From satirical Shakespearean plays to romantic stories of outlaws versus evil monarchs, history has not been kind to many of medieval England’s kings. Indeed, reputations were often forged as propaganda by successors legitimising their own regimes.
What were the medieval standards that kings were judged by? Tracts written in the middle ages demanded that kings possess courage, piety, a sense of justice, a listening ear to counsel, restraint with money and the ability to maintain peace.
These qualities reflected the ideals of medieval kingship, but navigating ambitious nobles and European politics was certainly no mean feat. Nonetheless, some kings were evidently better at the job than others.
Here are 5 of England’s medieval kings with the worst reputations. 
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1. John (r. 1199-1216)
Nicknamed ‘Bad King John’, John I acquired a villainous image that has been reproduced time and again in popular culture, including film adaptations of Robin Hood and a play by Shakespeare.
John’s parents Henry II and Eleanor of Aquitaine were formidable rulers and secured England a great deal of French territory. John’s brother, Richard I, despite spending only 6 months in England as king, earned the title of ‘Lionheart’ due to his great military skill and leadership.
This was quite a legacy to live up to, and thanks to Richard’s ongoing holy wars, John also inherited a kingdom whose coffers had been emptied meaning any taxes he raised would have been wildly unpopular.
John had already gained a reputation for treachery prior to becoming king. Then, in 1192, he attempted to seize Richard’s throne while he was held captive in Austria. John even tried to negotiate extending his brother’s imprisonment and he was lucky to be pardoned by Richard after his release.
A poster for Frederick Warde’s production of Runnymede, depicting Robin Hood facing up to the villainous King John, 1895.
Image Credit: Library of Congress / Public Domain
Further damning John in his contemporaries’ eyes was his lack of piety. For medieval England, a good king was a pious one and John had numerous affairs with married noblewomen which was considered deeply immoral. After disregarding the Pope’s nomination for archbishop, he was excommunicated in 1209.
Medieval kings were also meant to be brave. John was nicknamed ‘softsword’ for losing English land in France, including the powerful Duchy of Normandy. When France invaded in 1216, John was almost 3 leagues away by the time any of his men realised he had abandoned them.
Finally, while John was in part responsible for the creation of the Magna Carta, a document widely regarded as the foundation of English justice, his participation was at best unwilling. In May 1215, a group of barons marched an army south forcing John to renegotiate England’s governance, and ultimately, neither side upheld their end of the bargain.
2. Edward II (r. 1307-1327)
Even before he was king, Edward made the medieval royal error of unapologetically surrounding himself with favourites: this meant that throughout his reign, the threat of civil war was ever-present.
Piers Gaveston was Edward’s most notable favourite, so much so that contemporaries described, “two kings reigning in one kingdom, the one in name and the other in deed”. Whether the king and Gaveston were lovers or intimate friends, their relationship enraged the barons who felt slighted by Gaveston’s position.
Edward was forced to exile his friend and institute the Ordinances of 1311, restricting royal powers. Yet at the last minute, he disregarded the Ordinances and brought back Gaveston who was swiftly executed by the barons.
Further damaging his popularity, Edward was determined to pacify the Scots having followed his father on his earlier northern campaigns. In June 1314, Edward marched one of medieval England’s mightiest armies to Scotland but was crushed by Robert the Bruce at the Battle of Bannockburn.
This humiliating defeat was followed by widespread harvest failures and famine. Although not Edward’s fault, the king exacerbated the discontent by continuing to make his closest friends very rich, and in 1321 civil war broke out.
Edward had alienated his allies. His wife Isabella (daughter of the French king) then left for France to sign a treaty. Instead, she plotted against Edward with Roger Mortimer, 1st Earl of March, and together they invaded England with a small army. A year later in 1327, Edward was captured and was forced to abdicate.
3. Richard II (r. 1377-1399)
Son of the Black Prince Edward III, Richard II became king aged 10, so a series of regency councils governed England by his side. Another English king with a poor Shakespearean reputation, Richard was 14 years old when his government brutally suppressed the Peasants’ Revolt of 1381 (though according to some, this act of aggression may have been against teenage Richard’s wishes).
