15 Embarrassing Military Decisions That Lost Battles & Wars main image
Scroll Down To Continue

15 Embarrassing Military Decisions That Lost Battles & Wars

History is packed with fascinating moments, especially when it comes to military strategy. We tend to think of military leaders as sharp and meticulous, and with good reason—decisions made in battle can mean the difference between life and death. However, not every general makes wise choices. In fact, some have committed disastrous errors that have cost battles, and even entire wars.

Anyone passionate about history can recount conflicts that were fought unnecessarily or could have been avoided. A classic example is Operation Barbarossa, where German forces launched an ill-fated attack on the Soviet Union in the middle of winter. It’s now infamous.

We'll explore other catastrophic military blunders that led to tragic consequences. In some cases, these mistakes may have even contributed to the downfall of entire empires! While it’s impossible to predict how things might have turned out if these battles had gone differently, it’s safe to say some leaders were left regretting their choices. Here are some of history’s most notorious military miscalculations!

The Alamo

The Alamo

The Alamo was a total blunder. First of all, Texans weren’t even supposed to defend the Alamo. They were told to destroy the Alamo and return with the men and artillery stationed there. 

Second, the Texans could have escaped because the Santa Anna army didn’t block the exits. Finally, the Santa Anna army took a total of 10 days to defeat the Alamo despite the military being much, much larger.

(Image via Wikipedia)

The Soviet Invasion of Afghanistan

The Soviet Invasion of Afghanistan

Countries have been trying to invade Afghanistan for ages, and it doesn’t usually go too well. The Soviet Invasion attempted to invade the country in 1979, and the Soviets and Afghans battled it out for the next 10 years. 

The result was the death of 15,000 men and billions of rubles worth of equipment that was lost in Afghanistan. This war also led to the rise of the Taliban.

(Image via Wikipedia)

The Vietnam War

The Vietnam War

American involvement in the Vietnam War was a huge mistake. It was reportedly fought to keep communist power from spreading, but it just ended up bloody and ugly. 

It’s estimated that the United States lost over 58,000 soldiers during the war, and the country eventually fell to communism rule regardless. To make matters worse, it left people questioning if it was fought to crush the national liberation movement.

(Image via Wikipedia)

The Battle of Agincourt

The Battle of Agincourt

During the Hundred Years War, the battle of Agincourt should have been an easy French victory, considering that they had more men. However, the English surprised everyone with an upset victory. 

This battle is considered one of the most important British victories during the Hundred Years War. And it was even brought to life in the play Henry V by Shakespeare. 

(Image via Wikipedia)

The Bahia Self-Attack

The Bahia Self-Attack

You’d think a huge goal for most warships would be to avoid sinking themselves, but it happens more than you’d think. As World War II drew closer, a Brazilian cruiser, called the Bahia, was stationed outside of Brazil to protect Allied convoys. 

The crewmembers were practicing an anti-aircraft drill when a gunner accidentally hit an entire row of depth charges. Naturally, the charges exploded, the ship sank, and all but a few dozen of the 350 crewmembers survived. 

(Image via Wikipedia)

The Battle of Waterloo

The Battle of Waterloo

Napoleon's battle at Waterloo was such a spectacular failure that "meeting your Waterloo" became a cultural reference for someone who had experienced a decisive and humiliating defeat. Waterloo also inspired ABBA's first and strangest hit of the same name.

This battle marked the end of the Napoleonic Wars after his troops were defeated by soldiers from the UK and the Netherlands. After his humiliating defeat, Napoleon abdicated the throne (for a second time) and went into exile, where he died shortly after. 

(Image via Midjourney)

The Fall of Mosul

The Fall of Mosul

The fall of the Iraqi city of Mosul occurred in June of 2014 when ISIS forces successfully defeated the Iraqi army stationed in the city. The fall of Iraqi forces was a shock, considering how much they outnumbered ISIS. 

The Iraqi military had over 60,000 soldiers and police protecting the city, while ISIS forces had only 1500 men. The army was not prepared for the violence ISIS members employed, and some soldiers abandoned their posts and weapons in an attempt to escape the violence. 

(Image via Wikipedia)

The Bay of Pigs

The Bay of Pigs

Exiles of Fidel Castro's Cuban revolution tried to thwart the communist leader with the Bay of Pigs invasion. This operation, which took place in 1961, was a spectacular failure. 

It was particularly embarrassing for the United States, who had covertly funded the failed mission. The Bay of Pigs led to increased tension between the US and Cuba, and solidified Fidel Castro as a powerful military and political figure. 

(Image via Wikipedia)

Operation Barbarossa

Operation Barbarossa

Hitler and the Soviet Union didn’t really get along. He wanted to destroy the Soviet Union no matter what, and that’s why Operation Barbarossa went down. The biggest mistake Hitler made during this particular confrontation was delaying the attack on Moscow. 

This allowed the Soviets time to defend their capital. At the same time, the Russian winter slowed the German advance. The Soviets, who were used to the winter, attacked, and Operation Barbarossa became Hitler’s first defeat.

