Before the battle of Singapore in World War II, the British were pretty sure their stronghold was invincible. To the north of the city were impassable swamps and jungle that no one was crazy enough to try to march an army through. The south was protected by five 15-inch guns (that is, the shells were 15 inches across) that would turn approaching ships into Swiss cheese, and 85,000 British troops to meet anyone who landed.
The British called it the Gibralter in the Far East and their main concern was that it was too untouchable. As one officer in the British army was quoted as saying, "I do hope we are not getting too strong in Malaya because if so the Japanese may never attempt a landing."
The Fatal Flaw:
The whole defense of the city was dependent on the idea that the attack would come from the south sea. After all, you'd never get an army through the jungle to the north. How would you get your heavy artillery or tanks through it? What were they going to do, put their troops on bicycles or something?
Yes. Thousands and thousands of bicycles. The Japanese came pouring through the jungles with alarming speed. The British turned their coastal guns around and bombarded the Japanese attack, but it accomplished nothing. They were designed to punch holes in ships, not repel a gigantic militarized Tour De France.
The Japanese were able to attack several areas of the island from the north. Fearing the speed of the BMX-riding Japanese, the British detached forces to all these places to avoid encirclement, which spread their lines too thin. These lines were soon broken and they were surrounded. By February 15, 1942, the British had no option other than surrender. The 80,000 men became the largest surrender of British personnel in history.
When recounting the Battle of Singapore, One Australian officer stated, "The whole operation seems incredible: 550 miles in 55 days - forced back by a small Japanese army of only two divisions, riding stolen bicycles and without artillery support." Well, damn, when you put it that way...
#1. Chateau Gaillard
During the 13th century, England and France were having one of their many, many wars with each other. To protect his holdings in Normandy, Richard I of England wanted to build the most badass castle imaginable. Six thousand laborers worked for a year to build the fortress. When the castle was completed, Richard called it a "gaillard castle" (translated: "well built"). Yes, Richard sucked at naming things.
The castle presumably rested on "Green Mountain."
It was in the perfect spot, on a high plateau with steep cliffs to the sides and rear. The only approach was by the well-armed front, and that sucked even more: it featured a moat, 30-feet wide and 40-feet deep, with a retractable drawbridge. The whole time you're trying to cross the moat you'd be getting pelted with arrows and barrels full of burning oil. Once you make it across, you're facing walls 10-feet thick.
The Fatal Flaw:
The poop chute.
King Richard was sure he'd never see his castle taken. And he didn't. He died less than a year after it was finished. Richard's brother John became king and made one minor addition: an extra toilet in the chapel. The toilet fed the waste into a chute, which emptied outside the walls.
"It's good, but what if I have to poop in church?" - King John
It seemed like a really specific modification to request but maybe they served nothing but Indian food during the services. Anyway, when Philip II of France heard that John was now King of England, he felt it was time to take the castle. Philip marched his army to the castle and laid siege. The soldiers inside the castle were well equipped, with vast stores of supplies that could hold out for an entire year--easily until long enough for re-enforcements to get there.
After a few attempts at taking the castle failed, Philip sent his soldiers out to find a weakness. One of those soldiers was called Ralph the Snubnose. While examining the castle walls, Ralph noticed the latrine chute. He also noticed it was just wide enough for somebody to crawl through.
Ralph, a braver man than any of us, volunteered. He and a couple of soldiers, climbed up the castle's proverbial large intestine, getting covered in excrement all along the way. Once Ralph and his comrades made it through 30-feet of shit tube and reached the top, they opened the gates for the rest of the army and the castle was taken.
After the castle fell, Philip marched through the rest of Normandy. The military failure of the English forces under King John that started at Chateau Gaillard eventually led to him signing the Magna Carta.
Thanks, poop chute!
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For more battlefield monstrosities, check out The 6 Most Gigantic Everything in the History of War. Or learn about some more mistakes made in the Star Wars universe, in 7 Classic Star Wars Characters Who Totally Dropped the Ball.
And stop by Linkstorm (Updated 08.06.10) to discover the weakness in Brockway's cardboard "fortress." (It's actually his house.)