Along with a volatile court full of powerful men wrestling for influence, Richard inherited the Hundred Years’ War with France. War was expensive and England was already heavily taxed. The poll tax of 1381 was the final straw. In Kent and Essex, resentful peasants rose up against landowners in protest.
Aged 14, Richard personally faced the rebels when they arrived in London and allowed them to return home without violence. However, further upheaval in the following weeks saw the rebel leaders executed. 
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The suppression of the revolt during Richard’s reign fed his belief in his divine right as king. This absolutism eventually brought Richard to blows with parliament and the Lords Appellant, a group of 5 powerful nobles (including his own uncle, Thomas Woodstock) who opposed Richard and his influential advisor, Michael de la Pole.
When Richard finally came of age he sought retribution for his counsellors’ earlier betrayals, manifesting in a series of dramatic executions as he purged the Lords Appellant, including his uncle who was accused of treason and executed.
He also sent John of Gaunt’s son (Richard’s cousin) Henry Bolingbroke into exile. Unfortunately for Richard, Henry returned to England to overthrow him in 1399 and with popular support was crowned Henry IV.
4. Henry VI (r. 1422-1461, 1470-1471)
Only 9 months old when he became king, Henry VI had big shoes to fill as the son of the great warrior king, Henry V. As a young king, Henry was surrounded by powerful advisors many of whom he over-generously bestowed riches and titles on, upsetting other nobles.
The young king further split opinion when he married the French king’s niece-in-law, Margaret of Anjou, ceding hard-won territories to France. Coupled with an ongoing unsuccessful French campaign in Normandy, the increasing divide between factions, unrest in the south and the threat of Richard Duke of York’s growing popularity, Henry finally succumbed to mental health issues in 1453.
The first page of Shakespeare’s Henry the Sixth, Part I, printed in the First Folio of 1623.
Image Credit: Folger Shakespeare Library / Public Domain
By 1455, the War of the Roses had begun and during the first battle at St Albans Henry was captured by the Yorkists and Richard ruled as Lord Protector in his stead. Over the following years as the Houses of York and Lancaster struggled for control, the misfortune of Henry’s poor mental health meant he was in little position to take up leadership of armed forces or govern, particularly after the loss of his son and ongoing imprisonment.
King Edward IV took the throne in 1461 but was ejected from it in 1470 when Henry was restored to the throne by the Earl of Warwick and Queen Margaret.
Edward IV defeated the forces of the Earl of Warwick and Queen Margaret at the Battle of Barnet and Battle of Tewkesbury, respectively. Soon after, on 21 May 1471, as King Edward IV paraded through London with Margaret of Anjou in chains, Henry VI died in the Tower of London.
5. Richard III (r. 1483-1485)
Undoubtedly England’s most maligned monarch, Richard came to the throne in 1483 after the death of his brother, Edward IV. Edward’s children were declared illegitimate and Richard stepped in as king with the support of the powerful Duke of Buckingham.
When Richard became king he exhibited some of the desirable traits of a medieval ruler, taking a stance against his brother’s rampant and public adultery and pledging to improve management of the royal court.
However, these good intentions were overshadowed by the mysterious disappearance of his nephews in August 1483. Although there is little concrete evidence to decide his role in the fate of the Princes in the Tower, that Richard had already taken Edward V’s place on the throne was indictment enough.
A Victorian portrayal of Richard III as a scheming hunch-back by Thomas W. Keene, 1887.
Image Credit: University of Illinois at Chicago / Public Domain
Faced with the mammoth task of keeping his crown, Richard planned on marrying Joanna of Portugal and marrying his niece, Elizabeth of York, to Manuel, Duke of Beja. At the time, rumours emerged that Richard in fact planned to marry his niece Elizabeth himself, possibly driving some to side with Richard’s remaining competition for the throne, Henry Tudor.
Henry Tudor, having been in Brittany since 1471, moved to France in 1484. It was there that Tudor amassed a significant invading force which defeated and killed Richard at the Battle of Bosworth in 1485.
