The history of medieval England is filled with kings who ruled, but also with men who came remarkably close to the throne. Some died unexpectedly, others were overthrown, and a few were only a single battle away from becoming king. Here are ten men who nearly ruled England during the Middle Ages.
1. Edward the Exile
Edward the Exile depicted on a 13th-century genealogical scroll – British Library Royal MS 14 B V
Edward was only a few months old when his father, King Edmund Ironside, died in 1016 after a brief struggle for the English throne against Cnut the Great. To remove any potential rivals, Cnut ordered that Edward and his brother Edmund be sent abroad with instructions that they be killed. Instead, the children were spared. They were first taken to Sweden and then secretly sent to the court of Kyiv, where they found protection under the ruler Yaroslav the Wise. Eventually the brothers made their way to Hungary, where Edward spent most of his life in exile and married a Hungarian noblewoman named Agatha.
Decades later, King Edward the Confessor learned that his long-lost nephew was still alive. With no children of his own, the king invited Edward back to England in 1057 and apparently intended to make him his heir. However, Edward the Exile died suddenly only two days after arriving in England, under circumstances that remain unclear and have sometimes been suspected to involve foul play. His young son, Edgar the Ætheling, would later become another almost-king: after the death of Harold Godwinson at the Battle of Hastings in 1066, Edgar was proclaimed king in London, but he never managed to secure the throne and soon submitted to William the Conqueror.
2. Robert Curthose
Robert Curthose is taken captive by his brother Henry – BnF, Français 230 fol.255
Robert Curthose was the eldest son of William the Conqueror and, for many years, seemed destined to inherit much of his father’s vast domains. However, relations within the royal family were often tense. According to one story, Robert’s younger brothers, William Rufus and Henry, once poured a chamber pot over his head as a joke, an insult that helped spark a serious quarrel. Robert eventually rebelled against his father and fought against him in Normandy. During one clash he even wounded William in battle, only realizing afterwards that he had nearly killed his own father.
When William the Conqueror died in 1087, his lands were divided. Robert received the Duchy of Normandy, while William Rufus became King of England. Robert later joined the First Crusade and gained a reputation as a brave and capable knight. While he was away, however, events in England moved against him. William Rufus died in a hunting accident in 1100, and their younger brother Henry quickly seized the throne to become Henry I. Robert attempted to challenge Henry’s rule, but the struggle ended with his defeat and capture at the Battle of Tinchebray in 1106. He spent the rest of his life imprisoned, dying in 1134 after nearly three decades in captivity.
3. William Adelin
Detail of the wreck of the White Ship, British Library MS Cotton Claudius D. ii, f. 45v.
William Adelin was the only legitimate son of King Henry I of England and was widely expected to succeed his father. Born around 1103, he was formally recognized as heir to both England and the Duchy of Normandy. Henry arranged homage to him from Norman and English nobles, and William was already being prepared for rulership while still a teenager. By 1120 he had travelled to Normandy with his father, strengthening his position as the future ruler of Henry’s Anglo-Norman realm.
Tragedy struck on the night of 25 November 1120, when William boarded the White Ship along with many young nobles and members of the royal household. With many of the passengers and crew reportedly drunk, the ship crashed into a submerged rock shortly after leaving the harbour of Barfleur. As the vessel sank, William managed to escape briefly in a small boat. However, when he heard his half-sister Matilda crying out for help, he ordered the boat to turn back. As it approached the wreck, desperate survivors tried to climb aboard, causing the boat to capsize. William drowned along with hundreds of others. The disaster left Henry I without a legitimate male heir and helped trigger the long civil war in England when Stephen took the crown.
4. Eustace IV
Meeting of Stephen and Prince Henry at Wallingford (Cassell’s Illustrated History of England, 1865), depicting the Treaty of Wallingford, 1153. Eustace, then in his early 20s, is standing at left, his arm resting on his shield, his father next to him.
Eustace IV, Count of Boulogne, was the eldest son of King Stephen of England and his wife Matilda of Boulogne. During the civil war known as the Anarchy (1135–1153), Stephen attempted to secure the succession for his son. In 1149 Eustace was recognised as heir by many of Stephen’s supporters, and his father even tried to have him crowned during his own lifetime in the same way that Henry the Young King would later be crowned by Henry II. However, this effort failed when the Archbishop of Canterbury refused to perform the coronation without the approval of the papacy.
