Chivalry was a moving target, shaped by war, religion, and court life, and it changed depending on who was defining it: clerics advocating restraint, nobles protecting their status, and warriors who preferred customs that made it more worthwhile to take prisoners than to kill them. Medieval chronicles and later biographies portrayed certain knights as pure and luminous symbols, and these accounts continue to shape our image of armor and honor. At the same time, historical records are rife with raids, broken truces, and brutal politics—often carried out by the very social class that most strongly championed virtue. Here are ten knights whose lives helped define chivalry, and ten infamous figures who demonstrate just how easily this code could be circumvented—or even ignored.
1. Guillaume Marshal
William Marshal rose from being a younger son with limited prospects to becoming one of England’s most respected knights, and his career was celebrated in a nearly contemporary biography, The History of William Marshal. He made a name for himself through his loyalty across multiple reigns and later served as regent for Henry III—not the kind of role entrusted to someone considered reckless or self-serving.
2. Geoffroi de Charny
Geoffroi de Charny is significant because he did more than just fight; he attempted to define in writing, in The Book of Chivalry, what an honorable battle should be. He died at the Battle of Poitiers in 1356 while defending the French royal banner, which was in keeping with the ideal he championed: remaining calm under pressure and taking one’s duty seriously.
3. Sir John Chandos
Chandos was a prominent English commander during the Hundred Years’ War and one of the founding members of the Order of the Garter, an organization created to reward a certain ideal of conduct among the elite. Chroniclers praised his discipline and judgment, and this reputation was important at a time when undisciplined troops could ruin a campaign just as easily as an enemy army.
4. Bertrand Du Guesclin
Du Guesclin became Constable of France, and his rise reminds us that chivalry was not merely about elegance and pomp. He earned respect through his perseverance, his practical leadership, and his unwavering loyalty in long and grueling conflicts where glory was rare and endurance mattered most.
5. Sir James Douglas
Known in Scottish tradition as “Good Sir James,” Douglas linked his name to the cause of Robert Bruce, and the bond between them became an integral part of Scottish national history. The accounts claiming that Douglas took Bruce’s heart with him on a crusade and died in Spain in 1330 reflect a medieval ideal of service that outlived the person he served.
6. Jean Le Meingre, also known as Boucicaut
Boucicaut left behind a reputation shaped by a detailed biography that portrayed him as a model knight, emphasizing discipline and public conduct. He advocated a version of chivalry that included restraint and the protection of the most vulnerable, even though the politics of the time constantly tested the limits of these principles.
7. Bayard
Pierre Terrail, Lord of Bayard, became a symbol of chivalric virtue during the Renaissance, praised for his courage and integrity at a time when alliances were constantly shifting. Accounts of his courtesy and concern for civilians may have been embellished by his admirers, but the fact that his name became a benchmark speaks volumes about what people expected from the chivalric ideal.
8. Balian of Ibelin
Balian is remembered for defending Jerusalem in 1187 and negotiating the terms of surrender that spared many civilians after the city could no longer hold out. This episode, recounted in numerous accounts from the time, illustrates a practical form of chivalry: a sense of responsibility for human life, and not just personal courage.
9. Maximilian I
Maximilian I cultivated the image of a chivalrous ruler through tournaments, suits of armor, and commissioned works such as Theuerdank, transforming the chivalric ideal into a political and cultural project. He played an important role because chivalry was also a brand, and he knew how to use it to shape the public’s perception of power.
10. Sir Philip Sidney
Sidney’s chivalry was part of a later, more literary version of chivalry, but his reputation still rested as much on his conduct as on his talent. The story that he gave water to a wounded soldier at Zutphen in 1586 has endured because it portrayed honor as generosity in the face of adversity, and not merely as courage in battle.
Here are ten knights who treated this code as optional and left behind a legacy that tarnishes the very idea of chivalry.
1. Gilles De Rais
Gilles de Rais fought alongside Joan of Arc and held a high rank as Marshal of France, which makes his subsequent downfall all the more chilling. He was tried and executed in 1440 after being found guilty of the murder of children—a case preserved in the judicial archives that is a world away from the romantic image of chivalry.
2. Hugh Despenser the Younger
Despenser was a favorite at the court of Edward II and used his proximity to power to enrich himself and exert control through intimidation. Contemporary accusations portrayed him as a predator, and his career became a cautionary tale of how the language of noble duty could be associated with personal greed.
3. John Tiptoft, Earl of Worcester
Tiptoft had a reputation for being learned, but he became infamous during the War of the Roses for his harsh judgments and mass executions while serving as Constable of England. He is remembered as a ruthless man, even by the standards of that violent era, which shows just how easily the role of a knight could be exploited to legitimize cruelty.
4. Sir Andrew Harclay
Harclay earned his reputation by fighting the Scots, but then suffered a sudden downfall when he negotiated peace with Robert Bruce without the king’s consent. He was arrested and executed for treason in 1323, and the speed of his downfall shows just how often loyalty—rather than bravery—determined whether a knight was praised or destroyed.
5. Sir John Oldcastle
Oldcastle began as a respected soldier and associate of Henry V, but later identified with the Lollard movement and openly defied the authority of the Church. He was convicted of heresy and subsequently executed, a reminder that chivalry was tied to institutional loyalty, not merely to personal ethics.
6. Sir John Hawkwood
Hawkwood made a name for himself as a mercenary captain in Italy with the White Company, serving the city-states that hired him and striking fear into those that could not. His career revealed the commercial side of chivalry, where contracts and pay could matter more than oaths, and where civilians often bore the brunt of it.
7. Sir Robert Knolles
Knolles became wealthy and influential as a result of the war in France, but his name also appears in critiques of the undisciplined raids and the damage caused by those campaigns. The chivalric image depended on control and restraint, and commanders who could not keep their forces in check undermined the very ideals they claimed to represent.
8. Sir John Fastolf
Fastolf’s legacy is ambiguous, for while he was a capable soldier and administrator, his name became associated with cowardice after the Battle of Patay, and he spent years defending his reputation. This episode illustrates how chivalry could be as much a matter of public discourse as of conduct, with reputations made or broken by rivals and chroniclers.
9. Götz von Berlichingen
Götz was an imperial knight in a Germany where private feuds still functioned as a form of politics, and his career was marked by raids and violent disputes that later readers romanticized. His life reflects the dark side of chivalry, where local power could mean carrying out personal vendettas with armed men.
10. Reynald de Châtillon
Reynald became known throughout the Crusader states for his aggressive raids and breaches of truces, particularly attacks that threatened trade routes and pilgrims. Both Muslim and Christian sources describe him as dangerously provocative, and his death at the hands of Saladin after the Battle of Hattin in 1187 served as a clear warning against arrogance masquerading as bravery.