The 5 Greatest Medieval Kings in History

Find out what made these monarchs the 5 greatest medieval kings of all time!

Jan 24, 2023By Chester Ollivier, BA (Hons) History
greatest medieval kings


Throughout the medieval era, many factors determined how successful a king was. For instance, if a ruler was successful in warfare, he was guaranteed to be remembered as a great medieval king. In addition, if a king was pious, or deeply religious, he was also considered a success; speaking out against a senior religious figure would have been almost on par with blasphemy. These five medieval kings below fit the criteria, and that is why they have made the shortlist of the greatest medieval kings of all time.


1. The Medieval King Who Took the Cross: Richard I of England (1189-99)

medieval king richard i
Effigy of Richard the Lionheart at Fontevraud Abbey, photograph by Adam Bishop, 17 October 2011, via Wikimedia Commons


Richard I of England, better known as Richard the Lionheart, was king of England for just ten years, from 1189-99. Yet he is still one of the most famous medieval kings of all time. Born on the 8th of September 1157, Richard was the eldest surviving son of Henry II of England and his wife, Eleanor of Aquitaine. During his early childhood, Eleanor and Henry had become estranged from one another, and as a result, Richard spent the majority of his early years in France with his mother. Richard spoke French and became accustomed to French culture. In 1172, he was made Duke of Aquitaine and became acquainted with the French heir to the throne, Philip Augustus.


By 1180, Philip had been crowned as King Philip II of France, and just seven years later, the pair’s friendship would be put through a serious test: the onset of the Third Crusade. Richard was the first European noble to “take the cross” — a term given to those who had given their crusading vows to recover Jerusalem for Christendom and take it out of the Muslim Saladin’s hands.


However, Richard was unable to go out on crusade as soon as he wanted to. His father had died, and Richard was thus crowned as King Richard I of England — which delayed his crusading journey. He did not actually set out on crusade until July 1190 — ten months after his coronation as king of England. Both Richard and Philip set out on crusade together; two huge medieval kings going to fight for their countries was a sight admired by many in both England and France.


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Philip (center) and Richard (left) accepting the keys to Acre, from Grandes Chroniques de France, c. 1375-80, via Gallica Digital Library

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Richard also made important alliances across Europe on his way to the Holy Land — something pivotal to the success of any medieval king. Arguably the most important was his marriage to Berengaria of Navarre in Cyprus, in May 1191. She was the daughter of King Sancho VI of Navarre.


Upon arriving on the coast of Acre, Richard took part in the famous Siege of Acre, recapturing the coastal city for the crusaders. However, he never managed to recapture Jerusalem. Yet this does not mean that this crusade was not a success. The Treaty of Jaffa (which Richard signed with Saladin on the 2nd of September 1192) ensured that Christians would be granted safe access to Jerusalem, and granted all territory between Jaffa and Tyre. They may not have captured Jerusalem, but they captured huge amounts of important territory.


Richard was later captured by Henry VI, the Holy Roman Emperor, on his way back from the Holy Land and imprisoned in Trifels Castle in Germany between December 1192 and February 1194. Fortunately, in his absence, Richard had promoted Hubert Walter (a royal advisor) to Archbishop of Canterbury, and he ran England smoothly, even quashing a rebellion from Richard’s younger brother, John. Walter also managed to raise 100,000 marks — enough to pay Richard’s ransom.


king john illustration
King John of England, via Britannica


Richard returned to England in March 1194 and forgave John for his rebellions. However, he did not stick around and was back on the Continent by June of the same year. Unfortunately for Richard, just five years later, he was shot by an arrow in France, the wound became gangrenous, and he died on the 6th of April 1199.


Richard’s legacy as a king is certainly one of a crusader, rather than an English king. He may have been king of England, but that was in name only; he only spent 6 months of his 10 year reign in England. Richard definitely deserves a place on this list as he achieved far more in warfare and territory terms than many of his predecessors who are also regarded as good kings did, such as William I (r. 1066-88) and Henry II (r. 1154-89). Moreover, Richard’s reign was a period of relative peace with Scotland, something many of his successors failed to achieve.


