companies of fighting men and then sold their services to one or another of the combattants. (30)  It is not surprising that when hostilities wound down and they were thrown out of work, such men, “long accustomed to pillage (31)" and used to functioning in “private” companies, would simply convert themselves into bands of brigands, living off the country. 

In 1360-61, following the return of the debonair, but ineffectual French king, Jean II (1350-1364), from his first captivity in England, both sides began to implement the recently-signed treaties.  As a result, garrisons were called upon to surrender towns and castles they had held and to disband.  While some complied, many others did not.  If leaders left their companies, the men elected replacements.  Their burgeoning numbers, which by Lent, 1361, are said to have exceeded 16,000, included French- and Englishmen, Gascons and Bretons, as well as a smattering of mercenaries recruited from other lands. (32)  The companies threatened the major French city of Lyon and bragged that they would "pay a visit" to the pope and cardinals at Avignon.  For those regions of France which experienced their depredations, in particular Champagne, Burgundy, and Languedoc, peace and war became indistinguishable. 

Several chronicles note that throughout this period, French territory suffered the most serious damage.  By contrast, the English-held duchy of Aquitaine escaped relatively unscathed, leading many in the French camp to accuse England of violating the peace by acquiescing in, if not actually directing, the war-like activities of the free companies, many of whose captains were either English or Gascon.  Such groups formed a ready reserve of fighting men that England did not have to support, but which she could tap for military service at a moment's notice.  Consequently, royal orders to cease and desist preying on "our very dear and much-beloved brother, the king of France," such as the one Edward III addressed to Hugh Calveley in 1364, may have been more for show than anything  else. (33)   Froissart’s aptly summed up the situation with these words: “the wisest of the kingdom declared that if something were not speedily done, either by fighting or getting them out of the country, they would destroy the noble kingdom of France!" (34)

Unfortunately, the French monarchy, badly weakened since the defeat at Poitiers, proved unable to cope with the companies.  Soon after returning from England, King Jean received from the royal council a dire warning that 

    unless these bands were repressed, they would multiply so much and do so much mischief, to judge from what they had already done, that the kingdom of France would suffer equally as during the war with the English. (35)
Acting on the council's advice, the king commissioned his cousin, James de Bourbon, Count de la Marche, to raise an army with which to crush the companies.  However, when the two sides met at Brignais around Easter, it was the royal army rather than the companies which experienced a humiliating defeat, suffering losses which included Bourbon and his son. (36)    After Brignais, some of the companies drifted off to fight in Italy (37); the rest, however, continued their activities, in which they met little resistance from a population cowed by Bourbon's defeat.  When a crusade preached against them by Innocent VI  failed to materialize, the papacy was reduced to buying off their threatened attack on Avignon. (38)

In 1364, Montfort's victory in Brittany increased the already considerable danger posed by the free companies.  Followed almost immediately by the end of a small war between France and Navarre, it led to the release of large contingents of fighting men, who, in their unemployed state, now swelled the companies’ ranks. (39)   Among the most notable recruits to join at this time was Hugh Calveley. 

In the same year (1364), Jean II died in England, having voluntarily returned to captivity.  As a result, the crown passed to his son, Charles the Wise, who together with the new pope, Urban V (1362-1370) (40) began casting about for a means of removing the companies from French territory.  One attractive solution--to ship them off to southeastern Europe to fight the Turks--foundered on the companies' refusal to journey so far from home.  Charles and Urban then decided that an even better solution lay closer at hand:  just across the Pyrenees ruled a figure whom both men detested. (41)


Pedro I (1350-1366/69), better known to history as Pedro the Cruel, had inherited the throne of Castile in 1350 from his father, Alfonso XI, Europe's highest ranking victim of the Black Death.  There followed a turbulent reign of nineteen years during which Pedro earned his unflattering sobriquet.  His increasingly murderous purge of all opponents, real and imagined, and his defiance of the Church alienated large sectors of the aristocracy and the clergy.  Among those whom he eliminated or drove into opposition were his half-siblings, sons of Alfonso by a royal mistress.  By 1360, internal opposition to Pedro's rule had come to center around the eldest of these royal bastards, Enrique, Count of Trastámara, who, in 1363, launched his bid for the crown. (42)   He did so in the full knowledge that he could count on powerful support from outside Castile. 

Despite discontent among his own subjects, Pedro would probably have retained the crown had it not been for the complete failure of his foreign policy.  He soon abandoned the key tenets that had guided Alsonso's diplomatic efforts:  peace with Castile's Christian neighbors, a reinvigorated crusading effort against Moorish Granada, and a moderately pro-French stance in the Hundred Years War.   By contrast, Pedro allied himself with the Moors, launched a major war of conquest (the War of the Two Pedros) against his eastern neighbor, Aragon, and began moving ever closer to England.  The resulting hostility on the part of Aragon, France, and the Papacy eventually led to the foreign intervention which occasioned Pedro’s downfall. (43)

It was apparent to all that a victory over Pedro depended entirely upon redressing the military balance in Spain where, for a decade, Castile had enjoyed an almost unbroken string of successes in its war against Aragon.  The best hope lay in securing the services of the free companies, thus bringing them into the war on the side of Enrique and beleaguered Aragonese.  For France and the papacy, such a had the added-attraction of removing many of the free companies from southern France. 

