1. The Battles of Heraclea and Asculum

The original Pyrrhic victory came courtesy of Pyrrhus of Epirus, a Greek king who was undone by his costly battles against the Romans. Pyrrhus first invaded Italy in 280 B.C. after allying himself with Tarentum, a Greek-speaking city that resented the Roman Republic’s increased domination over their homeland. He arrived with a force of some 25,000 men and 20 war elephants—the first the Roman legionaries had ever faced—and immediately scored a famous victory in his first battle at Heraclea. The following year, he bested the Romans a second time during a heated clash at Asculum.

Pyrrhus fancied himself a latter-day Alexander the Great, and he’d hoped his invasion would give his empire a foothold in Italy. But while he’d routed the Romans at both Heraclea and Asculum, he had also lost more than 7,500 of his most elite fighters, including many officers. Pyrrhus had no way of replacing his casualties, and his failure to deal the enemy a deathblow sent morale plummeting within his ranks. According to the ancient historian Plutarch, the warrior king was quoted as muttering, “If we are victorious in one more battle with the Romans, we shall be utterly ruined.” Following a setback at the Battle of Beneventum in 275 B.C., he reluctantly called off his campaign and sailed back to Greece.

2. The Battle of Malplaquet

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Getty Images / DeAgostini
The Duke of Marlborough gives orders during the battle of Malplaquet.

After King Charles II died without an heir in 1700, the War of the Spanish Succession erupted over who would assume his place on the Spanish throne. The struggle reached a bloody zenith at 1709’s Battle of Malplaquet, where an alliance of some 100,000 Dutch, Austrian, Prussian and British fighters under the Duke of Marlborough met a 90,000-strong French army. Marlborough was eager to crush the French forces, and on September 11, he launched a massive infantry and cavalry assault. The French had fortified themselves in a maze of entrenchments and obstacles, and it took seven grueling hours before the alliance finally punched through their lines and seized their works. By then, Marlborough’s battered soldiers were too exhausted to press their advantage. The French were able to make an organized retreat with much of their force still intact.

Malplaquet would go down in history as the deadliest battle of the 18th century. The French suffered some 12,000 casualties, while Marlborough lost 24,000 men—nearly a quarter of his entire army. In a nod to Pyrrhus of Epirus, the French commander Claude de Villars is said to have told King Louis XIV, “If it pleases God to give your enemies another such victory, they are ruined.” Along with leading to the removal of Marlborough, the bloodbath at Malplaquet helped sow the seeds of disunion within the anti-French alliance. By 1712, it had started to collapse.

3. The Battle of Bunker Hill

The American Revolution had turned bloody by the summer of 1775, but aside from minor skirmishes at Lexington and Concord, the colonials had yet to test their mettle against the British Army. That changed on June 17, when a ragtag group of 1,000 militiamen tried to check a British advance on the heights overlooking Boston. After fortifying Breed’s Hill—the battle takes its name from Bunker Hill, the peak they were originally told to occupy—they faced down a superior force of some 2,200 British soldiers. The Americans’ accurate musket fire drove back two separate British attacks, but by the third advance, they had expended their meager stores of ammunition. Following a few frantic minutes of hand-to-hand combat, the militiamen abandoned the hill and retreated.

The British victory at Bunker Hill came at a punishing cost. Compared to 400 killed or wounded for the colonials, the Redcoats sustained more than 1,000 casualties, and their heavy losses forced them to scrap plans to seize another piece of high ground on the outskirts of Boston. The Americans, meanwhile, hailed the defeat as a moral victory. They had gone head-to-head with a larger and better-equipped enemy, and had shown they would not be beaten without a fight. While British General William Howe lamented that his success had been “too dearly bought,” patriot leader Nathanael Greene wrote that he wished the colonials could “sell them another hill at the same price.”

4. The Battle of Borodino

The single bloodiest day of Napoleon Bonaparte’s military career unfolded on September 7, 1812, when the French emperor was in the midst of his doomed invasion of Russia. During the early stages of the campaign, the Russian Imperial Army had been content to stage tactical retreats, and Napoleon’s Grande Armée had advanced to within striking distance of Moscow. But when the French neared the small village of Borodino, Russian commander Mikhail Kutuzov finally turned his army around, constructed fortifications and prepared to make his stand. Napoleon wasted little time.

In a typically aggressive fashion, he threw 130,000 soldiers against the Russian lines in a frontal assault. Kutuzov’s men responded with a series of brash counterattacks, and the battle hung in the balance until late afternoon when the French finally claimed the main Russian redoubt. Napoleon was reluctant to send his elite Imperial Guard into the fray, however, and Kutuzov’s army managed to escape destruction and flee.

Napoleon was left in full control of the battlefield, but it was a ground littered with French bodies. His Grande Armée had suffered some 30,000 casualties—a full 15,000 fewer than the Russians, but far too many to be sustainable when fighting on unfriendly soil. The situation only worsened when Napoleon moved on Moscow a few days later. He found his victory prize largely abandoned, and shortly after his arrival, the Russians set fires that burned much of the city to the ground. Napoleon called off the campaign a month later, but his retreat was dogged by the Imperial Army and the frigid Russian winter, both of which took their toll. By the time the French finally escaped from hostile territory, they had suffered a total of some 40,000 casualties.

5. The Battle of Chancellorsville

Few Civil War battles demonstrate General Robert E. Lee’s tactical genius more than his May 1863 victory at Chancellorsville, Virginia. Despite being outnumbered 2-to-1 by General Joseph Hooker’s troops, Lee took a huge gamble—and disregarded all military doctrine—by twice dividing his forces and taking the fight to the enemy. His bold strategy dashed Hooker’s hopes of enveloping the Army of Northern Virginia, and ultimately forced the Union commander to withdraw across the Rappahannock River in disgrace.

While Chancellorsville is often called Lee’s masterpiece, it came with a massive price tag. The Confederates sustained a crushing 13,000 casualties, including the friendly fire death of Stonewall Jackson, the brilliant general that Lee had called his “right arm.” The Union Army of the Potomac suffered an even greater 17,000 killed, wounded and captured, but unlike the rebels, it had the manpower and recruitment numbers to replace its losses. More importantly, it had escaped destruction and lived to fight another day. Just two months after Chancellorsville, it would meet Lee again at the battle that is often called the turning point of the war: Gettysburg.

HISTORY Vault: Napoleon

Explore the extraordinary life and times of Napoleon Bonaparte, the great military genius who took France to unprecedented heights of power, and then brought it to its knees when his ego spun out of control.