Running an army is kind of like running a day care, only instead of rattles, the children have bombs and guns. Hey, it may not be easy to win a war, but we should at least expect military leaders to be more adept than some kid playing Starcraft.
The Battle of Verdun 1916
Rather than defeat the French outright, the Chief of the German General Staff decided he'd rather pick away at the French via his artillery. There was only one problem, the battle ended up lasting ten months, costing 800,000 lives and bleeding both countries dry. If General Von Lazy Pants had just beat the crap out of the French like a normal country, the Kaiser might have scored a victory.
Battle of Thermopylae 480 B.C.
While this was a great victory for the Spartans and the Greek City states that united with them, it was a disaster for Xeres I who was on a tear across Asia and Europe up until that point. Although the Greeks had only 300 Spartans, they had a total of about 7000 troops versus Xeres' 2.6 million. Despite the lopsided numbers, the Greeks managed to win the day, eventually leading to the destruction of the Persian army and an awesome movie starring Gerard Butler.
Making Benjamin Franklin Butler a General in the 1860's
The American Civil War had its share of drunks and incompetents, but one of the worst generals to ever put on a uniform was Benjamin Butler. Butler stole silverware from Southern homes, ran New Orleans worse than George W. Bush during Katrina, and never once achieved any of his military objectives. He was so hated in the South, people in New Orleans had chamber pots made with his picture at the bottom.
Defeat of the Spanish Armada 1588
The Spanish had a great fleet and a solid record of victories, but it all went to their heads in 1588 when the Duke of Medina Sidonia decided to invade England. The Spanish had relied on their huge armada ships to win battles, but the English had smaller, more maneuverable ships and crews of soccer hooligans. Once the English figured out how to bob and weave, the armada got its clocked cleaned. That and a combination of bad weather and lack of frittatas led to demoralizing losses for the Spanish.
The Battle of Hattin 1187
When you're marching in a desert being pursued by a foe that knows the desert well, it's probably a bad idea to leave water supplies behind. The Crusaders, led by King Guy of Lusignan, were being pursued by legendary Muslim leader Saladin. Unfortunately, Guy set off in the desert in the middle of the day and Saladin trapped his forces on a plateau with no water. The ensuing desert massacre would remain unmatched until they shot the movie Ishtar there centuries later.
Pickett's Charge 1863
During much of the Civil War, the Confederates were a well-oiled, redneck, military machine and the Union commanders were inept bunglers. But on July 3, 1863, communication broke down amongst the Confederate battalions and almost everything went wrong. The Union Army lost about 1500 men, but that number pales in comparison to the 10,000 Confederate soldiers lost to death, injury and capture.
The Bay of Pigs 1961
Before JFK was elevated to his saint-like presidential status, he had screwed the pooch on a botched invasion of Cuba. Recruiting 1500 exiles, the CIA sent in the force and promised to give them air support. Unfortunately for the invaders, they found out the hard way that presidents sometimes break their promises. The invasion was a disaster and Fidel Castro became so popular, he eventually launched a successful line of T-shirts based on the image of his friend, Che Guevara.
Custer's Last Stand 1876
General Custer underestimated the Native Americans and bit off more than he could chew at the Battle of the Little Big Horn. Custer and his men were completely wiped out and the victorious Native Americans vowed to build casinos everywhere. Although Custer died, soft serve ice cream continues to honor his name to this day.
The Charge of the Light Brigade 1854
One of the most famous military clusterfucks of all time, the Charge of the Light Brigade was like putting your slow cousin in charge of your family's business. During the Battle of Balaclava in the midst of the Crimean War, a British cavalry led by Lord Cardigan, took his fancy sweaters and some 600 men into what would later be referred to as a “Valley of Death". Rather than attack a smaller force, Cardigan misread the orders and attacked the main Russian force. This was kind of like being ordered to rob a liquor store, but instead attempting to rob a machine gun store run by rabid pit bulls.
Napoleon Invades Russia 1812
Napoleon was a great general, but even a great general has an off day. The little Frenchman must have been really off his nut when he decided to invade Russia in the dead of winter. Although Napoleon took Moscow with many losses, he lost more men on the frozen march back to France. In total, half a million soldiers were killed during the entire debacle and many were forced to eat substandard cheese and wine. Napoleon regretted this and his appearance in Bill and Ted's Excellent Adventure. Fortunately, no one would be stupid enough to ever repeat this mistake.
Hitler Invades Russia 1941
Adolf Hitler, never a good student of history, decided to exactly what Napoleon did, only more evil. In a plan called Operation Barbarossa, Hitler betrayed his former ally, Stalin, and invaded with 4.5 million troops. Things actually went worse for Hitler, as he attempted to occupy Russia. That was kind of like sending four cops to occupy all of South Central L.A. Overstretched and pounded by winter, the Nazis were killed, captured or routed by the Commies. Hitler and Stalin never spoke again.
The Marginot Line
Another military disaster involving France, what a shock! In this one, the French has built an “impregnable" line of guns at the end of World War I. They were totally awesome --- Unless your army had a car. When the Nazis invaded, they wisely chose to go around the line through Belgium. The French, having put a lot of their eggs in the Marginot basket, didn't stand much of a chance against the advanced Nazi Panzer Tank.
The Vietnam War
Up until Vietnam, the US had a pretty impressive streak of military wins. In an attempt to keep Commies out of Saigon, the US let itself get sucked into one of the stupidest conflicts in history. Millions of lives were destroyed and hippies ruled the streets for the next decade.
The Soviet Invasion of Afghanistan 1979
Also known as the “Soviet's Vietnam" or the “Big Russian Suck", Leonid Brezhnev got the bright idea to invade Afghanistan one day. After ten years of letting Osama Bin Laden kill their troops, the Russians wised up and left just in time for their entire country to collapse. America won the Cold War shortly thereafter and no one would be stupid enough to ever repeat this mistake again!
The US Invasion of Iraq 2003
Called by retired Lt. General William Odom as the “greatest strategic disaster in United States history", the invasion of Iraq continues to be a long, drawn out occupation that has expanded into Afghanistan and Pakistan. Started by George W. Bush and continued by President Barack Obama, occupying Iraq continues to be about as much fun as paying a guy to kick you in the nads every five minutes.