By autumn, 1365, members of the alliance had reached agreement among themselves that each would contribute part of the price for the companies' services. (44)    Christmas found some 10,000 or more of these men (45) gathering around the city of Barcelona where the Aragonese king, Pere III “the Ceremonious” (1335-1387), welcomed them warmly. (46)

To obtain Du Guesclin's services for the expedition, France had arranged for his ransom. (47)  However, since so many of the companies were English or Gascon, an attempt was made to recruit a high-ranking Englishman to share command.  John Chandos, fully employed as grand seneschal of Aquitaine, declined the offer.  On the other hand, several out-of-work English captains did sign on--the most prominent among them being Hugh Calveley. (48)   Chroniclers leave little doubt that Calveley was the acknowledged leader of the English contingent.  Just as DuGuesclin had been promised the town of Molina and the County of Trastámara for his help, Sir Hugh was slated to receive Carrion also with the title of count. (49)

In January, 1366, the free companies, joined by Enrique of Trastámara and his Castilian supporters as well as a large force of Aragonese 'volunteers' under the Count of Denia, marched westward toward the Castilian frontier.  First contact with the enemy was assigned to Calveley who moved against Castilian forces occupying Aragonese territory. (50)    When these retreated with little resistance, Enrique and DuGuesclin brought up the main body of the army and began the push to Burgos.  Du Guesclin, Calveley, and the Aragonese commander all urged Enrique to declare himself king, a step he took as soon as he entered Castilian territory at Calahorra. (51)

Meanwhile, Pedro, unaccustomed to fighting on the defensive, was making decisions which would  have a disastrous impact on his campaign.  Very early, he passed up an opportunity to "buy off" many of the free companies which owed their primary allegiance to his English ally. (52)   Then, in spring, 1366, with the full force of the companies moving against him, Pedro made an even more fateful choice:  he decided to evacuate Burgos at the enemy's first approach.  Almost alone, he fled southward toward Seville, triggering a mass defection among his followers. (53)   Within weeks, much of the kingdom had gone over to Enrique who now led his mercenaries on a triumphal march southward in pursuit of his rival.  Crowds of Castilians hastened to join the winner.  When even Pedro's beloved city of Seville deserted him, he hurriedly crossed the border into neighboring Portugal. (54)

After taking Seville, Enrique decided to dismiss the majority of the free companies, which were costing him dear, while wreaking havoc on territory that now acknowledged his rule.   Despite the strain on his treasury, he dealt with them generously, after which he sped them on their way out of Castile.  The new king retained only the services of the Bretons under Du Guesclin and the Anglo-Gascon followers of Calveley. (55)   Sir Hugh would remain in Enrique’s service until early spring, 1367, when a radically altered situation forced a complete reversal on his part. 


Calveley's about-face resulted from a shift in English policy toward the crisis.  In 1366, the English had chosen to watch from the sidelines, even though they should have realized that any victory for Enrique would bode ill for Anglo-Castilian relations.  During the 1360s, Pedro had been moving ever closer to England.  By contrast, Enrique would owe his throne largely to French support and could therefore be expected to resurrect the old Franco-Castilian alliance. 

When Pedro reentered Castile in the north after traversing Portugal (56), he dispatched messengers to seek military aid from the Black Prince who governed England's lands on the continent.  Despite some disagreement from his own advisers, Edward decided to respond positively to the appeal. (57)  Perhaps his failure to foresee the crisis or attempt to forestall it had left him believing that he now had little choice but to intervene.  Besides, it had been a decade since his brilliant victory at Poitiers; and a Spanish campaign would give this consummate warrior a chance to get back into the field. (58)

Having called up his vassals and stockpiled supplies, the prince sent heralds to summon the free companies which owed him their allegiance. (59)   Some of the English "companions" had returned to France, others were still operating south of the Pyrenees.  As the call to arms spread, men on both sides of the mountains rallied to the prince's standard, despite French and Aragonese attempts to cut them off. (60)

English heralds even ventured into the heart of Castile, to recall Calveley and his men.  Despite their recent service to Enrique, they owed their primary allegiance to the Black Prince.  Sir Hugh faced a difficult decision for he had found fortune and a noble title with his new employer.  Nevertheless, he and most of the English mercenaries took their leave, marching eastward toward Navarre. (61)   They did not escape unscathed.  For while Enrique may have been sympathetic to Sir Hugh's dilemma, other Castilians along the route were less inclined to observe chivalric niceties.  The English ultimately fought their way out of Castile, ending up in the neighboring kingdom of Navarre where they could await the prince's coming. (62)   Here, they had their major influence upon the campaign. 