2. The Saintly Ruler: Louis IX of France (1226-70)

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Saint Louis, artist unknown, c. 13th century, accessed via The Morgan Library & Museum


Louis IX of France is the only king on this list who was canonized. He was canonized by Pope Boniface VIII in 1297, and was the only French monarch to become a saint. He is often regarded as the ideal Christian monarch.


Born on the 25th of April, 1214 near Paris, Louis was the son of King Louis VIII of France (also known as Louis the Lion) and his wife, Blanche of Castile (who was a daughter of King Alfonso VIII of Castile). Louis was only two years old when his grandfather, Philip II, died, and only 12 when his father died. He was crowned that same year, and it is thought that his deeply religious nature came from his mother, who, while ruling in his minority, was reported to have told him:

“I would rather see you dead at my feet than that you should ever commit a mortal sin.”


It is thought that Louis started ruling in his own right by about 1234, which was when he married Margaret of Provence. It was also at this time that Louis’ mother became jealous, and tried to keep the couple apart as much as possible. However, this was not very successful as the couple reportedly had a happy marriage, producing 11 children together.


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The Death of Saint Louis, by Jean Fouquet, Grandes Chroniques de France, c. 1455-60, via


The main feature of Louis’ reign was that he was heavily involved in crusading, going on two separate crusades: the Seventh Crusade in 1248 and the Eighth Crusade in 1270. The former was a disaster for the crusading movement. Arriving in Egypt in early June 1249, the crusaders began their campaign with the capture of the port of Damietta. Unfortunately, the Ayyubid Sultanate knew the territory much better than the crusaders, and the seasonal rising of the Nile River and scorching hot summer temperatures made it impossible for the crusaders to advance. However, on 8 February 1250, Louis lost the Battle of Al Mansurah, where he was captured by the Egyptians.


His release was negotiated, and he spent the following four years in the Kingdom of Jerusalem. It was during this period that Louis used his wealth to help rebuild the crusader states which had been damaged by previous crusading ventures. In addition, he also conducted diplomatic missions with Islamic representatives. He returned to France in the spring of 1254. Throughout the late 1240s and 1250s, Louis was in contact with the Mongol Khans, including Güyük Khan, a grandson of the legendary Mongol leader, Genghis Khan.


On the 24th of March 1267, at a parliament held in Paris, Louis and his three sons took the cross to set out on the Eighth Crusade. The crusaders arrived at Carthage on the 17th of July 1270 but disease had already broken out in the camp. Louis himself died of dysentery on the 25th of August 1270.


Saint Louis certainly deserves a place on this list: he was the only French king to be canonized, and his pious nature did not stop him from going on a crusade. It is also important to note that success in warfare does not necessarily denote a successful medieval king — Louis was the epitome of a Christian medieval king.


3. Hero of the Scots: Robert I of Scotland (1306-29)

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Bust of Robert the Bruce statue, via


You may be forgiven for thinking you have not heard of Robert I of Scotland, but that is because he is much better known as Robert the Bruce. Robert’s claim to the throne came from the fact he was the fourth great-grandson of King David I of Scotland (r. 1124-53), and his claim came about during the period of Scottish history known as “the Great Cause” — when Margaret, the Maid of Norway, had died aged just 6 in 1290 and there was no direct heir to the Scottish throne.


Bruce had been heavily involved in the First War of Scottish Independence against England, which had been raging on since the English invasion of Scotland in 1296. Initially, the war had been fought with William Wallace (known as Braveheart) until his capture and eventual execution by King Edward I of England (who was known as the “Hammer of the Scots”).


After submitting to Edward I in 1302, Robert Bruce inherited his family’s claim to the throne upon his father’s death, but moved quickly and seized the throne for himself in 1306. He was shortly after defeated by Edward I’s forces at the Battle of Methven in 1306, and was forced to go into hiding. However, this did not last for long. Edward I died a year later and was succeeded by his militarily incompetent son, Edward II. Bruce re-emerged from hiding and soundly defeated English forces at the Battle of Loudoun Hill on the 10th of May 1307. This was just the beginning of Bruce’s victories against the English.


