Weird History
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Who Was The Toughest Of History’s Legendary Warriors?

Updated September 23, 2021 6.9k votes 1.3k voters 44.8k views16 items

List RulesVote up the warriors who would fare best in a "Battle Royale" situation.

In the era of the battle royale, it’s no wonder that renewed interest has arisen in deciphering once and for all who the toughest warriors of all time were, both in the general sense and in the specific. Ranking various historical armies and their members is all well and good, but the real excitement comes from matching up the most notable military figures from the annals of history and trying to figure out which of them would win in an all-out fight to the finish. 

Back in the days before firepower became the deciding factor in warfare, military leaders could play a more direct role in combat, and some of history’s greatest men and women weren’t afraid to get their swords dirty right alongside their troops. It is these historical brawlers who make for the best hypothetical fight cards and for some truly combative debates. 

  • Photo: Unknown / Wikimedia Commons / Public Domain

    Where and When: As if his nickname weren’t enough indication, Alexander the Great is considered to be one of the very best military leaders in all of history. In just seven short years as King of Macedon from 336 to 323 BCE, Alexander went conquest-wild and earned himself a bunch of other titles like King of Persia, Pharaoh of Egypt, and Lord of Asia. In anticlimactic fashion, however, he perished on his way home by either natural causes or poison.

    The Arsenal: Alexander’s father, Philip II, refurbished the Macedonian army before handing it off to his son. Under his reign, infantry started to carry an enormous sarissa, a 22-foot pike with an iron tip that could be used to take down charging cavalry with ease. Alexander is alternately depicted wielding either a spear on horseback or a much shorter sword, but he’s always shown in shining armor. 

    His Training: Of all the legendary leaders of antiquity, Alexander the Great probably had the best education. He was personally tutored by Aristotle throughout his youth in everything but the art of warfare, which he learned directly from his father. While much of the focus would have been on strategy, it’s also obvious that Alexander was brought up to be an excellent fighter.

    In The Duel: The most famous swing of Alexander’s sword was at an inanimate object, the Gordian Knot, but that doesn’t mean he wasn’t capable on the battlefield. In combat against the Persian Empire, he led his Royal Companion Cavalry charging right into the heart of the enemy. In one particular incident, Alexander was said to have caught up to Darius’ fleeing chariot and dispatched the driver, only for Darius to escape his clutches. If Alexander is showing up at a fight, he’s doing so on horseback, and with a brilliant strategy already in mind to defeat his opponent.

    • Age: Dec. at 33 (355 BC-322 BC)
    • Birthplace: Pella, Greece
  • Photo: ItwasntSuperman / Wikimedia Commons / CC BY-SA 4.0

    Where and When: Saladin was one of the greatest heroes during the Crusades era, thanks to some rather impressive victories on his resume. Ruling over modern Egypt, Syria, Yemen, and Palestine from 1169 until his passing in 1193, Ṣalāḥ al-Dīn Yūsuf ibn Ayyūb won renown for capturing Jerusalem from the Franks and from fighting Richard the Lion-Heart to a difficult draw in the Third Crusade.

    The Arsenal: Saladin was known to wield a large scimitar in battle, and he wasn’t afraid to use it. On one occasion, he is said to have personally cut the head off a notorious French crusader. Anything else is secondary when one has a big sword in their hands and is willing to swing it head-high.

    His Training: From a young age, Saladin took mentorship from brilliant military minds, including the famous anti-crusader Nur al-Din and Shirkuh, his uncle. They would have personally trained him in both combat and strategy, lessons that he carried with him in his own rise to prominence.

    In The Duel: Saladin could be brutal when necessary and engaged in his fair share of executions, but he was also wise enough to avoid violence for violence’s sake. One of his battlefield trademarks was his remarkable willingness to put himself at risk, charging into battle without any care for his own life, but that could either pay off or backfire horribly in a duel with other, perhaps more cautious, historical figures. 

    • Birthplace: Tikrit, Iraq
  • Photo: Jacques-Louis David / Wikimedia Commons / Public Domain

    Where and When: Well-known by most as the central figure of the Battle of Thermopylae in 480 BCE (of 300 fame,) King Leonidas of Sparta led his city-state through a bloody 10-year reign. His primary mission in life was to halt the Persian invasion of Ancient Greece, which he ultimately did, though he gave up his life to do it.

    The Arsenal: As part of a Spartan phalanx, Leonidas had no need for his own special set of equipment. In fact, it would have been counterproductive if he did. Spartan strategy revolved around every warrior having the same set of round shield, long spear, and short sword, which they then employed in a tight formation to overwhelm their enemies. Armor was secondary, though it certainly wasn’t as sparse as it appears in Hollywood adaptations. 

    His Training: Leonidas’ older half-brother was the heir to the throne of Sparta, and so young Leonidas entered into Hoplite training like any other Spartan commoner would have. This meant that the military culture of Sparta was fully ingrained in him and that he learned how to command a phalanx, the tactical trademark of the city-state.

    In The Duel: King Leonidas might be in some trouble when it comes to a series of duels with other historical figures. Though he was undoubtedly a powerful fighter, he was used to working as part of a phalanx, and thus relied entirely on the support and positioning of his comrades to be effective in battle. If one takes a Spartan out of the phalanx, it should dramatically reduce their effectiveness, making Leonidas just another tough guy in a field that’s crawling with them. 

    • Age: Dec. at 60 (539 BC-479 BC)
    • Birthplace: Sparta, Greece
  • Photo: Anonymous / Wikimedia Commons / Public Domain

    Where and When: If Vlad the Impaler isn’t a household historical name, then the fictional character that he inspired certainly is: Dracula, Lord of the Vampires. Vlad III wasn’t an undead monster, but he was the rather bloodthirsty ruler of Wallachia throughout a tumultuous 15th century. He led Wallachia on three separate occasions, with his last stint ending in his death in battle - and, yes, along the way he did impale his fair share of enemies. 

    The Arsenal: Vlad III was a big fan of skewering his opponents on spikes as a show of brutality, but that wasn’t his go-to weapon on the battleground. Having been trained while a captive of the Ottoman Empire, Vlad became very familiar with the traditional weapons of the janissary including the bow, the javelin, and a curved scimitar. 

    His Training: Vlad spent much of his childhood as a hostage of the Ottoman Empire, which included plenty of torture, but they also trained the young man in the art of warfare. Learning alongside future janissaries, Vlad benefitted from their legendary martial discipline and vicious tactics, and he did it all without ever actually becoming loyal to the Empire itself. 

    In The Duel: Legend tells that Vlad the Impaler earned his second stint on the throne of Wallachia by personally beheading his predecessor, Vladislav II, in combat. That, combined with the whole impalement thing, gives a pretty good idea of what to expect from Vlad in any duel: brutality, viciousness, and unfettered violence. He might not be the most skilled swordsman in the fight, but he’s probably the meanest. 

    • Birthplace: Sighișoara, Romania