For success in his enterprise, the Black Prince had to secure the cooperation of one of the most unreliable figures of the age—Charles II (1349-1387), King of Navarre, appropriately known as Charles the Bad.  To get to Castile, the English would have to cross the Pyrenees at Roncevaux and traverse Navarrese territory.  As usual, Charles (always keen to maximize his profit) chose to engage in a torturous double game, promising first one side and then the other that he would help them. (63)

In the course of this diplomatic waffling, Caveley's men marched into Navarre, where they immediately went on a rampage.  When Charles complained to the Black Prince, the latter merely reminded him that he had not lived up to commitments reached in the course of their dealings.  The implication was clear:  if Charles wanted the prince to call off his captain, then Charles had better mend his ways.  Whether or not Calveley's plundering had been undertaken at the prince's behest, it undoubtedly served his strategic purposes--a salutary reminder for the untrustworthy monarch of Navarre.  Shortly thereafter, Charles once again met the prince's envoys and reaffirmed his promises to allow the English free passage, a commitment which he now kept. (64)

Already south of the mountains, Sir Hugh and his men were spared the difficult winter crossing experience by most of the English army, which they joined only when it reached the city of Pamplona, capital of Navarre.  After a few days rest, the Black Prince swung westward along the Rio Araquil toward the Basque city of Vitoria, where he established a new camp. Meanwhile, the Castilian army, led by Enrique, approached Vitoria from the south, setting up their camp on the high sierra overlooking the town.  Learning of the enemy's arrival, the Black Prince, who hoped for a speedy engagement, drew up his own men and challenged the Castilians to come down and fight. (65)

Still heeding the advice of his French captains who urged him to adopt a strategy of delay, Enrique was not yet ready to exchange a commanding position for the wager of battle. (66)   He therefore declined Edward’s offer.  On the other hand, he was, however, fully prepared to engage in hit-and-run tactics.  A Castilian raiding party led by one of the king's two surviving brothers, Don Tello, quietly slipped off the sierra and proceeded to attack English foraging parties and exposed units of the vanguard.  Among those caught unaware was Calverley, whose position a league in advance of the main army was overrun just as his troops were getting ready for breakfast.  While some of the men were slaughtered in their tents and much of the baggage was lost, survivors, including Sir Hugh, fled. (67)   The panic which gripped the English vanguard was arrested only when the Duke of Lancaster, awakened by the noise, hurried to a nearby hill and raised his standard to provide a rallying point.  Meanwhile, the prince and Chandos hurriedly advanced, forcing the now outnumbered Castilians to withdraw. (68)

While Enrique remained in his unassailable position overlooking Victoria, the situation of the English rapidly deteriorated.  A cold, wind-driven rain fell on the English camp.  Provisions ran short.  In constant skirmishing, the Spanish light cavalry showed to its best advantage, sorely pressing the heavier English knights.(69)   Finally, Edward had had enough.  In the best strategic move of the campaign, he broke camp, retreated into Navarre, and swinging southward, crossed back into Castile at Logroño.  Not only did this move allow the prince to cross the Ebro unopposed; it also placed him on terrain which did not inordinately favor either side.  Here, he could force Enrique either to fight or let him pass unmolested. (70)

Although taken by surprise, Enrique and DuGuesclin recovered quickly.  Operating along interior lines, they were able to recross the Ebro, make a forced-march southward, and arrive at the town of Nájera, twenty-nine kilometers west of Logroño.  Here, they established their camp west of the Najerilla, a small, but swifty-flowing river which cut across the main road.  While lacking the tactical advantage enjoyed in the mountains around Victoria, they still held a river line that Edward would have to force. (71)

Despite French warnings against a general engagement, Enrique was now determined to fight.  While publicly expressing confidence in the ability and steadfastness of his army, he quietly voiced fears that any failure to face the English might trigger a second mass defection--this time away from his side.(72)  Again, acting against French advice, Enrique now made the most serious tactical error of the campaign.  Rather than maintain his position west of the Najerilla, where the river bolstered his defences, he decided to cross over and fight on the large plain to the east.  The decision helped doom Enrique's army to one of the worst defeats of the century. (73)

As dawn broke, on April 3, 1367, the two armies faced each other across a field some kilometers from either Nájera or Navarette - a fact which makes either name for the battle something of a misnomer.  In the center of the Castilian formation, Enrique had placed his most reliable troops, the Franco-Breton mercenaries, many of them veterans of the 1366 expedition.  Here, they were accompanied by the Aragonese and a contingent of Castilians, all under the command of Du Guesclin.  The wings of Enrique's army were composed primarily of Castilian light cavalry and a large, but poorly armed levy of foot, with the left entrusted to his brother, Don Tello, while he himself assumed command on the right. (74)

At a signal, the English vanguard, led by Chandos and the Duke of Lancaster, set in motion toward the strong center of the Castilian line.  Here, the hardest fighting of the day would develop as the two sides locked in hand-to-hand combat. (75)    Meanwhile, the right wing of the prince's main division struck at Henry's left.  As on earlier occasions, Henry's younger sibling, Don Tello, demonstrated his utter unreliability, fleeing from the battlefield even before the two sides could come together—and taking with him most of the left wing.  This allowed the English right to wheel inward and attack du Guesclin's flank while the rest of the prince's division joined into the attack on the Frenchman's front. (76)

During the battle, the Anglo-Gascon free companies were mingled throughout the English army.  Many of these men served in the vanguard under Chandos and the duke, scene of the hardest fighting.  Others, including Calveley fought with the rear guard, over which Sir Hugh shared command.  When the battle began, these troops occupied some high ground on the English left, where they faced the main body of Spanish light cavalry and a huge contingent of foot, commanded by Enrique. (77)

