25 Worst Military Decisions Ever Made

Posted by , Updated on March 21, 2024

Overconfidence, carelessness, and momentary mental breakdowns can have pretty bad consequences in every day life. Imagine for a moment though what sort of catastrophes they can lead to on the battlefield. With millions of lives on the line one little mistake can literally change the world. From Word War II to Thermopylae these are the 25 worst military decisions ever made and how they affected the course of history.

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The Battle of Thermopylae (480 B.C.)


This was the epic battle of 300 Spartans who fought against thousands of Persian troops in a historical event that has gained even more attention from Gerard Butler’s swashbuckling historical movie simply titled 300.  Thermopylae is arguably the most famous battle in European ancient history and has been cited as an example exemplary valor, courage, strategy and heroism.  Although the Greeks lost the battle, it set the stage for them to eventually defeat the Persians and win the war.


The Battle of Carrhae (44 B.C.)


Just because you’re rich and war hungry it doesn’t mean you’ll win all the battles moving forward. General Crassus of Rome should have learned this truth before confidence got the best of him.  The battle of Carrhae was the first battle fought between the Roman and Persian empire resulting in a crushing defeat for the Romans.  In spite of their overwhelming number and heavy infantry the Roman army was outdone by the Parthian cavalry led by Spahbod Surena.


The Battle of the Red Cliffs (208 or 209 A.D.)

red cliffs

Spies have mostly been the trump cards in armed conflicts. You’d be lucky if they’re caught before the damage is done. Chinese warlord Cao Cao found this out the hard way when a spy disguised as an adviser convinced him to chain his ships together to prevent his soldiers from getting seasick. This error eventually contributed to the fall of the Han Dynasty.


The Battle of Hattin (1187)


There’s a couple things that anybody about to wage war in the desert will probably need. One is water and the other is common sense. Unfortunately, King Guy of Lusignan of the Crusaders lacked both and his enemy, the legendary Muslim leader Saladin, knew it. Conveniently, the latter trapped the king’s men on a water-less plateau and the rest is history.


The Defeat of the Spanish Armada (1588)

defeat spanish armada
Like the usual attitude of most notable names in war history, the Duke of Medina was supremely confident that Spain would have England on her knees because of their amazing fleet and long string of victories. Little did the Duke know that their famed armada would be destroyed by the smaller and more maneuverable English ships.

The French Invasion of Russia (1812)

french invasion of russia

Yet another epitome of sheer overconfidence would be Napoleon Bonaparte’s winter invasion of Russia. Not surprisingly the weather took its toll on the French and as they suffered a long and freezing retreat back to their home country.


The Battle of New Orleans – War of 1812 (1812 – 1815)

battle of new orleans

General Edward Pakenham, the commander of English forces in North America made a fateful decision during the battle of New Orleans that his troops should hold their fire just a little longer than what was necessary. At the end of the day, at the age of 36, it cost him his life.


The Battle of Waterloo – Last Napoleonic War (1815)


In the middle of a battle, Napoleon took the time to nurse his illness and delegated the responsibility of winning the battle to Marshal Michel Ney. Unfortunately for Ney after the British where able to stop his first attack, it wasn’t enough to convince him that his strategies needed some adjustment.  He proceeded to launch the same attack which was countered again by the British. In fact, he repeated the same attack numerous times and in no small way contributed to the high French casualty count.


The Battle of San Jacinto – Texas Revolution (1835-1836)

san jacinto

In an almost unbearably poor lapse in judgement General Antonia Lopez de Santa Anna of Mexico vastly outnumber the 910 Texans he was fighting, but in the end suffered massive defeat. Why? All because the general ordered his men to take a siesta. It was a costly nap as he lost 630 men while the Texans only lost 9.


The Battles led by General Gideon Pillow – Mexican American War (1846-1848), The American Civil War (1861-1865)

General Gideon Pillow

It can be difficult to elbow your way through the ranks to become general.  Then again  maybe you don’t have to, that is if your college friend is the President of the United States of America.  Such was the infamous case of General Gideon Pillow whose several mishaps in battles during the Mexican American War and the American Civil War resulted in thousands of lives being lost. To make matters worse, at one point he was even found hiding behind a tree to avoid leading his men into battle.


The Charge of the Light Brigade (1854)

charge of the light brigade

Miscommunication can lead to disastrous results.  Such was the case for Lord Cardigan of the British Calvary who misread an order and instead of fighting an enemy’s smaller unit,  ended up going head to head with the main Russian force.  So bad was this incident that similar situations are now referred to as the “Valley of Death”. If only Lord Cardigan had read that order correctly…


The Leadership of General Benjamin Franklin Butler (1860′s)


During the American Civil War, he served as a major general in the Union Army. His policies regarding slaves as contraband so they could have freedom, his administration of occupied New Orleans, his ineffectual leadership in the Bermuda Hundred Campaign, and the fiasco of Fort Fisher rank him as one of the most controversial and ineffectual political generals of the war.