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Portrait of Edward I of England in Westminster Abbey, c. 1272-1307, via Historic Royal Palaces


However, it was not until 1314 that Bruce really established himself as a true Scottish national hero, and one of the greatest medieval kings of all time. Facing a far numerically superior English force at Bannockburn on 24 June 1314 (Bruce’s force of approximately 6000 soldiers was up against Edward II’s army of 20,000), something had to go in his favor. The Scottish forces successfully forced the English army back into the Bannock stream, where many of them drowned in their heavy armor. The result was a disaster for Edward II, but a huge morale boost for Scottish forces and Bruce.


In 1320, the Declaration of Arbroath was submitted to Pope John XXII, which acknowledged Robert as King Robert I of Scotland, king of an independent kingdom. Two years later, Bruce raided England again and defeated English forces at the Battle of Byland Abbey. This was a turning point in Scottish warfare, as they had formally surpassed the English with their military techniques; they had ditched the traditional warhorse for more footsoldiers, resulting in a quicker and more efficient victory.


By 1324, Pope John XXII had acknowledged Robert as king of Scotland, and Scotland as an independent kingdom. Edward II died a broken man in 1327 after being deposed in favor of his son, Edward III. The new king recognized Robert’s independence, and concluded it in the Treaty of Edinburgh-Northampton in 1328, by renouncing all claims over Scotland.


Robert the Bruce died the following year, to be succeeded by his son, King David II. Not only is Robert I recognized as one of Scotland’s greatest medieval kings (or greatest king, in fact), but he is generally recognized as one of the greatest medieval kings of all time. To this day, he is still regarded as a Scottish national hero and has been portrayed in numerous books, films, and stage adaptations, most recently in the 2018 film, Outlaw King.


4. Military Mastermind: Edward III of England (1327-77)

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Edward III, artist unknown, c. 16th century, via the National Portrait Gallery, London


Although only briefly part of Robert the Bruce’s reign, King Edward III really came into his own from the 1330s onwards. Born to Edward II and Isabella on the 13th of November 1312, Edward grew up under the protection of his mother and her lover, Roger Mortimer. Upon Edward II’s deposition, Isabella and Mortimer had seized power for themselves, and Mortimer clearly saw the teenage Edward as a threat to what he deemed his rightful seat. However, by 1330, Edward and a band of trusted companions snuck into Nottingham Castle via an underground tunnel on the night of the 19th of October, surprising Mortimer and having him arrested. He was then executed, and Isabella was sent to live in relative comfort but essentially under house arrest for the rest of her life. Edward III was finally ruling in his own right.


Like his father, Scotland greatly concerned him. However, with the young David II sitting on the throne after the death of Robert the Bruce in 1329, Edward had the upper hand. He defeated David’s forces at the Battle of Dupplin Moor (11 August 1332) and then at Halidon Hill (19 July 1333), thanks to the introduction of the longbow into English warfare. Before the majority of the Scottish army had even reached the English forces, they had been slaughtered thanks to the archers with longbows.


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The Battle of Sluys, from the Chroniques de Jean Froissart, 15th century, via the


The longbow would also play an important role in the Hundred Years’ War against France, Edward having already calmed the Scottish threat from the north. One of the biggest battles of the Hundred Years’ War was a naval battle at Sluys, fought on the 24th of June 1340. Edward’s navy outmanoeuvred French forces, capturing all but 23 of the 213 French ships. In addition, all the admirals of King Philip VI (of France) had been either captured or killed.


By 1346 however, Edward had war on two fronts — yet he managed to come out victorious on both occasions. At Neville’s Cross near Durham, England, David II had sent a force down from Scotland, but they were defeated, and David was captured. He would remain in English custody for the next eleven years. Meanwhile, at Crécy in France, the longbows showed their superiority once more; the English were outnumbered by 8 to 1 yet still won the battle.