Here, the technological realities of fourteenth century warfare descended upon the battlefield.  Enrique's army lacked the masses of crossbowmen who had accompanied the French in their great battles against the English; and most of those who were present had been assigned to the center.  Consequently, on this end of the line, the Spanish had slings and javelins with which to confront the English longbow. (78)  It was an unequal contest.  In the words of one chronicler who was present at the battle "archers shot thicker than rain falls in winter." (79)   The Spanish light cavalry and foot soldiers, both far less heavily armored than French knights and with little experience of the longbow, faced this withering fire.  Three times Enrique managed to rally them for another attack; three times they were driven back.  Finally they broke and fled, permitting Calveley's division to wheel inward and fall on DuGuesclin's other flank. (80)

Although the battle-hardened Franco-Bretons who anchored the Castilian center continued to fight as long as they could, stripped of support on both flanks, their collapse became inevitable.  In the midst of the carnage, 
many high-born prisoners were taken, including, once again, du Guesclin. (81)

The withdrawal of both wings soon turned into a rout which in turn became a massacre.  With the English in close pursuit, the narrow bridge across the Najerilla, that would have aided Henry had he remained west of the river, now became a deathtrap for his fleeing army.  Hundreds fell into the water and drowned.  Many who actually made it across the bridge were later taken in the town, cowering in houses and cellars. (82)

For Pedro and the English, the only shadow on the day was their failure to capture Enrique.  As soon as they discovered that he had made good his escape into Aragon, they took steps to isolate him.  Edward dispatched as his envoy to the Aragonese Hugh Calveley, who, as a result of the events of 1366, was well-known and well-respected there.  Calveley's mission achieved the desired goal.  Fearing Edward's wrath  and angered by Enrique's failure to turn over border lands promised to Aragon, Pere III readily renounced the fugitive's cause. (83)

Incredibly, back in Castile, Pedro the Cruel now managed to seize defeat from the jaws of victory by alienating his English allies.  To begin with, he murdered several of the Castilian captives, for which unchivalrous and unprofitable conduct he earned the prince's rebuke. (84)   The rift between allies widened considerably when the newly-restored king baulked at paying his war debts.  While recruiting for the expedition, Pedro had not hesitated to make extravagant promises to all who would support him.  Now, he began to hedge. (85)   After much hard bargaining, the pair reached an agreement:  Pedro would go south to raise money in order to pay Edward some mutually acceptable sum yet to be negotiated. 

This was the last Edward would ever see of his ally.  The date for payment came and went with the English army still quartered in northern Castile, suffering through the hot   summer. Messengers to Seville returned loaded only with excuses.  Finally, the prince decided he had had enough.   Having witnessed Pedro's battlefield brutality and waited in vain for the promised payment, he set off for home, all the while complaining bitterly of Spanish perfidy. (86)

As a result of their estrangement, the battle of Nájera, although one of the greatest victories of the fourteenth century, brought little comfort to either of the victors.  Pedro gained only a two year reprieve in his unsuccessful bid to retain the Castilian throne.  In autumn, 1367, as the Black Prince was evacuating the peninsula, Enrique of Trastámara returned, his shattered army rebuilt with French assistance.  Over the next eighteen months, Enrique aided by DuGuesclin (who had once again been ransomed from the English) regained most of the ground lost after Nájera.  Finally, in March, 1369, the pair met and defeated Pedro's main army near the castle of Montiel, south of Toledo.  A few days later, Pedro the Cruel's reign came to an abrupt end when, within hours of being captured, he was killed--his half-brother and successor having wielded the fatal dagger. 

The prestige which the Black Prince gained from his victory at Nájera in no way compensated England for what the Spanish campaign would ultimately cost. To begin with, it may have cost the English their finest general.  There is some indication that during his time in Spain, Edward contracted the disease which would first debilitate and later kill him. (87)  The sources leave no doubt that what started as a glorious adventure ultimately turned into an expensive fiasco.  The prince, who had helped underwrite the expedition, found himself saddled with Pedro's unpaid debts. (88)   When he tried to recoup by imposing an unpopular hearth tax throughout his continental lands, the Gascons rebelled, the French intervened, and the Hundred Years War was back in full swing. (89)   There followed the years of French victory that reversed the judgment of Crecy and Poitiers. 

And what of Sir Hugh Calveley?  Following his successful mission to Aragon in spring, 1367, the English knight disappears from the chronicles for nearly two years.  It is possible that during that summer, he reentered Castile--just in time to march out with the army the following autumn.  Or he may simply have sent word to Edward concerning the outcome of his mission, while he himself remained in Aragon, watching over the estates he had acquired as payment for his role in the 1366 expedition which had expelled Pedro the Cruel from Aragonese territory. 

Either way, documents recently uncovered in the archives of Aragon indicate that when the Black Prince evacuated the Iberian Peninsula in autumn, 1367, Calveley did not accompany him across the Pyrenees.  Instead, Sir Hugh almost certainly remained in Aragon, where he made a serious effort to establishment himself permanently. (90)   In June, 1368, he married Costanza, the daughter of a Sicilian baron and herself a lady-in-waiting to the queen.  From this marriage, Calveley acquired a substantial dowry, augmenting his already significant holdings in the eastern kingdom. (91)   In the end, it was the renewal of hostilities in 1369, resulting in Calveley's recall, which disrupted this final effort on his part to seek (or more properly, retain) his "castles in Spain." 