Contemporary chroniclers did not speak well of Eustace. The Peterborough Chronicle, for example, says, “He was an evil man and did more harm than good wherever he went; he spoiled the lands and laid thereon heavy taxes.” His sudden death in 1153 dramatically changed the political situation in England. Soon afterwards Stephen agreed to the Treaty of Wallingford, which ended the civil war by recognising Henry of Anjou—his rival’s son—as his successor. When Stephen died the following year, Henry became King Henry II, beginning the Plantagenet dynasty.
5. Henry the Young King
Coronation of Henry the Young King, c. 1220-1240, The Becket Leaves, France. Wikimedia Commons
Henry the Young King was the eldest surviving son of King Henry II of England and Eleanor of Aquitaine. In an unusual move intended to secure the succession, Henry II had his son crowned as a junior or “associate” king in 1170 while he was still alive. Although Henry the Young King held the title of king and was crowned again in 1172, he was never given real authority to rule. Instead, he became famous for his love of tournaments and knightly display. A poet of his time praised him as “the best king who ever took up a shield, the most daring and best of all tourneyers.”
Frustrated by his lack of power, Henry joined a major rebellion against his father in 1173, supported by several powerful nobles and even encouraged by his mother. Although the revolt failed, tensions within the royal family continued. In 1183, while campaigning against his brother Richard in Aquitaine, Henry suddenly fell ill, likely with dysentery. He died at the age of 28 before ever ruling independently. When Henry II heard the news, he reportedly lamented, “He cost me much, but I wish he had lived to cost me more.” Henry’s death changed the line of succession, eventually allowing his brother Richard to become King Richard I.
6. Arthur of Brittany
Arthur of Brittany paying homage to Philip II of France. Chroniques de St Denis, British Library.
Arthur of Brittany was the son of Geoffrey, Duke of Brittany, the fourth son of King Henry II of England. Because Geoffrey died before his father, Arthur grew up as the nephew of King Richard I. For much of Richard’s reign, Arthur was treated by some as the likely heir, particularly among supporters in France and Brittany who believed he had a stronger hereditary claim than Richard’s younger brother John. However, when Richard was mortally wounded during the siege of Châlus in 1199, the situation changed quickly. John moved to secure the throne, and many English and Norman nobles backed him instead of the young Arthur, who was only twelve years old.
Arthur did not give up his claim. With the support of King Philip II of France, he rebelled against John and attempted to challenge him in Normandy. In 1202 Arthur was captured by John’s forces during the siege of Mirebeau and imprisoned. What happened next remains one of the great mysteries of medieval English history. Arthur disappeared while in captivity, and many contemporaries believed that John had him murdered. One chronicler wrote: “After King John had captured Arthur and kept him alive in prison for some time, at length, in the castle of Rouen, after dinner on the Thursday before Easter, when he was drunk and possessed by the devil, he slew him with his own hand, and tying a heavy stone to the body cast it into the Seine.” Arthur’s death deeply damaged John’s reputation and helped turn many of his supporters against him.
7. Louis VIII
Arrival of Louis of France in England, from the Chronica Majora, by Matthew Paris
During the troubled reign of King John, many English barons became deeply dissatisfied with their ruler. After John’s conflicts with the nobility led to the First Barons’ War, a group of rebel barons took the extraordinary step of inviting Prince Louis of France—the son of King Philip II—to claim the English throne. In 1216 Louis landed in England with a French army and quickly gained support. London opened its gates to him, and many leading barons swore allegiance. Within weeks Louis controlled large parts of southeastern England and appeared well on his way to becoming king.
However, events soon turned against him. King John died suddenly in October 1216, leaving the throne to his nine-year-old son, Henry III. Many barons who had supported Louis switched sides, believing it better to back a child king than allow a French prince to rule England. Louis suffered important defeats the following year, first at the Battle of Lincoln in May 1217 and then when his fleet was defeated at the naval Battle of Sandwich. With his position collapsing, Louis agreed to withdraw from England in return for compensation. Although he never became king of England, he would later rule France as Louis VIII from 1223 to 1226.
8. Alphonso, Earl of Chester
Alphonso depicted in a 14th-century genealogical role -British Library Royal MS 14 B VI
Alphonso was the eldest son of King Edward I of England and his wife Eleanor of Castile, and for many years he was expected to inherit the English throne. Born in 1273 while his parents were travelling in the Mediterranean during the Ninth Crusade, he was named after his godfather, King Alfonso X of Castile. As the royal heir, Alphonso was given several titles and estates while still a child, including the earldom of Chester, which was traditionally associated with the king’s eldest son. Like many medieval princes, he was also involved in diplomatic plans for marriage, and at the age of ten he was engaged to Margaret, the daughter of Floris V, Count of Holland.
