Frenemy Kings: Richard the Lionheart and Philip Augustus

We travel to late 12th century Europe and meet two kings who started as allies and ended as bitter enemies.  Their rivalry changed Western European history.

Transcript

Frenemy Kings: Richard the Lionheart and Philip Augustus

March 2026

“We, however, place the love of God and His honor above our own and above the acquisition of many regions.”

Richard I of England

And from Richard but it is probably apocryphal 

“I would have sold London if I could have found a buyer.”

“Amico et fideli suo ac fratri” (My friend, faithful, and brother).

Philip II of France, referring to Richard. 

When did we stop using epithets to describe rulers?  Even the vaunted AI-driven search engines are not sure.  One said that, kinda, sorta, the last was Alphonso XIII of Spain, or El Africano, for his Africanist views.  Many modern rulers have sported them.  We have two “greats” in Russian history since the 18th century and another in Prussia.  We have tagged some American presidents, with Lincoln as the Great Emancipator and Ronald Reagan as the Great Communicator.  But these were bestowed more by the press looking for a hook than by historians, contemporaries, or writers trying to differentiate between rulers who happened to have the same name. And where we have Charlemagne or Charles the Great, there is no Ronald Magnus Communicare.  

The Middle Ages were different. 

Part of the reason was obviously a ruler, his nobles – especially the one benefiting from his rule, his subjects, or historians of the time wished to impart a bit of flair to the name.  Epithets were also a practical tool for identification in an era before standardized surnames, and as a form of political propaganda to solidify their legacy.

In a world where royal naming pools were extremely small (think of how many kings named “Louis,” “Edward,” or “Henry” existed), these nicknames were essential for distinguishing one ruler from another in historical records and legal documents.  Therefore, I find it rather odd that a great Angevin King such as Henry II, who died in 1189, did not have an epithet, given that there were several other Henrys, even other Henry IIs.  You have a Henry II, Holy Roman Emperor, who died in 1024.  A Henry II of France in the modern period, and even a few other Henry IIs, such as the Duke of Bavaria from the 10th century.  Yet our Angevin Henry, founder of the Plantagenet Dynasty, grantor of an incredible judicial system to England, and the most powerful monarch of 12th-century Europe, did not receive a special name.  

Not all of these names were positive, of course.  You had Ethelred the Unready, Charles the Simple, and another Charles – the Fat.  Ouch. William of Sicily was bad, but worse was Pedro of Castile, the cruel.  And in the 15th century, France, to its detriment, had Charles the Mad.  

Henry II of England may not have gotten a cool nickname, but his son, Richard (1157–1199), arguably got the best: the Lionheart.  How vibrant, compelling, and enthralling is that name. There was a Lion, a title held by another contemporary of Henry II, also, shockingly, called Henry, who was the Duke of Saxony.  But the Lionheart sounds so much cooler.  When rendered into French, which Richard would have spoken as his first language, it sounds even better, Richard, Coeur de Lion. 

And Richard’s contemporary and great rival, Philip II of France (1165 – 1223), received the title of Augustus, hearkening back to the foundation of the Roman Empire.  And one of the epic stories of both medieval France and England was the rivalry between these two exquisitely named individuals.  

The rivalry between Richard I of England and Philip II of France was one of the defining political and military contests of the late twelfth century. Their relationship, forged across two continents, combined friendship, cooperation, suspicion, and, later, open warfare and great enmity, which shaped the political landscape of medieval Western Europe. 

Both men were powerful rulers who expanded royal authority in their respective kingdoms, but they pursued very different strategies and goals. Their conflict unfolded across multiple stages: early alliance, joint participation in the Third Crusade, and ultimately bitter rivalry over lands in France that belonged to the English crown.

Richard I of England was born in 1157, the third legitimate son of Henry II of England and Eleanor of Aquitaine. Later, after the deaths of his older brothers, William and Henry, Richard stood in line of succession as heir to the crown.

As a member of the powerful Angevin dynasty, Richard inherited a vast network of territories that stretched across England and much of western France, including Aquitaine, Anjou, Normandy, and other lands collectively known as the Angevin Empire.  One bit of historiography here.  We call it the Angevin Empire, a derivation from Anjou, the house from which Henry II originally came; his father, Geoffrey, was count of Anjou.  Henry II was not a direct descendant of English kings but rather was named so through his mother, Matilda, daughter of Henry I and granddaughter of William the Conqueror.  