The period between the Treaty of Bretigny in 1360 and the resumption of full-scale hostilities nine years later marked a highpoint not only for England, but also for the free companies. Most free company activity merely contributed to the disorders of the age, a fact which led historian Barbara Tuchman to place them among the leading calamities of this most calamitous century. (92)   On the other hand, even such a baleful force as the companies may occasionally produce positive results.  The  growing threat they posed to Avignon seems to have contributed to the papal decision to return to Rome.  Their activities in Northern Italy promoted the success of the house of Visconti.  In Spain, their intervention radically altered the balance of power, ended a decade of war between Aragon and Castile, overthrew the reigning Castilian monarch, and replaced him on the throne with his illegitimate half-brother.  The result was a new, pro-French dynasty which would control Castile and later Aragon and which would survive to merge with the Hapsburgs at the beginning of the sixteenth century. 

The Spanish intervention raises a serious question of just how free the free companies' really were.  The ability of the Black Prince to recall Calveley and his men illustrates the degree to which their actions were dictated by a pre-existing military allegiance.  These events lend weight to the French claim that even in the period of ostensible peace, the English crown retained control over the Anglo-Gascon companies and may even have directed their operations against French territory. 

On the other hand, reaching such a conclusion leaves the historian with an obvious question to which the answer is anything but obvious:  If the English did exercise such influence over their own companies, why did they permit them to take part in the 1366 intervention which was clearly aimed at unseating an English ally and putting in his place a man who had long served French interests? 

The explanation may involve a dramatic reversal in English policy.  In 1366, English leaders may have concluded that by allowing the Anglo-Gascon companies to take part in Enrique's invasion, they could earn some claim on his future neutrality; only to decide in 1367, that this had been a mistake, and that England's interests would be better served by Pedro's restoration.  Although not aluded to by the sources, such a drastic "mid-course correction" would go a long way toward explaining the seemingly inexplicable. 

On the other hand, it is possible that the initial English response to events in Spain was nothing more than a simple miscalculation, in particular, on the part of the Black Prince who was best situated to observe events as they unfolded.  Edward’s failure to keep the Anglo-Gascon companies out of Enrique's expedition may have resulted his seriously misreading the potential consequences. 

In the prince's defense, even the best strategic thinkers of the age would have been hard put to predict just how drastically the free company intervention would alter the Spanish balance.  Little wonder if Edward, always a better tactician than grand strategist, might miscalculate the threat--and then find himself compelled to intervene in order to save a situation for which he was at least partially responsible. 

In the end, however, Edward's ability to shape events south of the Pyrenees was limited not so much by the new military balance established in 1366, but by the nature of his ally, Pedro the Cruel.  Overestimating the finality of their victory at Nájera, Pedro was lulled into believing that he no longer needed the services of those who had made it possible.  This conviction shaped Pedro's subsequent dealings with the English, which in turn, forced Edward to withdraw from the war.  By contrast, Pedro's rival, Enrique, exploited the foreign intervention skillfully enough to win the crown, despite having incurred one of the most disastrous defeats of the fourteenth century. 


Sir Hugh Calveley's military career spanned much of the opening half century of the Hundred Years War.  At the beginning lay an almost unbroken string of English successes, which left half of France under English control.  Then, starting in 1369, came a complete reversal, during which a resurgent France led by Charles V and DuGuesclin dislodged the English from most of their gains. 

Ironically, Calveley's most significant contribution to the war came in Spain, a place far removed from most of his martial activity.  Even more ironically, that contribution benefitted the enemy whom he had fought and would continue to fight throughout his career.  His intervention in 1366 as one of the commanders of the free companies decisively shifted the balance of power on the peninsula against England and placed on the Castilian throne a strongly pro-French monarch, Enrique of Trastámara.  The resulting military alliance with France helped reestablish French naval superiority in the Bay of Biscay and thus played a decisive role in the French victories of the 1370s. 

For his part, Calveley, good "dog of war" that he was and perhaps unaware of the strange role he had played, fought on, as unrelenting during the years of English defeat as he had been in the flood tide of victory. 

(1)  I would like to thank the following individuals and institutions for their assistance and advice during the research and writing of this essay:  the University of Cincinnati Libraries, in particular the reference department and the interlibrary loan and photoduplication services, the British National Library, the Bodleian, Judith Daniels, Kelly DeVries, Dan Gottlieb, Janine Hartman, Donald Kagay, Mark Lause, Sally Moffitt, Norman Murdoch, Jon Nicodemus, Mark DuPuy, Charles Seibert, Ann Twinam, Theresa Vann, Thomas White. I would also like to thank the University of Cincinnati Research Council which has, on several occasions, generously financed my research.  Earlier versions were presented in May, 1999, first at the University College Faculty Forum, and later at the 34rd International Congress on Medieval Studies (Western Michigan University, Kalamazoo, Michigan). 

