In October 1216, a stricken king was dragged through the English countryside, his body ravaged by dysentery. He had spent years alienating his nobles, losing his family’s vast empire, and fighting a brutal civil war against his own barons. Now, as his strength failed, he was carried to Newark Castle in Nottinghamshire, where his body finally gave out. King John, one of the most despised monarchs England has ever known, was dead.

And his reign, which had begun with so much potential and ended in disaster, was finally over. John had not been born to rule. He was the fourth and youngest son of King Henry II, who presided over the Angevin Empire, a sprawling domain that included England and nearly half of France. His mother was the formidable Eleanor of Aquitaine.
But despite having two of the most powerful parents in Europe, John grew up in one of the most dysfunctional families in history. His older brothers, Henry, Richard, and Geoffrey, stood to inherit great power and wealth. There was little left for the youngest son, but John had something else going for him: a cunning and ruthless mind. Henry II did not trust his elder sons and refused to grant them real power.
As they grew older, they chafed under his restrictions. By the time John was a boy, the Angevin Empire was a den of infighting and backstabbing. Henry gave young John control over several powerful castles across France, and one person in particular was furious about it: John’s older brother, Henry the Young King. Henry had been promised those castles himself, and he feared his father would give even more of his lands to John.
So he revolted against his father, and he was not alone. Eleanor of Aquitaine, unhappy with her husband’s meddling in her own territories, pushed John’s other brothers to join forces against their father. The family was in complete disarray, and no one had more to gain than John. He remained at his father’s side as the final loyal son, and the longer the rebellion dragged on, the more lands Henry II gave to him, mostly by ripping them away from various nobles.
The Earl of Gloucester was one of the richest men in England, and he planned to split his lands among his many daughters. Henry had other ideas. He disinherited all of the earl’s daughters except one, Isabella, and betrothed her to John, setting him up to become one of the richest men in the empire. The two were children at the time and related through their great-grandfather, making the marriage technically illegal on grounds of consanguinity.
The Archbishop of Canterbury banned the match, but Henry II took his case to the pope, who allowed the marriage under one condition: the couple were forbidden from sleeping together. John was the medieval equivalent of a spoiled millionaire’s son. He adored books and maintained an incredibly expensive library that traveled with him. He collected jewels and fine clothes.
Anyone who knew him quickly realized something was off. His mood swings were violent, he was extremely touchy and jealous, and he was prone to sudden fits of rage. Those who witnessed his anger noted that he would often gnaw on his own fingers in blind fury. Beneath the fine clothes and wild mood swings, however, lay a cunning and ruthless mind, and that made him extremely dangerous.
The constant infighting among John’s family soon claimed its first victim. John’s oldest brother, Henry the Young King, started a war with Richard over one slight or another, but he bit off more than he could chew. The conflict accomplished little, and Henry died an agonizing death from dysentery. With the primary heir gone, everyone moved up in the line of succession.
Henry II made Richard the king of England and gave John Richard’s old territory of Aquitaine. Richard was not about to give up a region as rich as Aquitaine easily, so he refused to budge. Furious, Henry ordered John and his brother Geoffrey to take the duchy from Richard by force. John and Geoffrey stormed the capital at Poitiers, and Richard responded by attacking Geoffrey’s territory in Brittany.
The family was a total mess, but after years of scheming and fighting, they were finally getting sick of it. The conflict reached a stalemate, and the family met in England to call a truce. Richard kept Aquitaine, but John, now a temperamental teenager, got his first taste of real power, and he liked it. Henry II still wanted to secure serious land for his favorite son, so he turned to Ireland.
He sent John and a large entourage to the Emerald Isle to start ruling there. John had real power at last, and he completely screwed it up. The Angevins had only recently conquered Ireland, and the Irish were not happy about it. It would take a delicate hand to secure control, and John was more like a bull in a china shop.
He lasted a year in Ireland, and in that time he managed to anger the locals, alienate nearly all his Angevin allies, and lose ground to Irish rebels. He eventually slunk back to England with his tail between his legs, placing the blame entirely on his viceroy, Hugh de Lacy. It was the beginning of a lifetime of failures. Henry II grew old and weak, and John’s brother Richard saw blood in the water.
He allied with King Philip II of France and declared war on his stumbling father. In a shocking twist, John, after a lifetime as his father’s loyal servant, turned coat and sided with Richard. Henry II had no fight left in him. He surrendered, accepted Richard’s demands, and died soon after.
Richard became the new king, and he had only one thing on his mind: the Crusades. He desperately wanted to fight in the Holy Land, but he knew it was risky. He had spent his entire life squabbling with his family over the Angevin Empire, and he realized someone might seize it as soon as he left. To buy John’s loyalty, Richard showered him with valuable territories, including Cornwall, Devon, Somerset, and Nottingham.