A little digression regarding the English dynasty in Power from 1156 – 1399 or even 1485, depending on who counts a family member.  “Plantagenet” originates from the Old French nickname Plante genest (or Plantegenest), meaning “sprig of broom”. It refers to the common yellow-flowering broom shrub (planta genista) found in western France. The name stems from a personal emblem worn by Geoffrey, and thus, when we refer to Henry as Angevin or Plantagenet, it is really the same family.  We will continue to refer to the Angevin Empire, but from this point on, the family will be known as the Plantagenets. 

Richard spent much of his youth in Aquitaine, his mother’s original domain, where he developed a reputation as a skilled warrior and capable military commander. Known for his courage and aggressive leadership, he also cultivated the image of a chivalric knight, gaining admiration among contemporaries. It was this intentional cultivation of martial skills that laid the foundation for what would later become his epithet.  

Philip II of France was born in 1165 and became king of France in 1180. Unlike Richard, whose lands were scattered across Europe, Philip ruled a kingdom that was still consolidating power. The French monarchy had long struggled to assert authority over powerful feudal lords. When Philip took the throne, the English king technically controlled more territory in France than the French king himself. Philip therefore pursued a strategic policy aimed at weakening the Plantagenet rulers and strengthening the Capetian monarchy. And whereas Richard’s father strode across Western Europe like a titan, Phillip’s father, Louis VII (also no epithet), was seen as weak and unmartial.  It did not help matters that Louis’ first wife, Eleanor, heiress of Aquitaine, would divorce Louis and marry none other than his great rival, Henry II.  Nor that at the time of their marriage, Henry was 19 when Eleanor was 30, and that this wedding occurred just 8 weeks after her annulment from Louis.  I realize that the movie Lion in Winter is historical fiction. However, it is hard not to pepper in some of the quotes, such as when married Eleanor describes meeting Henry, “He came down from the North to Paris with a mind like Aristotle’s and a form like mortal sin. We shattered the Commandments on the spot.”

During Richard’s youth, both he and Philip had reasons to cooperate. The political situation in Western Europe was fluid, and alliances often shifted quickly. Richard and Philip initially became allies against Henry, who had a hard time keeping his tempestuous sons, Richard, Geoffrey, and John, and even the initial heir before his death, the young Henry, under wraps.  And it did not help that their mother, Eleanor, had been set aside by Henry in favor of a series of mistresses.  In fact, after one of the revolts involved Eleanor herself, Henry locked his wife in a castle.  Though Richard and Phillip’s alliance helped pressure Henry, it was not until his death that Richard could come into his full inheritance.

Shortly after Richard became king, news reached Europe of the fall of Jerusalem to Turkish Muslim forces under Saladin in 1187. The loss of the city shocked Christian Europe and led to the launching of the Third Crusade. Both Richard and Philip took the cross and agreed to lead major expeditions to the Holy Land.  The first crusade was led by senior noblemen, not the actual kings.  The Second Crusade changed that, featuring not only Louis VII (with Eleanor along for the expedition), but also Conrad, the Holy Roman Emperor.  Yet the 2nd Crusade, which targeted the major city of Damascus, ultimately failed, creating an opening for the Turks. Saladin won a decisive battle over the Franks at Hattin in 1187, which led to the reconquest of Jerusalem, which had been in Christian hands for 80 years.  So when Jerusalem fell, it was considered the pious move to go to the Holy Land.  

Originally, a third figure, Frederick I, Holy Roman Emperor, with yet another cool name, Barbarossa, or red beard, was to go with him, but he died on route.  His death, which might have tempered the two younger rulers, was a blow on many levels.  

The two kings traveled separately but eventually met in the eastern Mediterranean. One of the first major operations of the crusade was the siege of Acre. The siege lasted nearly two years and was one of the most significant military campaigns of the crusade. Richard’s arrival with reinforcements helped turn the tide, and the city eventually fell to the Crusaders in 1191.