The Battle of Antietam – The American Civil War (1861-1865)

battle of antietam

Although General Ambrose Burnside knew that the lives of his 12,000 men would be in severe danger were they to cross the river without a forge, he made the call to move forward anyway. If only he would have looked just a little longer he would have noticed that a forge actually did exist in the area.


The Battle of Chancellorsville – The American Civil War (1861-1865)


Is there a greater advantage if you were looking up at the enemy from the bottom of a hill or looking down at the enemy from the top?  Although most people would choose to be on the higher ground General Joseph Hooker went against common wisdom and it ended up costing him dearly. Following the battle Abraham Lincoln relieved him of command.


Pickett’s Charge (1863)

Pickett's Charge

Although there were some controversies looming as to why General Robert Lee ordered the charge; one thing’s for sure,  everything went really wrong.  By the end of the confusion and chaos, leaders would be pointing fingers at each other but the lives of the 10,000 men who were lost that day because of their miscommunication would never be retrieved.


The Battle of the Little Big Horn – The Great Sioux War (1876)

Little Bighorn

General George A. Custer  made some crucial errors in the battle of Little Big Horn.  One of the most blatant errors was his refusal to accept a battery of  Gatling guns while another error was his refusal to accept General Terry’s offer of an additional battalion from the 2nd cavalry. Apparently overconfidence is a popular trait among military leaders.


The Battle of the Somme – World War I (1914-1918)


Field Marshal Douglas Haig of the British Expeditionary Force has been criticized, along with several French commanders, of grossly mishandling the battlefield. At the end of the three day offensive over 630,000 British and French troops lost their lives fighting German forces.


The Battle of Verdun (1916)


German General Staff made the mistake of trying to defeat the French through a persistent campaign of heavy shelling. Unfortunately, the French were very resilient and they managed to adapt their tactics to eventually turn the battle in the their favor.


The Maginot Line (1935-1969)

Maginot Line

This solid line of concrete fortifications constructed by France shortly after World War I was meant to prevent invasions, particularly from Germany or Italy. Unfortunately for France they had failed to build the wall along the border with Belgium which allowed the Germans to flank it in World War II and conquer France within roughly 6 weeks.


Operation Market Garden – World War II (1939-1945)

Operation Market Garden

This operation was the biggest airborne operation in history but was an unsuccessful move by the Allied forces. In an attempt to route the Germans and capture several bridges things seemed to be going well at first but they went south when General Bernard Montgomery failed to secure a critical point. The British did not expect as much resistance as they faced and ended up being pushed back. The failures here extinguished the hopes of ending the war by Christmas of 1944.


Operation Barbarossa – World War II (1939-1945)

Operation Barbarossa

In all of history there have been few tactical decisions so costly as Hitler’s move to split his army and begin an invasion of the Soviet Union. Not only did it leave to Germany’s eventual defeat but it led to some of the bloodiest and most violent fighting of the war.


The Vietnam War – 1955 to 1976

The Vietnam War

In this sensational war between North Vietnam; who was backed up by its communist allies, and South Vietnam; supported by the United States and the anti-communist allies, the US and its allies ended up backing out due to multiple political, social, and military issues plaquing the war from the start. By the time the last American soldier left Vietnamese soil millions of lives had been lost due to poor decision making and resource management.


The Bay of Pigs (1961)

The Bay of Pigs

Used throughout Latin America as an example of the failure of American imperialism, the Bay of Pigs invasion involved roughly 1400 paramilitary troops backed by the CIA landing in Cuba and attempting an overthrow of Fidel Castro’s government. The invasion failed and most of the troops were interrogated before being shipped off to the United States.


The Soviet Invasion of Afghanistan (1979)

The Soviet Invasion of Afghanistan

After millions of injuries and casualties; the “Soviet Union’s Vietnam War” or the “Big Russian Suck” which lasted for 10 years finally came to a close. This decade long bloodbath was caused by the Soviets supporting the Afghan communist government to defeat the Mujahideen; an Islamic group composed of tribal and urban insurgency groups. Because the United States backed up of the latter, the war endured for so long without any progress in freeing the Afghan government from the insurgents. The massive losses caused the Soviets to finally agree to withdraw and Afghanistan went back to it’s original state.


The Alamo (February 1836)

The Alamo

When Mexican General Santa Anna was on his way through Texas to squash a rebellion he decided to make a stop at the Alamo and teach it a lesson. Although he won that battle, his unnecessary detour end up costing him the war as Texas troops had time to assemble. Several days later Santa Anna suffered defeat and the Republic of Texas was born.