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10 of the Worst Military Decisions in History

Everybody makes mistakes, and to err is only human. When a modern civilian errs at work, the results can end badly. Invoices fail to go out, reports don’t get filed, and sometimes a company goes under because of bad planning or bad decision making near the top. When a military leader fails at his job, on the other hand, the results range from mass slaughter to the fall of a kingdom. It can hurt the world. That’s why it’s worth having a look at 10 of the worst military decisions in recorded history, in case you someday wind up in command of a massive military operation yourself.

Invading Russia – Ever, For Any Reason

Russian flag

Parker Brothers came out with its first edition of Risk in 1959, which in the event was far too late to help the various huge armies that have boldly invaded, and then meekly died in, the vast Russian countryside. Invasions of Russia have historically gone something like this: Western European leader gets the idea of taking over Russia. The said leader knows it’s going to be a big deal, so he drafts half his country’s male population and plunges into the void. The Russians, always taken by surprise, despite how often this has happened to them, fall back for thousands of miles and burn every blade of grass on the way. Deprived of food, exhausted from marching, and stuck in the frozen mud, the invader’s army stalls and eventually collapses in the winter. This is followed by a massive Russian army rolling over them and sending the unlucky survivors to slave away at labor camps somewhere. Every. Single. Time.

The first invaders to get this treatment were the Teutonic Knights in the 13th century. Fresh from genociding the native Prussian tribesmen, the Teutonic Knights were riding high. Seeing more primitive savages to their east, the Order enlisted Sweden as an ally, which was a bigger deal back then than it would be now, and charged toward what is now Saint Petersburg. Along the way, in 1240, they bumped into Alexander, Prince of Novgorod, who drew them out onto a frozen lake and no doubt laughed himself silly when they plunged through the ice and drowned.

Almost 600 years later, Napoleon Bonaparte tried his luck in Russia and got as far as Moscow, before winter set in, and the Russians counterattacked. Months later, the 600,000-strong Grande Armee was Fin et le Mort, and Napoleon was on his way to Elba. A century after that, the Germans tried occupying Russian Poland, which was the bloodiest front of WWI. Twenty years after that, the Nazis tried the same trick in a campaign that began with lightning victories and ended, four years later, with Red Army soldiers redefining the German gene pool in their successful passage through Prussia.

The French Attack at Agincourt

The French Attack at Agincourt

As noted above, we all make mistakes. It would be wrong to blame a conscientious leader for goofing up one time, but to make the exact same mistake twice, in two different battles of the same war, in events so far apart in time that the men killed in mistake #2 might be the grandchildren of the men killed in mistake #1, in a bit much to forgive. Such was the worse case of the French at the 1415 battle of Agincourt. The story of Agincourt begins 69 years earlier, at the Battle of Crecy. There, French heavy cavalry dismounted (good war horses were too expensive to risk in combat) and marched straight at the side that history calls English, though they were mostly from Aquitaine and Wales. The Welsh had brought war bows and bodkin arrows that sailed through chain mail

The story of Agincourt begins 69 years earlier, at the Battle of Crecy. There, French heavy cavalry dismounted (good war horses were too expensive to risk in combat) and marched straight at the side that history calls English, though they were mostly from Aquitaine and Wales. The Welsh had brought war bows and bodkin arrows that sailed through chain mail armor, and so the battle went as badly as you’d expect for the French attackers.

What makes a mistake at Agincourt so infuriating is that almost seven decades later on, when you’d think the lessons of Crecy would have been thoroughly learned and digested by two generations of French knights, they went and did the same dumb thing all over again. Once again, at Agincourt, the French dismounted and marched across a muddy field chosen by the English (for real English this time, plus more Welsh archers). Again they got hit with a blizzard of arrows, and still, they fell by the hundreds until the whole tremendous force was beaten. Who could have seen that coming?

Dishonorable Mention: Winston Churchill

Winston Churchill

Speaking of not learning from your mistakes, the sad military career of Winston Churchill stands as a testament to savvy politics overcoming good leadership that modern mediocrities can learn a lot from. Churchill’s hands-on military experience at the beginning of his career consisted mainly of attending some battles in the Boer War as a journalist and being the son of Lord Randolph Churchill, scion of a distinguished military line. This was apparently enough to get him appointed First Lord of the Admiralty, where he was a regular cauldron of ideas during the early years of World War I.

One of those ideas was to invade the “soft underbelly of Europe,” which in this war took the form of attacking the Germans’ Turkish allies on the Gallipoli Peninsula, a few days’ marches from their capital city and on the far side of the Mediterranean Sea from the British Navy. After the epic slaughter of Australians and Kiwis there, Churchill was forced out of government for a time.

