10 Of History's Cleverest Generals - And How They Used Their Wits To Change The World



Copy link

List Rules

Vote up the cleverest leaders in history.

The general, as one famous ancient text on warfare put it, is “the arbiter of the people’s fate, the man on whom it depends whether the nation shall be in peace or in peril.” 

Few attributes have decided success or failure in military matters quite like wisdom. Stupidity can throw away even the greatest advantages in men, firepower, and technology. It is the cleverest generals who can innovate, inspire, or just find a way out of a jam nobody else could see. 

This collection looks at a diverse array of some of history’s smartest military minds, from the Japanese warlord who could end a siege with minimum fuss to the cruel but gifted English amateur who transformed his country’s military forever.

  • Scipio Africanus Saved Rome From Disaster
    Photo: Ny Carlsberg Glyptotek / Wikimedia Commons / CC-BY-SA 4.0

    Publius Cornelius Scipio was the Roman general who helped turned the tide in the Second Punic War, coming to the Republic’s aid during its darkest hour. He assumed command of a Roman army at the age of just 24, following his father’s untimely demise. Rather than confront Hannibal directly in Italy, the young Scipio headed to Iberia to destroy the Carthaginian base in Spain and stop the flow of supplies and reinforcements to Hannibal. At the Ilipa River he pulled off a ruse Hannibal would have been proud of.

    Day after day the Roman and Carthaginian forces lined up against one another without giving battle. Each time Scipio placed his weakest troops - local Spanish mercenaries - on the flanks. That was until the seventh day when Scipio woke his men up early and put his best troops on the wings. By the time the Carthaginians spotted the switch, the Roman army was upon them. The Spanish troops simply held fast, preventing the best Carthaginian troops from moving to aid the collapsing flanks. Scipio followed up on this triumph and soon secured Iberia for Rome. He then launched the decisive incursion into Africa that forced Hannibal to abandon his Italian expedition to protect Carthage.

    Military leadership is not just about winning on the battlefield; it’s also in the careful management of an army and one’s allies. In this, Scipio showed wisdom beyond his quite tender years. One of Rome’s great weaknesses lay in a lack of cavalry; Scipio solved this by persuading a Numidian prince, Massinissa, to switch sides and bring his elite horseman to the Roman cause. This would prove vital at the battle of Zama, where Scipio’s army prevailed over Hannibal thanks to a large extent to Massinissa’s cavalry. 

    Scipio was honored with the name by which he is remembered today: Scipio Africanus. 

    • Age: Dec. at 53 (235 BC-182 BC)
    • Birthplace: Rome, Italy
    82 votes
  • Subutai Was The Master Of Movement
    Photo: Unknown / Wikimedia Commons / Public domain
    77 VOTES

    Subutai Was The Master Of Movement

    For the Mongols, military excellence wasn’t the exception, but the rule. Unlike most of their contemporaries, the Mongols selected generals on merit. If he was capable enough, the sky was the limit for a Mongol warrior. This resulted in first-rate officers and generals who were light-years ahead of their peers. The very best of the excellent leaders was a man named Subutai

    One of Genghis Khan’s earliest followers, Subutai (also spelled Subotai) rose to become his most trusted and able general. He won 65 pitched battles and oversaw 20 campaigns ranging from China to Russia to the steppes of Hungary. It’s sometimes said the first rule of war is not to march on Moscow - well, Subutai did, and he did in the winter. Only the sudden death of the Khan pulled him away from continuing his European conquests.

    Subutai was a flexible leader capable of coordinating multiple armies hundreds of miles apart, with methods of command and control far ahead of their time. His troops would spread out over vast distances to ransack the kingdoms before converging to smash whatever opposition gathered against them - when the enemy least expected it. 

    The tough victory at Mohi showcased his ability to work out clever solutions on the fly and see a plan through. When a Mongol river crossing was caught and repelled by the Hungarians armed with crossbows, the Mongols returned with stone throwers to force a path through. At the same time, Subutai organized the construction of a makeshift bridge downstream. 

