10 of History’s Worst Military Blunders

by Marcus Ribeiro

Military history is filled with tales of deceptions, feints, surprise attacks, envelopments, double-crosses, and other brilliant maneuvers by brilliant generals. But it’s also filled with stories of overconfident commanders biting off way more than they can chew with foolish invasions, attacks on superior enemies, and ignoring all sorts of red flags that might have spared countless lives. Let’s take a look at some of the most infamous military blunders in history. 

10. Napoleon’s invasion of Russia

Like every successful conqueror, Napoleon Bonaparte eventually became too ambitious for his own good. His attempts to force Spain and Russia to cut off trade with Britain both became military disasters for him. But of the two, the invasion of Russia was far worse. 

Napoleon’s Grande Armee marched into Russia with a force of between 650,000-700,000 men, unprecedented in world history at the time. But the Russians wisely opted to retreat rather than face him, employing scorched earth tactics along the way and thus forcing Napoleon’s army to rely on an increasingly shaky supply line. He did win the bloody Battle of Borodino and took empty, burning Moscow shortly afterwards, but the expected Russian surrender never materialized. With winter setting in, Napoleon had no choice but to take his remaining men on a torturous retreat. En route, his already mauled army took further losses from disease, starvation, freezing temperatures, and cossack raids. Well under 100,000 French troops made it out alive. It was a humiliating, mutilating defeat from which Napoleon never fully recovered. It shattered the myth of his invincibility and set the stage for his first abdication in 1814. 

9. Germany declares war on the US 

Nazi Germany was at the peak of its power in 1941. France had been overrun in a stunning six week campaign the year before. Britain was thrown into the sea in the same attack and now unable to challenge the Wehrmacht in continental Europe. And in Russia, the Soviets had taken titanic losses, and German legions were at the doorstep of Moscow. 

Just then, Japan attacked Pearl Harbor on December 7, dragging the US into the war. Hitler could have laid low. Who knows? Maybe America’s preoccupation with Japan would’ve led to them reducing the desperately needed Lend-Lease supplies keeping Britain and the USSR afloat, to funnel into their own war effort. 

Instead, an overconfident Hitler, fully convinced he would be able to finish off Britain and Russia before America was done with Japan and able to send armies to Europe, decided to declare war on the US. It was a symbolic show of solidarity with Germany’s Axis partner Japan. But it would be a disastrous decision. The “Germany first” policy of the Allies took him by surprise, and German defeats in Russia soon paved the way to the thing Hitler dreaded most: an unwinnable two-front war. 

8. Lee blows it at Gettysburg 

The Confederates at least appeared to be winning the American Civil War in 1863, thanks to victories in Virginia. But in reality, the Emancipation Proclamation slamming the door on the possibility of international recognition for the South, combined with a Union blockade and the impending fall of vital Vicksburg on the Mississippi, had the rebels in desperate straits by that summer. Army of Northern Virginia commander Robert E. Lee decided to take his smaller but highly confident army on its second invasion of the north that June, hoping to win a major victory on Union soil that would scare a war-weary north out of the war. 

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This led to the Battle of Gettysburg in early July. Union troops were defeated on the first day, but able to seize and successfully defend high ground on July 2. Knowing he would likely never get another shot at a major northern victory, Lee launched a massive infantry assault called Pickett’s Charge on July 3. It was doomed from the start, and the devastated Southern army never fully recovered. Lee never won a major victory again. Less than two years later, he surrendered his tiny army at Appomattox, all but ending the war. 

7. Custer gets slaughtered at Little Big Horn

George Armstrong Custer was a respected Union cavalry commander during the American Civil War, but he’s not remembered for beating J.E.B. Stuart at Gettysburg. He’s remembered for his ill-fated, and last, performance, at the Battle of Little Bighorn in 1876. Custer, a flamboyant and ambitious cavalry officer, underestimated the strength of the Native American forces he faced and made a series of critical errors that led to a devastating defeat for the US Army.

Custer’s first mistake was a lack of proper reconnaissance. Overconfident and desperate for glory, he divided his forces into three separate battalions without adequate information about the size and positioning of the Lakota Sioux, Cheyenne, and Arapaho tribes he intended to engage. On June 25-26, 1876, Custer’s 7th Cavalry encountered overwhelming resistance. Instead of waiting for reinforcements or adopting a more defensive stance, Custer pressed forward into a situation where his troops were outnumbered, outgunned, and, ultimately, surrounded and destroyed. 

“Custer’s Last Stand” has become one of the biggest cautionary tales in military history. 

6. Rome gets annihilated at Cannae

The story of the 216 BCE’s Battle of Cannae is usually told from the perspective of Carthaginian general Hannibal Barca’s brilliant double envelopment and slaughter of tens of thousands of Roman soldiers, during his Second Punic War invasion of Italy. But it’s worth examining the degree to which the Romans brought the disaster on their own head, too. 

In a nutshell, the Romans got their cavalry wiped out and then, overconfident in their heavy infantry, shrugged it off and marched straight into the Carthaginian lines. Hannibal wanted this – he feigned weakness and ordered his men to slowly withdraw, keeping the Romans preoccupied with splitting his line in half. By the time they realized it was a trap, it was too late. The Carthaginians stopped retreating, snapped their flanks in, and used their cavalry to seal the last remaining escape route. Surrounded, the Romans lost some 70,000 men in one day, an unimaginable death toll. Given Rome’s population at the time, that would be the equivalent of America losing tens of millions of men in one day. 