He hoped that with all that wealth, John would sit by and watch over the empire in his name. Richard named his four-year-old nephew Arthur as his heir and forced John to promise not to set foot in England for three years. That, he thought, gave him plenty of time to go on crusade and return to reclaim his throne. John happily agreed.
He would never dare to usurp his brother’s throne, of course. It did not take long for John to get to work. He knew the people of England were unhappy with Richard’s rule, and he saw his chance to strike. He convinced his mother, Eleanor, to persuade Richard to let him back into England.
Richard relented, and John quickly crossed the Channel, establishing himself at the royal court. The years passed, yet Richard, the supposed king of England, remained nowhere to be found. People in England began to see John as their de facto ruler, perhaps even the next king. John started spreading rumors that Richard had been killed on crusade.
But Richard was still alive and had begun his trip back home when Duke Leopold of Austria captured him and handed him over to the Holy Roman Emperor, Henry VI. It was the best opportunity John would ever get. In England, the lines were drawn between those who supported Richard and those who backed John. Fighting broke out and turned ugly.
Even with Richard in captivity, John could not gain a foothold against the forces loyal to his brother. By the time Richard escaped and limped back to England, John had accomplished nothing. His forces surrendered almost the second Richard stepped foot on English soil. John ran away to Normandy and tried to lie low.
Richard caught up with him eventually, but his response surprised everyone. The fierce crusader king forgave his 27-year-old brother, saying he was only a child who had evil counselors. After his laughable failed coup, John bided his time and waited for his next chance to strike. It came when Richard took a crossbow bolt to the shoulder.
The wound festered, and the warrior king quickly faded away. He died in 1199, leaving a power vacuum behind. There were two claimants to the throne: John and his nephew Arthur, still a young boy. Norman law favored John, while Angevin law favored Arthur.
Within months, the succession crisis broke out into open conflict. John negotiated a peace with King Philip of France, who recognized John as Richard’s heir. In return, John accepted Philip as the feudal overlord of his territories in France. The weak diplomacy disgusted the Normans, who took to calling the new king John Softsword.
Just when things seemed as bad as they could get, John set his sights on replacing his wife. His new love interest was also named Isabella, Isabella of Angoulême. Contemporary chroniclers noted she was too young even for the standards of the time. The problem was that Isabella was already engaged to Hugh the 9th of Lusignan, a powerful noble and a political rival of John’s.
Hugh took his case to King Philip of France, who ordered John to come to Paris and answer for his actions. John refused and stayed put with his child bride. Philip was fed up with John’s nonsense, so he revoked John’s claim to all his territories on the continent, including his ancestral home of Normandy. King John found himself at war once again, fighting for his birthright, all because he wanted to marry one particular young girl.
John’s nephew Arthur was still a rival claimant to the throne, so John decided to take him out of the equation. He had Arthur captured, locked him up, and threw away the key. No one ever saw Arthur again. Modern historians believe John had him killed and his body thrown into the Seine.
In 1204, John received devastating news: his mother, Eleanor of Aquitaine, had died. Her steely grip on Aquitaine had been essential to his rule. King Philip went for the jugular. In one fell swoop, he invaded and claimed Normandy, Anjou, and Poitou.
All that remained of the once formidable Angevin Empire was England and Aquitaine. Philip defeated John’s forces, and John had to sign a humiliating peace treaty, putting the final nail in the coffin of his hopes of regaining his territory. Back in England, things went from bad to worse. Rebel barons, thoroughly fed up with the tyrannical king, raised a force of their own and marched on London.
They easily took the city, and several nobles loyal to John betrayed him and joined the rebels. Completely out of options, John had to wave the white flag and sign one of the most humiliating deals in English history. The barons forced him to sign the Magna Carta, which hamstrung his power and granted the barons untold freedoms. It should have been rock bottom, but the Magna Carta actually accomplished little.
Neither John nor the barons abided by it, and it was only a matter of time before they ripped it up and settled things the old-fashioned way. The rebels gathered a new army and planned to oust John by force. In a shocking move, they invited the French Prince Louis to lead them. Even a French king would be better than King John at this point.
The First Barons’ War was a miserable end to a miserable reign. The two sides fought each other to a stalemate that showed little sign of letting up. Stubborn John insisted on leading his men from the front lines, and that eventually proved fatal. He contracted dysentery, yet he still trudged through the countryside, determined to deal with the rebel barons once and for all.
Dysentery is an extremely gruesome way to go, a fitting end to John’s horrible reign. He managed to limp into Newark Castle before his body finally gave out. He died in October 1216, just over a year after he signed the Magna Carta. For the final decade of his reign, John had kept his own niece Eleanor rotting in a cell because she had a claim to his throne.
In a final act of spite, he amended his will to state that she would never be released from captivity. That was the kind of man King John was. History remembers him as one of the most despised monarchs England has ever seen, a title he truly earned.