Despite this success, tensions between Richard and Philip soon became evident. Their rivalry stemmed partly from personal competition and partly from broader political concerns. Philip, watching Richard add to his martial reputation, worried that Richard’s military successes would increase the prestige and influence of the Plantagenet dynasty. Richard, meanwhile, believed Philip was more interested in weakening England’s position in France than in prosecuting the crusade. It also did not help that Richard, once dependent on Phillip’s help during his revolts against his father, was now the far more powerful of the two men, as Assistant Professor of History at Christendom College, Brendan McGuire notes, “Richard also towered over Philip in personal charisma, charm, and popularity.  He appeared to his contemporaries to be the very incarnation of the knights of poetry: in the prime of young adulthood, handsome, strong, fearless, outgoing, and deeply devoted to the crusading cause.  Philip, on the other hand, was neither a robust man nor a popular one among his vassals, and the harsh climes of Syria and Palestine would prove to be too much for him.”

After the fall of Acre, Philip decided to return to France, citing illness and political necessity. Before leaving, he promised not to attack Richard’s lands during his absence. Uh huh. 

As Simon Rees notes, ‘In tackling Richard’s power base, Philip was treading a fine line. Richard was still on crusade, and the rules were very clear: A Crusader’s lands were protected by the church, and they could not be attacked while he was still away. That, of course, did not stop Philip from making the necessary moves to retrieve dowry lands and more if possible.”

As it turned out, soon after his return, Philip began maneuvering diplomatically and militarily to take advantage of Richard’s prolonged stay in the Holy Land.

Richard remained in the eastern Mediterranean for much longer and became the crusade’s central military leader. His victories, particularly at the Battle of Arsuf in 1191, enhanced his reputation as one of the greatest commanders of his era. Nevertheless, despite his battlefield successes, Richard ultimately failed to recapture Jerusalem. By 1192, he negotiated a truce with Saladin that allowed Christian pilgrims access to the city but left it under Muslim control.

But with Richard away, the Capetian king forged alliances, including with Richard’s younger brother, John, which was a neat little turnabout given that Richard had caused headaches for his father, and now his brother did the same with another English King. John hoped to gain power in England while Richard remained abroad. And why not?  Richard had revolted against his father, so why not a brother?  It was the Plantagenet way.  

Philip also launched military campaigns to seize strategic territories, including Normandy. These lands were vital components of the Angevin Empire and central to English influence in continental Europe. Normandy was also the original French duchy that William the Conqueror had ruled prior to taking the English throne.  It has been joined with England since 1066. By challenging English control in these areas, Philip sought to shift the balance of power permanently in favor of the French monarchy.

Richard’s return journey from the crusade proved disastrous. In 1192, he was captured by Leopold V, Duke of Austria, and eventually handed over to Henry VI, Holy Roman Emperor. Richard remained imprisoned for more than a year while an enormous ransom was raised for his release.  The ransom demanded by Henry VI in 1194 was 150,000 silver marks (around 100,000 pounds of silver), which is approximately $3.3 billion in modern purchasing power. This colossal sum equaled nearly three years of income for the English Crown.  And it was all illegal, as neither Leopold nor Henry VI had the right to detain a Crusader.  Yet Leopold and Henry had a personal beef. During the Third Crusade at the Siege of Acre (1191), Richard I ordered the Duke’s banner to be cast down from the walls, a profound insult to Leopold and the Holy Roman Empire.  Leopold also suspected Richard of arranging the assassination of his cousin, Conrad of Montferrat, in Jerusalem.

During this period, Philip and John both attempted to prevent Richard’s return. Philip reportedly sent messages urging the emperor to keep Richard imprisoned longer, recognizing that Richard’s absence weakened the Angevin position.

Richard was finally released in 1194 after the massive ransom was paid. He returned to England briefly but quickly shifted his attention to France, where Philip had been expanding his influence.

From 1194 until Richard died in 1199, the two kings fought an intense series of wars across France. Richard proved to be a formidable commander, winning several engagements and regaining lost territory. One of his most famous strategic achievements during this period was the construction of the powerful fortress Château Gaillard, designed to defend Normandy against French attack.

Richard’s military skill allowed him to hold Philip at bay for several years. Despite Philip’s growing administrative and political power, he often struggled to defeat Richard directly on the battlefield. Contemporary chroniclers frequently praised Richard’s tactical brilliance and personal bravery.

