Weird History

Which General Would Win In An All-Out War Between History’s Greatest Military Leaders?  

Quinn Armstrong
7k votes 1.2k voters 22.8k views 14 items

List Rules Weighing only the skills of the generals, vote up those who would win an all-out war.

The great military theorist von Clausewitz once wrote "war is the realm of chance." So many unpredictable factors affect success in battles. How can we discuss skill or generalship when a chance of rain the night before a battle might completely change its outcome? And yet, as the greatest generals know, there are no excuses in combat. If it rains, the rain must be accounted for and turned to an advantage. Adaptability, courage, charisma, and intelligence all play a part in a successful military campaign.

The generals in this imaginative exercise are the best of the best. These are the generals who have won the most battles against the greatest odds, who have forged empires, and who have left indelible marks on world history.

So how to decide between them? It's important that only the general's individual skill be considered. Naturally, Erwin Rommel's tanks would demolish the armies of Hannibal Barca, but if the technological gap were ignored, would Hannibal's encirclement technique defeat the Desert Fox? Would Takeda Shingen's lightning cavalry shatter the brilliant defensive tactics of Georgy Zhukov if they had similar numbers and equipment? Vote up the general you think would dominate in an all-out brawl between the most brilliant military minds history has to offer.

Alexander the Great is listed (or ranked) 1 on the list Which General Would Win In An All-Out War Between History’s Greatest Military Leaders?
Photo: Unknown/Wikimedia Commons/Public Domain

Where And When: When Alexander the Great was born, in 356 BCE, he had a huge military head start. His father, Philip II, had assembled a great army. However, without Alexander's military genius, it's unlikely even that mighty army would have gone on to conquer an unprecedented amount of territory, creating one of the largest empires of the ancient world.

Win/Loss Ratio: 100% (9 wins, 0 losses)

His Greatest Achievements: Alexander was a prodigious tactician and a great military innovator. One of his most consistent tactics was to arrange his troops in a signature wedge shape, which made it easier to defend the core of the army from archers, and allowed cavalry to sweep out and punch holes in the enemies defenses. That's how he won the Battle of Issus against a much larger Persian force, perhaps his greatest accomplishment.

How He Went Out: To this day, it's unclear what ended Alexander the Great at the age of 32. Some said malaria, others said poison. His armies had already reached into India, and he was planning an invasion of Arabia; who knows what he might have accomplished had he lived. Maybe he would have eventually lost a battle.

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Julius Caesar is listed (or ranked) 2 on the list Which General Would Win In An All-Out War Between History’s Greatest Military Leaders?
Photo: Angel M. Felicisimo/Wikimedia Commons/CC BY 2.0

Where And When: Born in 100 BCE, Julius Caesar rose to the heights of Roman society both through the luck of his birth, and his incredible usefulness as a military commander. He was responsible for the conquest of Gaul and the strengthening of the Roman legions. This, in turn, allowed him to achieve supreme political power and to become the unchecked ruler of the empire he had such a big hand in forging.

Win/Loss Ratio: 93.75% (15 wins, 1 loss)

His Greatest Achievements: The conquest of Gaul, Caesar's greatest military achievement, was made possible through his shrewd use of military engineers. These were specialized groups that could quickly build powerful fortifications, seemingly overnight. This allowed the highly organized Roman army to fight as though fortified, even in wilderness battlefields.

How He Went Out: Politics got the better of Caesar, and he was stabbed in the Roman forum. His military career had ended after he thoroughly defeated the rebellious Pompeiian faction at the Battle of Pharsalus.

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Napoleon Bonaparte is listed (or ranked) 3 on the list Which General Would Win In An All-Out War Between History’s Greatest Military Leaders?
Photo: Antoine-Jean Gros/Wikimedia Commons/Public Domain

Where And When: The man who would be known as the "Master of Europe" was born a commoner in 1769. A lifelong military man, he rose through the ranks during the French Revolution and eventually became Emperor of France through a coup. This was the start of an explosive time for France, during which Napoleon's armies crushed the nations of Europe and stretched all the way into Russia, even sending expeditions into Egypt.

Win/Loss Ratio: 88.3% (38 wins, 5 losses - numbers that make him by far the most statistically successful general in world history)

His Greatest Achievements: His military innovations are too many to count here, but Napoleon's genius is synonymous with his success at the Battle of Austerlitz. Taking a huge risk, he ordered his army to retreat from the most defensible ground, giving the impression of fear and disorganization. Overconfident, his enemies pursued him, and they were crushed when Napoleon's hidden Third Corps joined the fray.

How He Went Out: After his famous and crushing defeat at the Battle of Waterloo, Napoleon was forced to abdicate. He entered into exile and perished on the Isle of Saint Helena, possibly from stomach cancer.

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Robert E. Lee is listed (or ranked) 4 on the list Which General Would Win In An All-Out War Between History’s Greatest Military Leaders?
Photo:  Wikimedia Commons (CC-BY)

Where And When: Robert Edward Lee was born in 1807, the son of a Revolutionary War hero. He was a lifelong military man, serving in the Mexican-American War and as superintendent of West Point. When the Civil War became inevitable, Abraham Lincoln offered Lee command of the Union's forces, but Lee turned him down, unwilling to fight against his fellow southerners.

Win/Loss Ratio: 57.14% (8 wins, 6 losses)

His Greatest Achievements: Lee's greatest single success was at the Battle of Chancellorsville, where Lee used brilliant flanking maneuvers to defeat a much larger Union force. However, Lee's strongest overall quality was his ability to sustain his army through the course of the battles, his wisdom in choosing targets and, above all, his ability to soften inevitable defeats at the hands of larger and better equipped Union armies.

How He Went Out: Lee surrendered to General Ulysses S. Grant at the Appomattox Court House in April 1865. This came after a long campaign during which the much larger Union army hunted and harried Lee's troops, whittling them down. That they lasted so long is a testament to Lee's strategic brilliance.

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