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Watch your flanks, people. And don’t underestimate any enemy, especially those who had already beaten you multiple times before. 

5. Japan attacks Pearl Harbor

Pearl-Harbor

Japan’s brutal invasion of China didn’t lead to a swift victory. What it did lead to was their army getting bogged down there and their supplies of oil, steel, and rubber being cut off by an American embargo. 

Japan realized it could get its own sources by seizing resource-rich territory throughout Southeast Asia. But that would lead to inevitable war with Britain, the Netherlands, and the United States, who owned that land. But they rolled the dice and invaded all that land anyway. As part of this offensive, they decided to preemptively remove their greatest naval competitor in the Pacific, with a sneak attack on the US Pacific fleet at Pearl Harbor, Hawaii. 

They knew America had overwhelming industrial might, but hoped that by the time America recovered, they would’ve already conquered China and would be so entrenched throughout the Pacific that America would sue for peace, realizing the cost of removing Japan was too high. It was a ludicrous gamble. The Americans were enraged but far from crushed in the attack. They turned the tide at Midway mere months later, and then slapped aside every Japanese attempt to stop them as they smashed their way to the home islands. Oops! 

4. The Battle of Fredericksburg

By December 1862, the American Civil War had raged for a year and a half – far longer than either side had anticipated. And it was only getting bloodier by the day. Part of the overall Union plan was, in addition to seizing the Mississippi River and blockading Southern ports, to capture the Confederate capital of Richmond, Virginia. The Union Army of the Potomac had failed repeatedly at this task, but was determined to get it right. 

Under extreme pressure from president Lincoln, new commander Ambrose Burnside (after whom sideburns were named) decided to cross the Rappohanock River at Fredericksburg, Virginia, and then march south to Richmond. But pontoon boats were slow in arriving, giving General Robert E. Lee a chance to guess his opponent’s intentions and swiftly fortify his positions. His subordinate Stonewall Jackson had some difficulty in his sector, but James Longstreet held the line masterfully at Marye’s Heights, inflicting appalling losses on Union brigades that walked straight into the teeth of a rebel stone wall. It was one of the worst Union defeats of the war, and no major attempts were made to march on Richmond for nearly a year and a half afterwards. 

3. Charge of the Light Brigade 

It’s been immortalized and glorified by Lord Alfred Tennyson’s famous poem of the same name, but the real charge of the light brigade, which took place during 1854’s Battle of Balaclava during the Crimean War, was far from glorious. The charge occurred when a miscommunication led the Light Brigade, a British cavalry unit, to charge directly into a well-defended position. 

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The confusion that led to the Charge of the Light Brigade began when an order was given by British commanders. Due to unclear communication and misinterpretation, the Light Brigade, under the command of Lord Cardigan, advanced into the “Valley of Death” against a heavily fortified Russian artillery position. The brigade faced fire from both sides as they galloped headlong into a devastating crossfire. It was old school military glory versus the harsh reality of modern military killing machines. The resulting carnage foreshadowed the carnage of the First World War.

2. Gallipoli campaign

Combat in World War I heavily favored the defender, leading to static front lines and lots of dead men who tried to breach them. Seeking a way to break the stalemate, Entente (Allied) leadership sought to attack one of Germany’s perceived weaker partners, the Ottoman Empire. 

Future WW2-era British Prime Minister Winston Churchill, then a high-ranking Naval strategist, concocted a plan to devastate the Ottomans and make contact with their Russian allies by forcing the Dardanelles straits near Istanbul. They would charge into the bay with older wooden warships as the vanguard, hoping these less valuable vessels would do as much damage as they could while absorbing Ottoman fire and nautical mines. After the Ottomans were tired and running low on ammo, newer metal warships would cruise in, finish off the defenders, and deposit infantry to capture the area. 

Unfortunately, it all fell apart. Commanders overly attached to their beloved wooden boats protected them from fire, exposing the rest of the fleet. And the infantry got bogged down on Gallipoli with no way forward for months, facing murderous Ottoman fire until they were evacuated in 1916, having achieved nothing of strategic value. 

1. Invasion of Canada

We could go on and on about how dumb the War of 1812 was. But the invasion of Canada by US forces was arguably the silliest and stupidest chapter in it. In the early stages of the war, the United States sought to annex British-held territory (a longterm policy goal for many Americans politicians) initiated a three-pronged invasion plan targeting Upper Canada (present-day Ontario), Lower Canada (present-day Quebec), and the maritime provinces. 

The Americans faced initial success with victories at Detroit and the capture of Fort Mackinac. But the campaign ultimately faltered as underprepared American forces, stuck with horrible intelligence and worse leadership, encountered logistical challenges, harsh weather conditions, and strong resistance. The Battle of Queenston Heights in October 1812 proved a significant setback for the Americans, as their attempts to invade Upper Canada were repelled.

In 1813, both sides engaged in a series of offensives and counter-offensives before the Americans finally called it a day and returned home, solidifying much of the US-Canada border we still have today. Canadians still cheer about it, and it’s hard to blame them. Meanwhile, Americans would rather change the subject.

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