Charlemagne
[ranking: 13]
Royal Title: Charles the Great, Holy Roman Emperor, King of the Franks Most Brutal Moment: Charlemagne was constantly at war, but his most brutal moment came at the Massacre of Verden in 782. The Royal Frankish Annals record Charles slaughtering 4,500 pagan Saxons after their nobles refused to hand over their war leader, Widukind. Charlemagne's forces, including some of his best men, had previously lost the Battle of Süntel to Widukind and his men. As the story goes, Charlemagne retaliated by killing thousands of Saxon men, all in one day. It's worth noting that Widukind escaped, though he surrendered and converted to Christianity three years later.
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John of England
[ranking: 10]
Royal Title: John, King of England Most Brutal Moment: Shall we count the ways? The youngest son of the famously energetic King Henry II and his Crusading, duchy-ruling bride, Eleanor of Aquitaine, John lived up to neither of his parents' legacies. Although the English did get the Magna Carta from him, John wasn't a fan of his subjects: He locked 22 knights in a castle and starved them to death. John also betrayed his older brother, King Richard the Lionheart, who was on a Crusade, by rebelling against him. John may also have arranged the murder of his nephew Arthur of Brittany. Finally, he made an enemy of one of his French vassals by stealing the man's bride-to-be!
Galeazzo Maria Sforza
[ranking: 2]
Royal Title: Galeazzo Maria Sforza, Duke of Milan Most Brutal Moment: A master torturer and true evil mastermind, Galeazzo Maria once chopped off a rival's hands and killed a poacher by making him swallow an entire hare. This fifteenth-century duke of Milan came by his brutal personality honestly. The surname of his warlord-turned-noble family, Sforza, means "force" in Italian. One contemporary writer recorded how Galeazzo Maria, upon asking a priest how long he would reign in Milan and being told only eleven years, stuck the good father in jail with just a little bit of food. As the story goes, "the man survived on these things, even getting to eat his own excrement, for twelve days. Then he died." Galeazzo Maria was also accused of organizing gang rapes and of poisoning his own mother.
William the Conqueror
[ranking: 15]
Royal Title: William I, King of England, Duke of Normandy Most Brutal Moment: A fierce warrior and the first Norman king of England, William the Conqueror made his name by taking Albion at the Battle of Hastings in 1066. But he had quite the reputation already as duke of Normandy in France... and as an abuser. When William sought the hand of a particularly high-born woman, named Mathilda, she rebuffed him, saying she was too good for a bastard; legend has it that he dragged her around by her hair until she agreed to marry him. As the illegitimate son and young heir of Duke Robert I, William faced assassination attempts and coups from an early age, but he turned that into motivation to consolidate his own power. William crushed multiple rebellions in Normandy, then turned to England. Perhaps as many as 10,000 men, both Saxon and Norman, died at the Battle of Hastings, and William kept a tight grip on his conquests from then on.
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Ferdinand I of Naples
[ranking: 5]
Royal Title: Ferdinand I, King of Naples Most Brutal Moment: Killing his rivals and building a "museum of mummies" with them in his palace. Born the illegitimate son of a Spanish monarch, Ferdinand enjoyed keeping his deceased enemies around. Once, he invited some French "pals" (a.k.a. agents of his rival to the throne of Naples) to dinner. After they ate, he then imprisoned others for thirty years, even shoving one guy out a window to his death. Some were propped up in a mock banquet at Castel Nuovo; the bodies were pickled and turned into mummies, then re-dressed to look lively.
Robert II of France
[ranking: 12]
Royal Title: Robert II, King of France (a.k.a. the Franks) Most Brutal Moment: Perhaps the first monarch to burn heretics, Robert II was called "the Pious," but he might as well have been dubbed "the Brutal." In 1022, Robert ordered several individuals burned alive in the city of Orléans. These "heretics," hunted out by an undercover spy, supposedly belonged to an orgy-obsessed cult that worshipped demons and killed babies. Robert naturally had them burned alive.
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