Alphonso’s life, however, was cut short. In August 1284, at the age of ten, he died unexpectedly at Windsor Castle. His death ended the planned marriage alliance and forced Edward I to reconsider the succession. The king’s next surviving son, Edward of Caernarfon, now became heir to the throne. When Edward I died in 1307, that younger son would become King Edward II. Alphonso’s early death therefore played an important role in shaping the later history of medieval England, as Edward II’s troubled reign would lead to rebellion, deposition, and eventual murder.
9. Edward the Black Prince
Edward the Black Prince
Edward, known to history as the Black Prince, was the eldest son of King Edward III and for many years seemed certain to inherit the English throne. From a young age he played a prominent role in the early stages of the Hundred Years War against France. He won fame as a military commander, particularly at the Battle of Crécy in 1346 and the Battle of Poitiers in 1356, where his forces captured the French king, John II. These victories made him one of the most celebrated warriors of his generation and a symbol of English chivalry.
Despite his fame, Edward never became king. During his later years he suffered from serious illness, possibly contracted during his campaigns in Spain. His health steadily declined during the 1370s, and he died in 1376 at the age of 45, one year before his father. Because of his death, the English crown passed instead to his ten-year-old son, who became King Richard II in 1377. The accession of such a young king would later contribute to political tensions and instability within England.
10. Edward of Westminster
Drawing of Edward from the Beauchamp Pageant, c. 1483–1494
Edward of Westminster was the only son of King Henry VI and Margaret of Anjou, and during the Wars of the Roses he stood at the centre of the Lancastrian claim to the English throne. Born in 1453, he became Prince of Wales shortly afterwards, but his early life was shaped by the political turmoil surrounding his father’s weak rule and periods of mental illness. As the conflict between the rival houses of Lancaster and York intensified, Edward was raised largely under the protection and guidance of his formidable mother, who led the Lancastrian cause during many of the war’s most difficult years.
In 1471, at the age of seventeen, Edward took part in the Lancastrian campaign to restore his father to the throne. He fought with the Lancastrian army at the Battle of Tewkesbury in May of that year, one of the decisive battles of the Wars of the Roses. The Yorkists won a crushing victory, and Edward was killed shortly afterwards. Some accounts claim he died fighting during the battle, while others suggest he was captured and executed after being brought before the victorious Yorkist leaders. His death ended the direct Lancastrian line of succession and marked a turning point in the long struggle for control of the English crown.
Medieval succession was often far less predictable than it might appear in hindsight. Illness, accidents, rebellions, and battlefield deaths repeatedly reshaped the line of inheritance. Had even one of these men lived longer or secured victory at the right moment, the history of England—and perhaps even Europe—might have taken a very different course.
The history of medieval England is filled with kings who ruled, but also with men who came remarkably close to the throne. Some died unexpectedly, others were overthrown, and a few were only a single battle away from becoming king. Here are ten men who nearly ruled England during the Middle Ages.
1. Edward the Exile
Edward was only a few months old when his father, King Edmund Ironside, died in 1016 after a brief struggle for the English throne against Cnut the Great. To remove any potential rivals, Cnut ordered that Edward and his brother Edmund be sent abroad with instructions that they be killed. Instead, the children were spared. They were first taken to Sweden and then secretly sent to the court of Kyiv, where they found protection under the ruler Yaroslav the Wise. Eventually the brothers made their way to Hungary, where Edward spent most of his life in exile and married a Hungarian noblewoman named Agatha.
Decades later, King Edward the Confessor learned that his long-lost nephew was still alive. With no children of his own, the king invited Edward back to England in 1057 and apparently intended to make him his heir. However, Edward the Exile died suddenly only two days after arriving in England, under circumstances that remain unclear and have sometimes been suspected to involve foul play. His young son, Edgar the Ætheling, would later become another almost-king: after the death of Harold Godwinson at the Battle of Hastings in 1066, Edgar was proclaimed king in London, but he never managed to secure the throne and soon submitted to William the Conqueror.
2. Robert Curthose
Robert Curthose was the eldest son of William the Conqueror and, for many years, seemed destined to inherit much of his father’s vast domains. However, relations within the royal family were often tense. According to one story, Robert’s younger brothers, William Rufus and Henry, once poured a chamber pot over his head as a joke, an insult that helped spark a serious quarrel. Robert eventually rebelled against his father and fought against him in Normandy. During one clash he even wounded William in battle, only realizing afterwards that he had nearly killed his own father.