(2)  Once regarded with skepticism by historians, the ancient tradition of the Combat was substantially borne out by two manuscripts found in the opening decades of the nineteenth century:  one, housed in the Bibliotheque du Roi, contained a near contemporary and rabidly pro-French ballad written by a Breton poet; the other, a missing chapter of Froissart came from the manuscript collection of the Prince de Soubise and supplied a much more balanced account of the event.  English translations of both appear in W. H. Ainsworth, Ballads:  Romantic, Fantastical, and Humorous (New York, n. d. [1874]), pp. 275-326. 

(3)  It was the Breton poet, not Froissart, who actually named Calveley as a participant in the Combat of the Thirty.  While testifying to the occurrence, Froissart fails to list the combattants.  Calveley is introduced by Froissart only when dealing with the events of 1364. 

(4)  Henry D. Sedgwick, The Life of Edward the Black Prince (New York, 1993), p. 267. 

(5)  Fourteenth century sources spell the name it at least eighteen different ways.  This orthographic variability is aptly illustrated in a single volume of papal letters which contains six references to the man—employing six different spellings of his name (Kerverley, Calverlee, Calvyle, Kalvele, Calveley, Calviley, and Calvile). Calendar of Entries in the Papal Registers relating to Great Britain and Ireland [CEPR], pp. 17, 21, 53, 127, 131. Interestingly, the medieval spellings do not seem to include the one frequently used by modern authors, i. e. “Calverley.”  The closest medieval form, “Calveley,” is employed in the Dictionary of National Biography article and has been adopted for use in this article.  For the "modern" spelling, see Sedgwick. 

(6)  Register of Edward the Black Prince (Register), Part III (Palatinate of Chester: 1351-1365) (London, 1932), p. 141, 173. 

(7)  Register, pp. 141, 173.  The importance of royal pardons as an incentive to military service is aptly-illustrated by the scores of pardons issued in 1360 “for good service done in the war of France” to men who had committed such serious crimes as murder, rape, assault, theft, and burglary.  See:  CPR (Edward III: 1358-1361), pp. 375-402. 

(8)  Register, pp. 417, 449. 

(9)  Sir John Froissart, Chronicles of England, France, Spain and the Adjoining Countries, trans. Thomas Johnes, 2 vols., (London, 1857). 

(10)  Thomas Walsingham, Historia Anglicana 2 vols. (London, 1864). 

(11)  After serving the Castilian monarchy throughout the second half of the fourteenth century, Pedro López de Ayala wrote the chronicles of his four royal masters--Pedro I, Enrique II, Juan I, and Enrique III. As a result, this man who had earned renown in his own time as a warrior, politician, and diplomat became as well one of the most important chroniclers of the later Middle Ages.  Ayala’s four chronicles are most readily available in volumes one and two of the Cronicas de Castilla [CRC], which occupy volumes 66 and 68 of the Biblioteca de Autores Españoles [BAE]. 

(12)  A valuable aid to understanding the Breton question is Michael Jones, Ducal Brittany 1364-1399: Relations with England and France during the Reign of Duke John IV (Oxford, 1970). 

(13)  Froissart, 1: 332-334.  Calveley's role in the battle has not gone unrecognized by modern military analysts; see, for example, Charles Oman, A History of the Art of War in the Middle Ages 2 vols.(New York, 1924), 2: 178. 

(14)  Froissart, 1: 404, 411. 

(15)  Froissart 1: 431. Calendar of Inquisitions Miscellaneous (1377-88) (London, 1957), p. 77. 

(16)  Although Froissart fails to mention Calveley's presence in this expedition, we know of it from a document in the Patent Rolls which briefly outlines much of his royal service during the 1370s.  Calendar of the Patent Rolls [CPR] (Richard II: 1377-81) (London, 1895), p. 505. 

(17)  CEPR, Papal Letters (1362-1404) (London, 1902), p. 126-27, 131.  Froissart, I: 496-98.  The advice which, according to Froissart, the royal council gave Charles V on this occasion, sums up superbly the French "Fabian policy" of which the king and his constable were in reality the principal architects: 
Let them [the duke's army] go; by their smoke alone they cannot deprive you of your kingdom:  they will be tired soon, and their force will dissolve away, for as storms and tempests appear sometimes in tremendous forms over a whole country, yet they dissipate of themselves, and no essential harm happens, thus it will befal [sic] these English. 

(18)  His official title was Captain of Calais. Froissart, 1: 510, 513-514.  Walsingham, 1: 344-45, 336. CPR (Edward III: 1374-1377), p. 394; CPR (Richard II: 1377-81), pp. 280, 285, 293, 314; Calendar of Fine Rolls (Edward III: 1368-77) (London, 1924), p. 326;  Calendar of Inquisitions Miscellaneous (1349-77) (London, 1937), p. 357; Calendar of Inquisitions Post Mortem (1-7 Richard II) (London 1970), pp. 5-6. 

(19)  Walsingham, 1: 344. 

(20)  Although Froissart does not name Calveley as being involved in the duke's 1379 expedition, we know of it from two other sources:  the patent rolls and Walsingham's chronicle, the latter treating it in some detail.  CPR (Richard II: 1377-81) (London, 1895), pp. 420-21, 505; Walsingham, 1: 405-06. 

(21)  Froissart, 1: 592. 

(22)  Froissart, 1: 602-618. 