Bundesarchiv, Bild 101I-009-0882-04 / Schröter / CC-BY-SA 3.0, CC BY-SA 3.0 DE, via Wikimedia Commons

The Charge of the Light Brigade

The Charge of the Light Brigade

The Charge of the Light Brigade was a famous enough battle to warrant a poem from Alfred, Lord Tennyson. Unfortunately, this charge was an unmitigated disaster for the British calvary. 

During the Crimean War,  the Light Brigade was supposed to prevent the Russians from removing guns from captured positions. However, this message was misinterpreted as a command for a full-frontal attack. The Light Brigade followed what they thought was the call to war and experienced severe casualties because of their obedience. 

(Image via Wikipedia)

The Battle of Little Bighorn

The Battle of Little Bighorn

Also known as the Battle of the Greasy Grass, this battle was a mess. General George A. Custer made some decisions that would go down in history as major mistakes. One of which was refusing to accept Gatling guns to aid in the battle. 

Another was him thinking he didn’t need an additional battalion when one had been offered. This overconfidence is what led to the fight being referred to as “Custer’s Last Stand.”

1025wil/CC BY-SA 3.0/Wikimedia Commons

The Battle of Gaugamela

The Battle of Gaugamela

The ancient Persians might have had the Greeks on the ropes a bit, but the battle of Gaugamela was a decisive victory for Alexander the Great and led to the end of the Persian Achaemenid Empire. 

The Greeks were outnumbered by the Persians, but Alexander's military skill proved to be far superior. Strangely, when Persian king Darius was murdered in the aftermath of the battle, Alexander gave him a full burial as a sign of respect to his military enemy. 

(Image via Midjourney)

The Battle of New Orleans

The Battle of New Orleans

The British definitely lost the Battle of New Orleans, but it was a bit of a blunder for everyone involved. You see, the War of 1812 had ended a full two weeks before the Battle of New Orleans, but neither side hadn't gotten the message yet. 

The British military had more men with more experience in the battle, yet it only took Andrew Jackson and the United States Army a little more than 30 minutes to defeat them. When the dust had settled, the US had lost 60 men, while the British had lost over 2,000. 

New Orleans Museum of Art, Public domain, via Wikimedia Commons

The Fall of Singapore

The Fall of Singapore

The fall of the city of Singapore to Japanese troops during World War II was one of the biggest upsets the British military had ever experienced. The invasion took only a little more than a week and led to the capture of more than 80,000 prisoners of war. 

Winston Churchill himself referred to the fall of Singapore as "the worst disaster and largest capitulation in British history." Close to 10,000 soldiers on both sides died during the conflict. 

(Image via Wikipedia)

The Battle of Chilcheonryang

The Battle of Chilcheonryang

The Battle of Chilcheonryang should have never happened. It began when Koreans received news that Japanese fleets would be crossing the sea. King Seonjo ordered Admiral Yi Sun-sin to attack, but he refused, saying that the information was false. 

He was removed from duty and replaced with Won Gyun. Won Gyun also attempted to refuse the order, but eventually gave in and sailed straight into a trap. A total of 400 men and several vessels were destroyed.

(Image via Wikipedia)

The Battle of Tsushima

The Battle of Tsushima

If your enemy has better communication and better ships, should you attack? That was what the Battle of Tsushima boiled down to. Russia was once considered a top-tier navy, and they wanted to hold onto that title. 

Russia sent a massive fleet to attack the Japanese Navy. The Japanese Navy had faster ships with better guns, and they could communicate through the dense fog that clouded the lights-and-flags communications used by the Russians. Russia lost 28 ships while the Japanese lost three.

(Image via Wikipedia)

Battle of Karánsebes

Battle of Karánsebes

Friendly fire isn’t a unique occurrence, but this bad? The Battle of Karánsebes occurred during the Austro-Turkish war. The Austrian army was scouting for forces when they fired on each other by mistake. 

It isn’t clear how many soldiers were lost, but some records claim up to 10,000 soldiers died that day. Two days after the friendly-fire event, the Ottoman army arrived and easily took Karánsebes.

(Image via Wikipedia)

The Münster Rebellion Cult Rush

The Münster Rebellion Cult Rush

The Münster Rebellion started when the city was seized from Anabaptist rule in 1534. One of the leaders, Jan Matthys, had a vision that he would destroy the invaders if they rode forth on Easter Sunday. 

He managed to round up 12 zealots, and the 13 of them charged into battle against an army of 8,000. Naturally, they were slaughtered. Matthys was dismembered, and his head was stuck on a spike. 

(Fotosearch/Stringer/Archive Photos/Getty Images)

The Musashi’s Existence

The Musashi’s Existence

Bigger, better, stronger, faster! The Musashi was an attempt to make the best battleship out there. Unfortunately, it was too big—and I really mean too big. 

When the ship was ready to launch, the ship needed 570 tons of heavy chains to create dragging resistance that would slow and stop the hull once inside Nagasaki Harbor. Thanks to the chains and the massive hull, the Musashi caused a tsunami that reached almost four feet in height. It flooded homes and capsized small fishing boats.