When William the Conqueror died in 1087, his lands were divided. Robert received the Duchy of Normandy, while William Rufus became King of England. Robert later joined the First Crusade and gained a reputation as a brave and capable knight. While he was away, however, events in England moved against him. William Rufus died in a hunting accident in 1100, and their younger brother Henry quickly seized the throne to become Henry I. Robert attempted to challenge Henry’s rule, but the struggle ended with his defeat and capture at the Battle of Tinchebray in 1106. He spent the rest of his life imprisoned, dying in 1134 after nearly three decades in captivity.
3. William Adelin
William Adelin was the only legitimate son of King Henry I of England and was widely expected to succeed his father. Born around 1103, he was formally recognized as heir to both England and the Duchy of Normandy. Henry arranged homage to him from Norman and English nobles, and William was already being prepared for rulership while still a teenager. By 1120 he had travelled to Normandy with his father, strengthening his position as the future ruler of Henry’s Anglo-Norman realm.
Tragedy struck on the night of 25 November 1120, when William boarded the White Ship along with many young nobles and members of the royal household. With many of the passengers and crew reportedly drunk, the ship crashed into a submerged rock shortly after leaving the harbour of Barfleur. As the vessel sank, William managed to escape briefly in a small boat. However, when he heard his half-sister Matilda crying out for help, he ordered the boat to turn back. As it approached the wreck, desperate survivors tried to climb aboard, causing the boat to capsize. William drowned along with hundreds of others. The disaster left Henry I without a legitimate male heir and helped trigger the long civil war in England when Stephen took the crown.
4. Eustace IV
Eustace IV, Count of Boulogne, was the eldest son of King Stephen of England and his wife Matilda of Boulogne. During the civil war known as the Anarchy (1135–1153), Stephen attempted to secure the succession for his son. In 1149 Eustace was recognised as heir by many of Stephen’s supporters, and his father even tried to have him crowned during his own lifetime in the same way that Henry the Young King would later be crowned by Henry II. However, this effort failed when the Archbishop of Canterbury refused to perform the coronation without the approval of the papacy.
Contemporary chroniclers did not speak well of Eustace. The Peterborough Chronicle, for example, says, “He was an evil man and did more harm than good wherever he went; he spoiled the lands and laid thereon heavy taxes.” His sudden death in 1153 dramatically changed the political situation in England. Soon afterwards Stephen agreed to the Treaty of Wallingford, which ended the civil war by recognising Henry of Anjou—his rival’s son—as his successor. When Stephen died the following year, Henry became King Henry II, beginning the Plantagenet dynasty.
5. Henry the Young King
Henry the Young King was the eldest surviving son of King Henry II of England and Eleanor of Aquitaine. In an unusual move intended to secure the succession, Henry II had his son crowned as a junior or “associate” king in 1170 while he was still alive. Although Henry the Young King held the title of king and was crowned again in 1172, he was never given real authority to rule. Instead, he became famous for his love of tournaments and knightly display. A poet of his time praised him as “the best king who ever took up a shield, the most daring and best of all tourneyers.”
Frustrated by his lack of power, Henry joined a major rebellion against his father in 1173, supported by several powerful nobles and even encouraged by his mother. Although the revolt failed, tensions within the royal family continued. In 1183, while campaigning against his brother Richard in Aquitaine, Henry suddenly fell ill, likely with dysentery. He died at the age of 28 before ever ruling independently. When Henry II heard the news, he reportedly lamented, “He cost me much, but I wish he had lived to cost me more.” Henry’s death changed the line of succession, eventually allowing his brother Richard to become King Richard I.
6. Arthur of Brittany
Arthur of Brittany was the son of Geoffrey, Duke of Brittany, the fourth son of King Henry II of England. Because Geoffrey died before his father, Arthur grew up as the nephew of King Richard I. For much of Richard’s reign, Arthur was treated by some as the likely heir, particularly among supporters in France and Brittany who believed he had a stronger hereditary claim than Richard’s younger brother John. However, when Richard was mortally wounded during the siege of Châlus in 1199, the situation changed quickly. John moved to secure the throne, and many English and Norman nobles backed him instead of the young Arthur, who was only twelve years old.