    After a hard day’s fighting, the Hungarians were pushed back into their camp. Subutai left a gap in the Mongol lines to tempt them to try to escape in the night. It was an idea right out of the Art of War, and it worked:

    When you surround an army, leave an outlet free. Do not press a desperate foe too hard. 

    Fleeing soldiers are much easier game than those surrounded and fighting to the finish. Subutai's grasp of operational warfare places him at the very top of history's greatest generals.

    • Age: Dec. at 72 (1176-1248)
    • Birthplace: Burkhan Khaldun, Mongolia
    77 votes
  • Napoleon Bonaparte Knew When To Go All-In
    Photo: Antoine-Jean Gros / Wikimedia Commons / Public domain

    Napoleon was one of history’s most innovative military leaders. He fought more than 60 battles and emerged the victor in the vast majority, often against much larger armies. It took multiple coalitions of Europe’s foremost powers working together to finally topple the French emperor, and even then, it was still an incredibly close-run match.

    What made Napoleon so successful as a leader was his ability to keep his opponent guessing and then bring his forces together to deliver the decisive blow. His greatest victory, Austerlitz, highlighted his talents as a leader. He used deception to bring about a battle on his terms by appearing weaker than he really was. It’s unlikely he ever had a chance to flip through Sun Tzu’s The Art of War, but his plans perfectly encapsulated the ancient text’s advice for fighting on favorable terms:

    Hold out baits to entice the enemy. Feign disorder, and crush him.

    Napoleon feigned a retreat to his chosen ground and kept his right flank weak to invite the Russian and Holy Roman Army to attack. As they pivoted to overwhelm the French right flank, Napoleon waited for the optimal moment to launch his main strike at the Austro-Russian center. As he ordered the attack of the 16,000 men under Marshal Nicolas Soult, Napoleon remarked:

    One sharp blow and the war is over.

    The attack smashed through the middle of the enemy army as planned. By the time the dust had settled, the Austro-Russian army was in tatters; 36,000 men were killed or captured. It was the crowning achievement of a remarkable career.

    • Age: Dec. at 51 (1769-1821)
    • Birthplace: Ajaccio, France
    76 votes
  • Hannibal Was Ancient Rome's Worst Nightmare
    Photo: Phaidon Verlag (Wien-Leipzig) / Wikimedia Commons / Public domain

    The Carthaginian general Hannibal Barca was easily Rome’s most capable adversary. During the Second Punic War, he brought the Roman Republic to the brink of catastrophe through a series of brilliant battlefield victories. Only Roman stubbornness and the eventual emergence of a Hannibal of their own, Scipio, prevented Carthage from assuming its place as the foremost power in the ancient Mediterranean world.

    Hannibal’s signature moves were taking surprising routes and turning his opponent’s strengths into weaknesses with clever tactics. He took an unexpected route through the Alps to bypass the forces mustered against him in northern Italy. When he reached the other side of the mountains, he overcame a Roman army with a carefully executed plan by baiting the Romans into a river crossing and then using a hidden detachment to smash into the Roman rear.

    He followed that up with an ambush at Trasimene, but by far his greatest triumph was the reverse encirclement at Cannae. Against a much larger army, Hannibal placed his best troops on the flanks while personally taking command in the center to prevent his weaker troops from breaking. 

    His lines were pushed back, and just as it seemed the Romans were going to push through, he sprung his trap. As his superior cavalry gained the upper hand, his elite infantry turned on the flanks of the Roman army while the horseman wheeled back to smash into the exposed back of the Romans. The surrounded Romans were annihilated in one of military history’s greatest-ever accomplishments.

