10 of History’s Cleverest Generals – And How They Used Their Wits To Change The World

February 8, 2023 People's Tonight 608 views

M. Muir

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.


• Photo: Ny Carlsberg Glyptotek / Wikimedia Commons / CC-BY-SA 4.0

Scipio Africanus Saved Rome From Disaster

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.

o Age: Dec. at 53 (235 BC-182 BC)

o Birthplace: Rome, Italy

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• • • Photo: Unknown / Wikimedia Commons / Public domain

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

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• • Photo: Antoine-Jean Gros / Wikimedia Commons / Public domain

Napoleon Bonaparte Knew When To Go All-In

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

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• • Photo: Phaidon Verlag (Wien-Leipzig) / Wikimedia Commons / Public domain

Hannibal Was Ancient Rome’s Worst Nightmare

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

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• • Photo: Unknown / Wikimedia Commons / Public domain

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.

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• • Photo: Kanō Mitsunobu / Wikimedia Commons / Public domain

Toyotomi Hideyoshi Found Unique Ways To End Sieges

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

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• • Photo: Miguel Hermoso Cuesta / Wikimedia Commons / Public domain

Seleucus Succeeded Where Alexander Failed

When the experienced general Parmenion suggested a night attack on the Persians before the Battle of Gaugamela, Alexander the Great pointedly refused to “steal” his victory. Those who came after him had no such qualms, however. His most successful Diadochi (“successors”), Ptolemy and Seleucus, used treachery freely to carve out empires that lasted much longer than Alexander’s.

Seleucus was nowhere near the top dog when Alexander perished in 323 BCE. With only a single province to his name, Seleucus had to be smart, and honor was a luxury he couldn’t afford. His first piece of treachery was to stab Perdiccas in the back in Egypt, a favor Ptolemy repaid when Seleucus was forced away from Babylon by Antigonus.

He regained his domain a year later and then defeated a much larger army sent against him by using the very tactics Alexander scorned before Gaugamela. His deftly executed nocturnal strike eliminated his enemy’s leaders, but without doing a great deal of damage to the regular soldiers; he promptly absorbed those men into his own ranks. Seleucus then used the cover of the night once more to defeat Antigonus and cement his hold in the east.

His intelligence as a leader was also apparent in his diplomacy. Knowing when to fight and when to cut a deal is an overlooked part of being a smart leader. When things weren’t going his way against Chandragupta, Seleucus made a sensible deal that worked out for both parties: 500 elephants for the eastern provinces. The subsequent good relations between the two men helped each leader concentrate efforts elsewhere. Seleucus made and broke alliances as it suited him and was the last of the original Diadochi standing. It was perhaps quite fitting that he would fall victim to treachery in the end.

He wasn’t the most honorable of history’s generals, but was certainly one of the smartest.

• Age: Dec. at 77 (357 BC-280 BC)

• Birthplace: Macedonia

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• • Photo: Gilbert Stuart / Wikimedia Commons / Public domain

George Washington Kept The British At Bay For Years

As the general of the Continental Army, George Washington was up against the might of the British Empire with limited support. For eight long years, he kept his army in the field, time and again narrowly avoiding disaster through clever tactics and shrewd management. Of his many gifts as a commander, one of his most important was attention to detail.

Before the American Revolution, he cut his (famously not-wooden) teeth as a leader in service to the British in the French and Indian War. Though he only ever commanded relatively small numbers of men, he learned valuable lessons for the future.

The first was the importance of discipline in his men; Washington would describe the term as “the soul of an army,” and in the days of rank-and-file warfare, discipline was the difference between a setback and annihilation. He also learned the value of adapting to terrain and the vital importance of the welfare of his men. Several years later, he would demonstrate this value with the mass inoculation of his troops against smallpox, a decisive and crucial measure to keep his men in the field.

Against a superior force in the British, Washington successfully avoided major defeats while sapping the will of the redcoats, a strategy actually quite similar to how the Romans dealt with Hannibal in the Second Punic War. The Continental Army was very nearly done for after a loss at the Battle of Long Island, surrounded by British General William Howe’s men, the end seemed nigh. However, Washington whisked his men away under the cover of darkness to Manhattan. He used subterfuge to keep his opponents guessing, making them think he had far more men than he really did.