(23)  Froissart, 1: 618-36; CPR (Richard II: 1377-81) (London, 1895), pp. 495, 505. 

(24)  Froissart, 1: 756-759; 2: 1-12. 

(25)  Froissart, 2: 167. 

(26) CPR (Richard II:  1381-85) (London, 1997), pp. 86, 141; Calendar of Close Rolls (Richard II: 1385-89) (London, 1921), p. 119; (Richard II: 1389-92) (London, 1922), p. 178. 

(27)  CPR (Richard II:  1385-89) (London, 1900), p. 254. 

(28)  Although I have not managed to find Calveley's will, the fact that his grand-nephew inherited his worldly goods is stated in the Calendar of Inquisitions Post Mortem (15-23 Richard II) (London, 1970, pp. 242-43. 

(29)  While virtually all chroniclers deal with the problem of the free companies, Froissart shows a particular interest in their activities.  See esp. 1: 292-300, 339-341. 

(30)  G. M. Trevelyan, History of England 4 vols. (Garden City, N. Y., 1953), 1: 301-302. 
(31)  Froissart, 1: 293. 

(32)  Froissart, 1: 294-295. 

(33)  Froissart, 1: 339; Walsingham (London, 1864), 1: 302;    Lettres de Rois, Reines et Autres Personnages des Cours de France et D'Angleterre despuis Louis VII jusqu'a Henry IV, Collection de Documents Inédits sur l'Histoire de France (Paris, 1847), 2:  170-72. 

(34)  Froissart, 1: 339. 

(35)  Froissart, 1: 294. 

(36)  Froissart, 1: 296-97. 

(37)  For an excellent treatment of the companies' activity in Italy, see the article in this collection by William Caferro, "Slaying the Hydra-Headed Beast:  Italy and the Companies of Adventure in the Fourteenth Century." 

(38)  Froissart, 1: 297-99. A good history of the Avignon popes and their policy is G. Mollat, The Popes at Avignon (1305-1378) (New York, 1963):  for Innocent VI, see pp. 44-51. 

(39)  Froissart, 1: 336-339. 

(40)  Mollat, pp. 52-58. 

(41)  ibid. 

(42)  For the chronicle account of Pedro I's reign, see:  Pedro López de Ayala, Crónica del Rey Don Pedro Primero [hereafter abbreviated Ayala], CRC, 1, BAE, 66 (Madrid, 1953), pp. 393-614.  For my own assessment of Pedro and his highly impolitic policies, see:  L. J. Andrew Villalon, "Pedro the Cruel:  Portrait of a Royal Failure," in Medieval Iberia: Essays on the History and Literature of Medieval Spain, ed. Donald J. Kagay and Joseph T. Snow (New York, 1997), pp. 205-216.  See also:  Clara Estow, Pedro the Cruel, 1350-1369 (Leiden, 1995); Helen Nader, The Mendoza in the Spanish Renaissance (Rutgers, New Jersey, 1979). 

(43)  The best historical account of the intervention is P. E. Russell, The English Intervention in Spain & Portugal in the Time of Edward III and Richard II (Oxford University Press, 1955).  See also: Luis Suarez Fernandez, Intervencion de Castilla en la Guerra de los Cien Años (Valladolid, 19  ), chapters 4 and 5. 

(44)  Pere III, Chronicle, trans. Mary Hillgarth (Toronto, 1980), pt. 2:  570-72. 

(45)  Froissart (1: 341) places the number as high as 30,000.  On the other hand, P. E. Russell, citing Ayala, scales the number back by nearly two-thirds, to 10-12,000.  Russell, p. 37. 

(46)  As a result of the “federal” nature of the Aragonese monarchy, he was at the same time Pere III of Catalonia and he was Pedro IV of Aragon.  The use of the Catalan name makes it possible to avoid introducing another Spanish Pedro into the narrative. 

(47)  According to Froissart, DuGuesclin's ransom was set at 100,000 francs, though others name a lower figure, half to be paid by the king of France, the other half jointly  by the king of Aragon and the Count of Trastámara.  Froissart, 1: 341. 

(48)  Froissart, 1: 340-41. 

(49)  Pere III, p. 573.  Ayala, pp. 538, 541. 

(50)  This preliminary diversion led by Calveley, while ignored by both Froissart and Ayala, is mentioned in Pere III's chronicle  (p. 575). 

(51)  Ayala, p. 538. 

(52)  Ayala, p. 53.  The Castilian chronicler indicates his belief that Pedro's decision stemmed from miserliness. 

(53)  Immediately following Peter's flight, Henry entered Burgos in triumph and, at the monastery of Las Huelgas, staged an elaborate coronation. Ayala, pp. 539-41. 

(54)  Ayala, pp. 542-3. 

(55)  Ayala, pp. 545-46. 

(56)  Froissart's exhibits his shaky knowledge of Iberian geography when making the journey through Portugal sound like an afternoon's jaunt.  In fact, the journey required several weeks.  Compare:  Froissart, 1: 342; Ayala, pp. 542-43. 

(57)  While the Chandos herald glosses over opposition to the expedition by Edward's advisers, Froissart asserts that "many of his lords endeavoured to persuade the prince to have nothing to do with the affairs of Don Pedro."   The Chandos herald, Life of the Black Prince (Oxford, 1910); Froissart, 1: 345. 

