The Hundred Years’ War Revisited: English Blunders in the 14th century

By Andrew Latham and Rand Lee Brown II

“That England, that was wont to conquer others,
Hath made a shameful conquest of itself.
Ah, would the scandal vanish with my life,
How happy then were my ensuing death!”

  ~ William Shakespeare: Richard II, Act II, Scene 1

Perhaps the most remarkable aspect of the Caroline Phase of the Hundred Years War is not so much the successful resurgence of the French under Charles V, but rather the compounded political and strategic failures of England under the aging Edward III and his youthful successor and grandson, Richard II.


What makes this turn all the more puzzling is the fact that it developed immediately after what many in the medieval world believed to be England’s supreme triumph. By 1360, the flower of French chivalry had been repeatedly humiliated by English tactical ingenuity, France herself had been ravaged without mercy, and the French king, Jean II, was in English captivity. So how was it that after this seemingly total victory could England let the initiative slip through its fingers to such a degree that just two decades after the Treaty of Brétigny, the kings of England were farther away from achieving the goal of an English-France than they had ever been?

The answer is a complex and multifaceted one. First, the quality of English leadership began to noticeably deteriorate after 1360. This deterioration, of course, was a gradual process, not immediately apparent even to the most seasoned observers of the war. King Edward III returned to England, basking in an atmosphere of national triumph not known since the days of his grandfather.


Edward is granted Aquitaine by his father King Edward III – British Library, Cotton MS Nero D VI, f.31

His son and possibly most competent military partner, Edward “the Black Prince,” set himself up in Aquitaine as a semi-autonomous sovereign, subordinate only to his father. As we have covered before, it was while ruling as Prince of Aquitaine that he became embroiled in the Castilian Succession Crisis on the side of the problematic and duplicitous Pedro “the Cruel.” England’s intervention in Spain came at a staggering cost with virtually no benefit gained.  Despite suffering a crushing tactical defeat at the hands of the Black Prince at Najera in 1367, the French-backed Enrique de Trastamara ultimately triumphed thanks to having a great deal more popular support in Spain than the vicious and sadistic Pedro.

Although England would continue to attempt to coax Castile into its sphere of influence, such efforts were largely ineffective and almost comically clumsy – like in the futile attempt of another of King Edward’s sons, John of Lancaster, to claim the Castilian throne for himself via his marriage to one of Pedro’s daughters. More importantly, the Castilian adventure bankrupted the Black Prince in Aquitaine, forcing him to substantially raise taxes and thus eroding support for English rule among the native nobility. The inevitable backlash and defection of Aquitainian nobles over to Charles V eventually forced Prince Edward, by then grievously ill with an unknown chronic gastro-intestinal illness that first manifested after his return from Spain, to abandon Aquitaine and return to England in 1371.

In addition to the Black Prince’s failure in Aquitaine and incapacitation through illness, King Edward III’s previously energetic and brilliant style of leadership appeared to gradually slip into complacency and dotage in his old age.  He increasingly withdrew from active leadership in both foreign and domestic affairs, preferring to spend most of his time in comfortable seclusion – especially after the death of his beloved Queen, Philippa, in 1369.  A cadre of sycophants and influencers coalesced around the elderly king, the most notorious of whom was Alice Perrers – Edward’s manipulative favorite mistress almost 40 years his junior that took up with him after his wife’s death. The quality of English government began to noticeably decline in this period, with corruption and self-enrichment rampant among the ruling classes and their administrative servants – so much so that English armies overseas went months without pay and were forced to live off the lands in which they were garrisoned.

However, despite these challenges, English military skill could still produce devastating results in France during this time – like John of Lancaster’s incredible 1373 chevauchée that traversed the entire length of France from Calais to Bordeaux, the longest ever attempted. But the Fabian strategies of Charles V were steadily chipping away at English territories and his superior diplomatic skill was leaving England increasingly more isolated on the geopolitical stage. Finally, the resurgence of French military fortunes coupled with their new-found allies in Castile swung the balance of naval power in the Channel in their favor – English shipping (vital to the domestic economy) was terrorized by Franco-Castilian privateers and several small raiding parties even attacked coastal villages in southern England itself. The war had finally come to England’s shores and the Crown seemed powerless to respond. Parliament, the embodiment of England’s proto-constitutional heritage, began to openly voice its displeasure with the King and those with whom he had surrounded himself.


Just when it seemed matters could get no worse, disaster struck: Edward the Black Prince, the living embodiment of English prowess and seen then as a firm ally of Parliament and the rights of the people, finally succumbed to his debilitating illness in 1376. Crushed by grief, the mighty King Edward fully descended into senility and withdrew from any active role in governing – following his favorite son to the grave a year later. This left England with the child-king Richard II at the head of a government now beset with internal squabbling and the divergent ambitions of various factions.

While John of Lancaster served as a capable regent until his nephew reached his majority, he undercut his own success by developing an elitist animosity for Parliament and especially the Commons – something that would eventually have dire consequences for the realm in 1381. Frustrated by decades of perceived mismanagement at home and abroad, and inflamed by burdensome taxation (especially the hated Poll Tax), the commons of England erupted into open rebellion that year at the instigation of John Ball, a fiery country canon about whom very little is actually known, and Wat Tyler, a rough and boisterous veteran of the wars in France. The rebels scoured the countryside for anyone perceived to be among the “evil councilors” responsible for England’s misfortunes, resorting to spontaneous acts of violence that disturbed even the members of Parliament.

Finally, the rebels occupied London, effectively besieging young King Richard and his court in the Tower of London while running riot throughout the city – hunting down and murdering anyone they deemed an “enemy of the King.” By this time, even the average Englishman had had enough of Tyler and his brigands and were probably relieved to see him unceremoniously slain by the Mayor of London while King Richard bravely dispersed the rest of the mob.


However, young Richard’s reign would never recover from this chaotic beginning and he himself would prove to be a far cry from his more revered forebears, negotiating a disadvantageous truce with France in 1389 at Leulinghem and setting the stage for continued domestic conflict that would eventually result in both his downfall and the continuation of the Hundred Years War.

Further Reading:

Jones, Dan, Summer of Blood – England’s First Revolution (Penguin Books, 2010)

Jones, Michael, The Black Prince – England’s Greatest Medieval Warrior (Pegasus Books, 2018)

Dr. Andrew Latham is a professor of political science at Macalester College in Saint Paul, Minnesota. He is the author, most recently, of a monograph entitled Medieval Sovereignty, to be published in 2020 by ARC Humanities Press.  You can visit Andrew’s website at or follow Andrew on Twitter @aalatham

Capt Rand Lee Brown II is a commissioned officer in the United States Marine Corps currently assigned to Marine Forces Reserve.  Holding a Master of Arts degree in Military History from Norwich University with a focus on medieval warfare, Capt Brown has written on military history for a variety of forums, including the Marine Corps Gazette and

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Top Image: Battle in the late 14th century – BL Royal 20 C VII Fol. 35