River crossings became something of a signature move for the general; in the difficult winter of 1776, he unexpectedly crossed the Delaware River on December 26 to catch a group of mercenaries off guard. Not one to push his luck, he retreated back across with his captives. A few days later he once again crossed the Delaware to face off against Lt. Gen. Charles Cornwallis’s army. After three British assaults were pushed back, Cornwallis decided to wait for the light of the next day to finish Washington off. When his men resumed the attack, they found the Americans were long gone.

For years, Washington kept the British at bay, all while battling against a Congress reluctant to do its fair share to keep the army supplied. Yet his shrewd leadership prevailed, and the army kept up the fight long enough for the French and Spanish to enter the fray and turn the tide. Under a less capable leader, the revolution may never have come to fruition.

• Age: Dec. at 67 (1732-1799)

• Birthplace: Virginia, United States of America

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• • Photo: Hnc197 / Wikimedia Commons / CC BY-SA 2.5 

Yi Sun-Sin Saved Korea With Minimal Losses

When Japan invaded Korea toward the end of the 16th century, the outlook was bleak. Against tens of thousands of battle-hardened samurai stood an untested and largely peasant Korean military.

The initial onslaught was distinctly one-sided; Seoul was captured within 19 days and it seemed the kingdom would soon fall. Things might have been going poorly on land, but at sea, the Korean navy more than held its own, thanks to the leadership of Yi Sun-sin.

Yi wasn’t actually a naval leader by training; his career before the Japanese incursion had been spent holding back raiders in the border forts to the north. A consummate professional, Yi took to naval warfare like a duck to water. He trained and drilled his men into an efficient fighting force with a heavy focus on keeping the Japanese ships at a distance and preventing them from boarding. He won a string of great victories with minimal losses, which helped slow down the Japanese incursion as supply lines were cut and the initial momentum was lost.

His work was very nearly undone by an intrigue instigated by a rival; Yi was ousted from his command and his successor lost all but 13 ships in a disastrous defeat. After being restored to command, Yi refused to scuttle the fleet and instead engaged a Japanese fleet 10 times larger than his own at Myongnyang. He used the confines of the strait to his advantage to bottle up the Japanese ships and maximize the firepower of his fleet. What was supposed to be a defiant last stand instead became a remarkable victory, as the Japanese fleet just couldn’t lay a glove on the determined Korean flotilla.

A year later, as the Japanese prepared to pull out of Korea, Yi’s fleet along with allies from Ming China inflicted yet another defeat on the Japanese. It proved to be Yi’s final battle; never one to shirk danger, he was mortally wounded by a stray bullet and taken below decks. His nephew put on his armor and oversaw the victory disguised as his uncle. Yi is regarded today as a national hero in Korea.

• Age: Dec. at 53 (1545-1598)

• Birthplace: Hansung

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• • Photo: After Samuel Cooper / Wikimedia Commons / Public domain

Oliver Cromwell Brought Professionalism To The Military

He might not have taken his first military command until he was 40, but Oliver Cromwell was a natural leader who helped to transform the British army. He was a cavalry officer in the first English Civil War who rose quickly through the ranks.

After some early setbacks for the parliamentary side, Cromwell oversaw the creation of the New Model Army in 1645 to address the systemic failures within the military; it was formed as a professional force under a single commander, with leaders chosen on merit rather than wealth and connections. The Parliamentarian leaders removed themselves from contention to lead in the field in April 1645. Cromwell assumed command of the cavalry and played a key role in the victory at Naseby.

It was in the Second English Civil War (1648-49) that Cromwell truly made his mark as a leader. Now the head of the New Model Army, he won an outstanding victory at Preston in Lancashire against a numerically superior Scottish army. This was followed by an incursion into Ireland to root out support for the deposed Charles II. Cromwell is still villainized in Ireland to this day for his brutal excesses during the campaign.

The third and final phase of the English Civil War saw Cromwell achieve arguably his greatest victory at Dunbar, Scotland, when his New Model Army invaded their northern neighbor in the summer of 1650. He outmaneuvered a larger Scottish army with his cavalry and used a combination of artillery, horses, and infantry to inflict a decisive defeat upon the supporters of Charles II.

His last battle took place a year later, another lopsided triumph, this time at Worcester.

Cromwell became Lord Protector of the Commonwealth in 1653 and ruled as a military dictator until his demise five years later. As ruthless as he was brilliant, there is little doubt he ranks among the cleverest generals in history.

• Age: Dec. at 59 (1599-1658)

• Birthplace: Huntingdon, United Kingdom

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