However, Richard’s constant warfare placed heavy financial burdens on his kingdom. Maintaining armies and fortifications required vast sums of money, and taxation increased significantly during his reign, not to mention that massive ransom.

Could Richard have perpetuated the Angevin Empire and seen Philip fall?  We will never know.  In 1199, Richard was mortally wounded while besieging a small castle at Châlus-Chabrol Castle. His death dramatically altered the balance of power between England and France.

Richard’s successor, John, lacked his brother’s military ability and political authority. Philip quickly took advantage of this weakness. Over the next decade, Philip captured large portions of the Angevin territories, including Normandy in 1204. These victories represented a major turning point in European history, as they greatly strengthened the French monarchy and reduced England’s influence on the continent.  By the time Phillip died in 1223, two decades after his rival, only a portion of the once mighty Angevin Empire remained: Gascony. 

The rivalry between Richard I of England and Philip II of France was more than a personal feud. It symbolized a broader struggle between two competing political systems. The Plantagenets controlled a vast but loosely organized empire of territories organized as vassals, while the Capetian kings were steadily building a centralized French state.  Where it got tricky was that in many ways, the Plantagenets owed vassal service to the French King himself. 

Richard became legendary as a warrior king. His exploits during the Third Crusade and his reputation for bravery made him one of the most famous figures of the Middle Ages. The Couer De Lion. Yet he spent little time in England and focused primarily on warfare abroad.

Philip Augustus, in contrast, is often remembered as one of the most effective administrators in medieval French history. Through careful diplomacy, legal reforms, and strategic warfare, he dramatically expanded royal authority and laid the foundations for a powerful French monarchy. What was a rump state under his ancestors became a kingdom capable of challenging the English and the Holy Roman Empire.  

Their conflict reshaped the political map of Europe. By the early thirteenth century, the Capetian dynasty had emerged far stronger than it had been when Philip first took the throne. Meanwhile, England’s continental empire had begun to collapse.

So, who is the better King?  Richard is famous, and his success as a warrior makes him the darling of both contemporary sources and many readers today.  On the other hand, Philip, well, a little bit of a conniver, treacherous, and not nearly as martial.  I have a rather simpler question than who possessed greater fame or character.  Who left their kingdoms better off?  The only real answer to this is Philip.  Upon his death, France was unquestionably more powerful and better positioned.  One has to go back to the Carolingians to find a French ruler who directly controlled more territory or who had better command of unruly nobles.  In his consolidation of power and his wily diplomacy, Philip represents more modern kingship than the thoroughly medieval, chivalric Richard.  A later French King, Louis XI, nicknamed the Spider, had his antecedents in Philip’s time.  

Yet Richard’s failures were not so much his decisions as the fickle hand of fate.  Philip should have stayed in the Holy Land and finished the job as Richard tried to do.  What was the point of going in the first place if not to complete the reconquest of Jerusalem?  Richard should never have been detained in Austria, as that broke Christian, papal-certified law.  And at Richard’s untimely and accidental death, he still had the upper hand.  His death was not like he died in a blaze of glory, charging at Saladin.  A stray bolt hit him.  

But Richard also made many poor decisions.  His bravery was legendary, but knowing that John was his successor, he not only failed in his kingly duty and fathered no son of his own, but his courage did him in, opening the way for John. What was he doing that close to the front line while besieging a minor castle?  After insulting Duke Leopold, perhaps journeying through his lands was not prudent.  And finally, he underestimated Philip.  

McGuire here offers an interesting contrast: Medieval Warrior and Crusader vs. King. 

“In the end, though, it was as a king rather than as a crusader that Philip Augustus outshone Richard the Lionheart.  Despite being an indifferent crusader, Philip had a clear vision of what was necessary for the firm establishment of Capetian sovereignty in France. He pursued this end relentlessly, destroying the independence of fractious vassals, shattering Angevin ambitions with his conquest of Normandy in 1204 and his victory at Bouvines in 1214, and ultimately changing the royal office forever by the time of his death in 1223.  What he had inherited in 1180 was really an ambiguous lordship as “King of the Franks,” little more than a primus inter pares in a land with thousands of independent nobles and ambitious barons, frequent private wars, and no political unity whatsoever.  By the time of his death, he had forged France in the proper sense—indeed, it was with justice that he became the first king to claim the title “King of France.”