(Image via Wikipedia)

The Battle of Cajamarca

The Battle of Cajamarca

The Battle of Cajamarca was fought between the Incan Empire and the Spanish. The Inca had strong fortresses that were impregnable, and the landscape was in favor of the defenders, so the Spanish were at a disadvantage. That being said, Atahualpa was overconfident when he announced his convoy would be camping outside of Cajamarca. 

A Spanish conquistador led 180 of his men for an ambush as Atahualpa passed. The group was so densely packed that the Spanish could kill 2,000 and capture another 5,000 Incans, one of which was Atahualpa.

Juan Lepiani, Public domain, via Wikimedia Commons

The Attempted Invasion of Cádiz

The Attempted Invasion of Cádiz

Sir Edward Cecil, a commander, led an expedition into Cádiz. When they arrived, Cecil decided to assault the Spanish city, but it didn’t go well. Several ships escaped, and when Cecil landed his forces, they realized they didn’t have any food or drink. 

So, the commander let his men drink from the wine in the local houses. Naturally, they all got drunk. The Spanish army arrived not too long after, and it’s said they were so smashed the Spanish didn’t have to fire a single bullet—all were put to the sword.

(Image via Wikipedia)

The Battle of Gallipoli

The Battle of Gallipoli

The Gallipoli campaign followed Winston Churchill throughout his military career. Churchill believed the Allied forces could destroy the Turkish army if they attacked, and he spearheaded the operation. 

First, the Allied forces tried to attack by the sea, but Turkish fire and mines kept the ships at bay. A land invasion became the new tactic, but this ended with more than 250,000 Allied casualties, 46,000 of which were dead, and an evacuation. 

(Image via Wikipedia)

The Battle of Inchon

The Battle of Inchon

The battle of Inchon was a major conflict in the Korean war, which allowed South Korean and UN soldiers to retake the city of Seoul from the North Koreans. The operation was conducted by US Army General Douglas MacArthur. 

Other military leaders were unsure that the battle would be successful for several reasons, but in the hands of MacArthur, the operation was executed near perfectly--leading to the capture of hundreds of thousands of North Korean soldiers. 

(Image via Wikipedia)

Napoleon's Russian Invasion

Napoleon's Russian Invasion

Napoleon might have been riding high on his military victories up until the invasion of Russia, but that's where things started to go severely downhill for him. He began the invasion with 685,000 men--the largest army Europe had ever seen. However, by the time he retreated, only 27,000 soldiers remained. 

Napoleon didn't anticipate the Russians' scorched earth policy--they burned their villages and crops before his armies had time to destroy them. This meant that there were no supplies for his troops to plunder, which led to serious issues with their rations. 

Illarion Mikhailovich Pryanishnikov, Public Domain, Wikimedia Commons

The Battle of Marathon

The Battle of Marathon

The Greeks and Persians were battle for world dominance during the ancient Greco-Persian wars. The Battle of Marathon proved to be a decisive and embarrassing loss for the Persian army. 

Despite Spartans being primarily thought of as the military might of Greece, the Persian invasion at Marathon was stopped by Athenians and their allies--and they did it with fewer men than the Persians!

Georges Rochegrosse, Public domain, via Wikimedia Commons

The Battle of Actium

The Battle of Actium

The battle of Actium had it all--Cleopatra, Mark Antony, a soon-to-be Augustus Ceasar. While Augustus (then known as Octavian) and Mark Antony were technically defending different parts of Rome against Egypt, there was the whole Cleopatra debacle that basically made it Octavian against Antony, Cleopatra, and Egypt. 

When all was said and done, Octavian was the only one who had any success. He managed to become the first Emporer of Rome, while Cleopatra and Antony died by their own hands. 

(Image via Wikipedia)

The Battle of Trenton

The Battle of Trenton

The battle of Trenton is an iconic Revolutionary War battle for a few reasons. For one, it's where we get the iconic scene of Washington crossing the Delaware. But it was also a major upset for British troops. 

While Washington went into the battle with 3,000 fewer soldiers than he had planned, he still managed a decisive victory over the British with minimal casualties. This battle raised morale for the war among Americans, who up until this point, had seen it as a bloody failure. 

Marion Doss/Washington at the Battle of Trenton/CC BY-SA 2.0/Flickr

The Battle of Warsaw

The Battle of Warsaw

During the 1920s Battle of Warsaw, Vladimir Lenin and his Soviet troops suffered a stunning defeat at the hands of the Polish during the Polish-Soviet War. Up until this point, things weren't looking good for Poland, and many citizens though a defeat was near. 

However, Polish troops stunned the Soviets with a defeat that saw almost twice as many Soviet deaths as Polish deaths.  This battle turned the war around for Poland and eventually helped them secure their independence. 

(Image via Wikipedia)

Operation Compass

Operation Compass

During World War II, Italian troops were trying to gain a foothold into British-controlled Egypt. However, a surprise attack by the British caused Italian troops to fall into disorganization and eventually defeat in the region. 

Italian troops saw almost five times as many casualties as the British during the operation and suffered major weapons losses as well. 

(Image via Wikipedia)