But it was not just French and Scottish aggression that Edward III had to deal with: his reign saw the arrival of the Black Death in 1347. Edward did not close English borders, as this would have meant closing down trade for England. Nevertheless, he did introduce some legislative measures: the unpopular Statue of Labourers (1351) which put peasant wages back to pre-plague levels (a catalyst for what was to become the Peasants’ Revolt in 1381).


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The Battle of Poitiers, from Chroniques de Jean Froissart, 15th century, via Berkhamstead Castle


By the time the biggest wave of the Black Death had been and gone by the early 1350s, Edward once again focussed his attention on France at the Battle of Poitiers (19 September 1356) one of the finest military victories in English history. He cemented his place as one of the greatest medieval kings although it was largely his son, the Black Prince, who won the battle.


During the battle, the French king, John II, was captured and sent to England and Edward began to slow down throughout the 1360s and 1370s. His son and his eldest grandson had both died by 1376, so Edward’s grandson Richard succeeded him as King Richard II of England when Edward himself died a year later, on the 21st of June 1377.


As well as witnessing numerous military victories against both Scotland and France during his reign, Edward III also saw England through the Black Death, established English as the primary language of England, and cemented England’s position as victorious in the first half of the Hundred Years’ War. To this day, Edward III’s reign is the fifth-longest of any English monarch, coming in at 50 years and 147 days.


5. The Medieval King Who Beat the French: Henry V of England (1413-22)

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King Henry V, c. 16th – 17th century, via the National Portrait Gallery, London


Having a long reign is not necessarily a factor for getting a place on this list. Our final monarch, King Henry V of England, ruled for less than a decade, but achieved notable successes in his short tenure as a medieval king.


Henry was born on the 16th of September 1386 in Monmouth Castle, Wales, the eldest of six children between King Henry IV of England (r. 1399-1413) and his first wife, Mary de Bohun.


When the future Henry IV was exiled by his cousin King Richard II of England (r. 1377-99), the young Henry was taken into Richard’s care, and reportedly treated very well. He even joined Richard in Ireland, and it was while he was in Ireland that news had traveled that Henry’s father had usurped the throne, and been crowned as King Henry IV of England. Upon his coronation, the young Henry was recalled back to England. He was created Prince of Wales and Duke of Lancaster. He also served as High Sheriff of Cornwall at the turn of the fifteenth century.


Henry was involved in the military before he was crowned king, helping to supress Owain Glyndwr’s revolt. However, when his father died, Henry was immediately crowned King Henry V of England. Carrying on the Hundred Years’ War, which had been started by his great-grandfather, Edward III, Henry turned his attention to France. On the 12th of August 1415, he sailed to France, capturing Harfleur on the 22nd of September. Next, despite warnings from his council, he decided to march his army across France to Calais. However, his army was intercepted near the village of Agincourt, which ultimately led to one of the most famous battles in history: The Battle of Agincourt.


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The Battle of Agincourt, by Enguerrand de Monstrelet, 15th century, via


Despite the horrifically muddy conditions, and the exhaustion of the numerically inferior English forces, they decisively beat the French, in one of the greatest underdog stories of all time, in a victory which propelled Henry V’s legacy as one of the greatest medieval kings of all time. Agincourt is typically regarded as Henry’s greatest military victory, and in terms of English victories during the Hundred Years’ War, Agincourt ranks alongside Crécy and Poitiers.


Henry’s reign and victories were only short-lived, though. He had captured enough territory and had enough of a solid claim to crown himself King of France, though he never lived to see it through. Henry died (likely of dysentery) on the 31st of August 1422, aged just 35. He named his brother, John, Duke of Bedford, as regent of France in the name of his son, who would become the future King Henry VI of England, as he was only a few weeks old at the time.


Winning such significant victories in the Hundred Years’ War and solidifying English territory abroad cemented his position on this list. He was also romanticized in many of Shakespeare’s plays, and to this day is still seen as one of the greatest medieval kings of all time.

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By Chester OllivierBA (Hons) HistoryChester is a contributing history writer, with a First Class Honours degree BA (Hons) in History from Northumbria University. He is from the North East of England, and an avid Middlesbrough FC supporter.