Arthur did not give up his claim. With the support of King Philip II of France, he rebelled against John and attempted to challenge him in Normandy. In 1202 Arthur was captured by John’s forces during the siege of Mirebeau and imprisoned. What happened next remains one of the great mysteries of medieval English history. Arthur disappeared while in captivity, and many contemporaries believed that John had him murdered. One chronicler wrote: “After King John had captured Arthur and kept him alive in prison for some time, at length, in the castle of Rouen, after dinner on the Thursday before Easter, when he was drunk and possessed by the devil, he slew him with his own hand, and tying a heavy stone to the body cast it into the Seine.” Arthur’s death deeply damaged John’s reputation and helped turn many of his supporters against him.
7. Louis VIII
During the troubled reign of King John, many English barons became deeply dissatisfied with their ruler. After John’s conflicts with the nobility led to the First Barons’ War, a group of rebel barons took the extraordinary step of inviting Prince Louis of France—the son of King Philip II—to claim the English throne. In 1216 Louis landed in England with a French army and quickly gained support. London opened its gates to him, and many leading barons swore allegiance. Within weeks Louis controlled large parts of southeastern England and appeared well on his way to becoming king.
However, events soon turned against him. King John died suddenly in October 1216, leaving the throne to his nine-year-old son, Henry III. Many barons who had supported Louis switched sides, believing it better to back a child king than allow a French prince to rule England. Louis suffered important defeats the following year, first at the Battle of Lincoln in May 1217 and then when his fleet was defeated at the naval Battle of Sandwich. With his position collapsing, Louis agreed to withdraw from England in return for compensation. Although he never became king of England, he would later rule France as Louis VIII from 1223 to 1226.
8. Alphonso, Earl of Chester
Alphonso was the eldest son of King Edward I of England and his wife Eleanor of Castile, and for many years he was expected to inherit the English throne. Born in 1273 while his parents were travelling in the Mediterranean during the Ninth Crusade, he was named after his godfather, King Alfonso X of Castile. As the royal heir, Alphonso was given several titles and estates while still a child, including the earldom of Chester, which was traditionally associated with the king’s eldest son. Like many medieval princes, he was also involved in diplomatic plans for marriage, and at the age of ten he was engaged to Margaret, the daughter of Floris V, Count of Holland.
Alphonso’s life, however, was cut short. In August 1284, at the age of ten, he died unexpectedly at Windsor Castle. His death ended the planned marriage alliance and forced Edward I to reconsider the succession. The king’s next surviving son, Edward of Caernarfon, now became heir to the throne. When Edward I died in 1307, that younger son would become King Edward II. Alphonso’s early death therefore played an important role in shaping the later history of medieval England, as Edward II’s troubled reign would lead to rebellion, deposition, and eventual murder.
9. Edward the Black Prince
Edward, known to history as the Black Prince, was the eldest son of King Edward III and for many years seemed certain to inherit the English throne. From a young age he played a prominent role in the early stages of the Hundred Years War against France. He won fame as a military commander, particularly at the Battle of Crécy in 1346 and the Battle of Poitiers in 1356, where his forces captured the French king, John II. These victories made him one of the most celebrated warriors of his generation and a symbol of English chivalry.
Despite his fame, Edward never became king. During his later years he suffered from serious illness, possibly contracted during his campaigns in Spain. His health steadily declined during the 1370s, and he died in 1376 at the age of 45, one year before his father. Because of his death, the English crown passed instead to his ten-year-old son, who became King Richard II in 1377. The accession of such a young king would later contribute to political tensions and instability within England.
10. Edward of Westminster
Edward of Westminster was the only son of King Henry VI and Margaret of Anjou, and during the Wars of the Roses he stood at the centre of the Lancastrian claim to the English throne. Born in 1453, he became Prince of Wales shortly afterwards, but his early life was shaped by the political turmoil surrounding his father’s weak rule and periods of mental illness. As the conflict between the rival houses of Lancaster and York intensified, Edward was raised largely under the protection and guidance of his formidable mother, who led the Lancastrian cause during many of the war’s most difficult years.
In 1471, at the age of seventeen, Edward took part in the Lancastrian campaign to restore his father to the throne. He fought with the Lancastrian army at the Battle of Tewkesbury in May of that year, one of the decisive battles of the Wars of the Roses. The Yorkists won a crushing victory, and Edward was killed shortly afterwards. Some accounts claim he died fighting during the battle, while others suggest he was captured and executed after being brought before the victorious Yorkist leaders. His death ended the direct Lancastrian line of succession and marked a turning point in the long struggle for control of the English crown.
Medieval succession was often far less predictable than it might appear in hindsight. Illness, accidents, rebellions, and battlefield deaths repeatedly reshaped the line of inheritance. Had even one of these men lived longer or secured victory at the right moment, the history of England—and perhaps even Europe—might have taken a very different course.
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