    • Age: Dec. at 64 (246 BC-182 BC)
    • Birthplace: Carthage, Tunisia
    54 votes
  • Julius Caesar Took Huge Risks But Always Had An Ace Up His Sleeve
    Photo: Unknown / Wikimedia Commons / Public domain
    56 VOTES

    Julius Caesar Took Huge Risks But Always Had An Ace Up His Sleeve

    In matters, both military and political, Julius Caesar was a gambler first and foremost. But his habitual risk-taking was backed up by a tendency to have a trick or two up his sleeve. During his conquest of Gaul, he finally cornered Vercingetorix, the leader of the uprising, at the fortress city of Alesia

    Rather than needlessly throw away the lives of his men, he built a ring of siegeworks around the settlement to starve his enemy out. As the siege was progressing, he got wind of a huge army (improbably claimed to be 250,000-strong by Caesar’s account) being sent against him to relieve Vercingetorix. Rather than give up the prize, he ordered a second ring of fortifications to be built - around his own men. 

    It proved to be a master stroke, as the siegeworks prevented the two Gaulish armies from linking up and destroying Caesar’s army. It was still a hard-fought victory all the same, but Caesar’s improvised solution effectively ended the Gallic Wars. 

    With each success came a more brazen risk; after putting an end to the Gauls, Caesar crossed the Rubicon with just a single legion to ignite a civil war. The decisive battle took place in Greece at Pharsalus. Up against the forces led by the formidable general Pompey. Caesar was outnumbered and running low on supplies but took to the field with an elite army of battle-hardened veterans and a clever trick up his sleeve. 

    He had to stretch his lines to match the Republican army’s vast numbers, but he knew they could hold the line long enough to execute his plan. He kept a hidden line of infantry behind his cavalry that he used to break Pompey’s far more numerous horsemen. The trap was sprung and Pompey’s cavalry was driven from the field, exposing the army’s left flank. With the breach opened, Caesar poured in his best troops, causing a chain rout of Pompey’s army and securing Caesar’s greatest victory.

    56 votes
  • Toyotomi Hideyoshi Found Unique Ways To End Sieges
    Photo: Kanō Mitsunobu / Wikimedia Commons / Public domain

    Toyotomi Hideyoshi was a Japanese warlord who rose from humble beginnings to become the master of Japan during the Sengoku period, a century-long era of incessant warfare between rival warlords, lasting from the mid-1400s to the mid-1500s. He started out as a retainer for Oda Nobunaga and swiftly rose through the ranks, as he was adept at finding creative solutions to problems and minimizing his own losses.

    At the siege of Tottori, for example, he took the seemingly impregnable fortress by purchasing the province’s rice at an inflated price to starve out the garrison with minimal losses. At Takamatsu, he diverted a nearby river to flood the surrounding plain and used ships to whittle down the walls. As he was nearing the end of that siege, he learned his master and mentor had been slain by a treacherous subordinate. 

    Quick as a flash, he rallied his men and toppled Akechi Mitsuhide by riding through the night and surprising his army. He then picked up where Oda left off by conquering the rest of Japan. Unlike his predecessor, he showed clemency to beaten rivals, and then used them in his next conquest. After defeating the Chosokabe in Shikoku, they became the vanguard of his Kyushu expedition the following year.

    In winning without incurring great losses and using overwhelming force against his remaining foes, Hideyoshi was essentially modeling the ideal generalship outlined by Sun Tzu:

    What the ancients called a clever fighter is one who not only wins, but excels in winning with ease.

    Hideyoshi's last battle was the unwinnable struggle against time. As he neared the end of his life, he tried to secure his young son’s succession. Little Hideyori was only 6 when Hideyoshi passed. After biding his time for decades, Tokugawa Ieyasu made his move. While Hideyoshi didn’t establish a lasting dynasty, his astonishing rise from peasant to the ruler of Japan in an era rife with treachery and danger was an incredible achievement made possible by his shrewdness.

    • Age: Dec. at 61 (1537-1598)
    • Birthplace: Nakamura-ku, Nagoya, Japan
    44 votes