(58)  The historian is fortunate to have three chronicles written by men who were well-placed in respect to the Spanish intervention.  Two of them (the Chandos herald and Ayala) actually took part in the campaign on opposing sides.  The third (Froissart), while denied permission to accompany the expedition into Spain, was able to interview veterans shortly after their return. 

(59)  Froissart, 1: 349. 

(60)  One large party, trapped in the Basque country, was extricated by Chandos, who had been dispatched for that purpose.   On the march to Bayonne, they mauled a French force sent against them from Narbonne.  Ayala, p. 546; Froissart, 1: 349-54. 

(61)  Ayala, p. 551. 

(62)  Ayala, p. 551; Froissart, 1:  358. 

(63)  Froissart, 1: 348. 

(64)  Ayala, pp. 550-51; Froissart, 1: 348, 357-59, 363.  A commitment to fight on the English side was not kept when Charles the Bad was "captured" by Oliver de Mauny, a relative of Du Guesclin.  He "escaped" from this "captivity" only after the campaign concluded.  Not surprisingly, there was a widespread suspicion, apparently shared by the chroniclers, that Charles arranged for his own abduction in order to avoid having to serve in person on either side. 

(65)  Ayala, p. 553; Chandos herald, p. 156. 

(66)  Ayala, p. 553; Chandos herald, p. 159; Froissart, 1: 367. 

(67)  Chandos herald, p. 158; Froissart, 1: 365-66. 

(68)  Ayala, pp. 553-54; Chandos herald, pp. 158-59; Froissart, 1: 365-67. 

(69)  Chandos herald, p. 159; Froissart, 1: 368. 

(70)  Ayala, p. 554; Chandos herald, pp. 159-60; Froissart, 1: 367-68. 

(71)  Chandos herald, p. 160; Froissart, 1: 368-69. 

(72)  Chandos herald, p. 160; Froissart, pp. 368-69. 

(73)  It is Ayala who mentions Henry's fateful decision to cross the river and deploy on the plain opposite.  Although regarding this (at least in retrospect) as an unwise decision, he attributes it to Henry's courageous and spontaneous nature.    Despite the herald's failure to note the tactical blunder, in speaking of a lengthy pursuit across the plain, his account indirectly supports Ayala.  After all, had Henry not moved his army forward, such a pursuit back to the Najarilla would have been impossible.  Ayala, p. 556. 

(74)  Ayala, p. 552. 

(75)  Chandos herald, pp. 162-63. 

(76)  Ayala, p. 557; Chandos herald, p. 163. 

(77)  The herald and Ayala directly contradict one another on the question of where Calveley fought -- the former places him in the rearguard, the latter in the van with Chandos.  I have accepted the testimony of the herald on this point.  Ayala, p. 557; Chandos herald, p. 163. 

(78)  Chandos herald, p. 163. 

(79)  Chandos herald, p. 163. 

(80)  The fact that Ayala, who fought in the Spanish center under DuGuesclin, placed Calveley opposite him suggests that the Englishman did eventually become involved in the stubborn fighting which took place in the center, leading the Spanish chronicler to assume that he had been with the enemy center from the start. 

(81)  Ayala, p. 557; Chandos herald, p. 164; Froissart, 1: 374. 

(82)  Ayala, pp. 557-58; Chandos herald, p. 164. 

(83)  Ayala, p. 560. 

(84)  Ayala, p. 560. 

(85)  Ayala, pp. 562-7, 575; Froissart, 1: 375-77. 

(86)  Ayala, pp. 57; Chandos herald, p. 166; Froissart 1: 379. 

(87)  The Chandos herald (p. 167) indicates that the symptoms began to appear almost immediately after the expedition's return from Spain. 

(88)  Froissart, 1: 382-83. 

(89)  Froissart, 1: 383-84, 390-400. 

(90)  For information about the "missing" two years, historians interested in Calveley are indebted to Kenneth Fowler who has unearthed a number of documents dating to this period in Barcelona's Archivo de la Corona de Aragon (the AGA).  See: Fowler, "The Wages of War:  The Mercenaries of the Great Companies," in Viajeros, peregrinos, mercaderos en el Occidente Medieval, (Navarre, 1992), pp. 217-241. 

(91)  Fowler’s discovery of the AGA documents clears up a long-standing confusion in Calveley’s biography.  In his History of the Worthies of England, Thomas Fuller cited as one the knight’s five principal accomplishments the fact that he “married the queen of Arragon; which is most certain, her arms being quartered on his tomb.”  The Dictionary of National Biography demurred, endorsing instead the view of several other historians who have argued that the arms of Aragon are not on the tomb and that “It is most probable that he never did marry.”  The documents uncovered by Fowler established that while there was an Aragonese marriage, it involved not the queen, but one of her serving women.  See: Thomas Fuller, The History of the Worthies of England (New York, 1965), p. 274; DNB, Calveley, p. 715. Fowler, p. 237. 

(92)  Barbara W. Tuchman, A Distant Mirror:  The Calamitous Fourteenth Century (New York, 1978).  In fact, Tuchman has good sections on the companies, see pp. 163-67, 222-25.