He came back, however, and continued his obsession with soft underbellies as Prime Minister during World War II. Instead of Gallipoli, this time Churchill devised an invasion of, in order, Sicily, Southern Italy, and the South of France. These went, in order: Bloody, disastrous, and unnecessary, given the parallel landing at Normandy. Nobody seems to have totaled up the number of Commonwealth, British, and American soldiers who died making a point that Churchill never learned, but at least there was never a World War III, which would no doubt have seen British forces invading Portugal.

The Alamo, Remember?

Battle of the Alamo

Not all bonehead decisions result in defeat. Sometimes, when the army making all the mistakes is present with overwhelming force, they can’t help but win by sheer volume and inertia. This is dangerous because victory sometimes shields stupidity and leaves the offending leader with a frankly unearned halo. Such was the case in the infamous 1836 siege of the Alamo.

The problem here was not one of execution, though Santa Anna did order the first attack before his heavy batteries had caught up with his infantry and the initial charge neglected to bring ladders along to scale the walls. Instead, the issue was strategic, as in: why attack the Alamo at all?

What made the Alamo important in 1836 was that it lay on the road between the Mexican Army and Austin, where Texas’ rebellious founders were drafting a declaration of independence. Santa Anna’s imperative was to get from San Antonio to Austin before the final draft could be issued, which would preserve the Mexican line that Texas was just a rebelling province, not a free country. Instead of just going the hell around the Alamo, Santa Anna chose to strike the irrelevant outpost full of hungover Texans. He won, but the days-long delay bought all the time Texas needed to proofread and adopt the declaration. War followed (eventually), which saw Santa Anna go into exile while US Marines danced on his roof in Mexico City.

The Road to Stalingrad

Battle of Stalingrad

The Soviet Front was the most significant war humans had ever fought, so it deserves a second mention here. One decision, in particular, stands out as the moment when Heinz Guderian later claimed he was sure the war would be lost: Hitler’s insane decision to reinforce the southern front in 1942. As soon as Hitler committed himself to this brilliant idea, which came to him as a flash of inspiration that his generals would never talk him out of, the German Army was forced into a series of horrible decisions that would culminate by the end of the year at Stalingrad. The winter of 1941-42 was hard for the Germans, who had planned to kick over Stalin’s 11-time-zone-having ass in a few months at most. When that didn’t work, the spring offensive targeted Moscow, which was more than just the capital, it was the biggest logistics hub in the Soviet Union and a significant key to continued Soviet resistance. Knocking out Moscow would have crippled the Soviets’ ability to shift forces north and south along the line, giving a perhaps decisive advantage to the Germans.

The winter of 1941-42 was hard for the Germans, who had planned to kick over Stalin’s 11-time-zone-having ass in a few months at most. When that didn’t work, the spring offensive targeted Moscow, which was more than just the capital, it was the biggest logistics hub in the Soviet Union and a significant key to continued Soviet resistance. Knocking out Moscow would have crippled the Soviets’ ability to shift forces north and south along the line, giving a perhaps decisive advantage to the Germans.

Instead of doing that, Hitler decided – perhaps after being prompted by invisible time police from the future – to shift an entire corps command south to reinforce the drive into the Baku oil fields. By robbing his center of its strategic reserve, Hitler all but guaranteed that Army Group Center was going to stall somewhere on the road to Moscow, as well as condemning the entire Sixth Army to a frozen grave in Stalingrad six months later.

Aethelred the Unready Gave Vikings the Benefit of the Doubt

“Unready” is derived from the Old English “Unraed,” meaning “foolish” or “ill-advised,” which probably fit no leader better than Aethelred. A British king in the late 10th century, Aethelred started his career by unwisely facing off against an invading Danish army at Maldon. There, the lay of the battlefield saw the entire Viking force stranded on a tidal causeway and able to attack the English only by twos and threes, which made defending the spit embarrassingly easy. Capitalizing on this, the Danish commander called to Aethelred that it was unfair and unsporting to maintain this advantage and that a real man would face them in the open field.

True to his name, King Unwise pulled his army back a bit and let the Vikings land properly, at which point they smashed his force. Knowing a useful idiot when they saw one, the Danes allowed Aethelred to live, at the cost of an annual tribute, called the Danegeld. Little did Aethelred suspect that, when once you’ve paid the Danegeld, you’ll never be quit of the Dane. When this dawned on him in 1002, Aethelred ordered a massacre of Danish settlers. This went down as well as you’d expect with Vikings, who invaded (under Swen Forkbeard) and drove Aethelred into exile in Normandy. He came back after Swen’s death, only to again piss off the Danes and get another invasion in his rear area in 1016, which put an end to His Majesty the Stupid for good.

Don’t Snub the Mongols

Mongols Genghis Khan

Genghis Khan had a straightforward approach to foreign policy: non-Mongolian tribes got one warning, usually in the form of a letter demanding tribute, followed by genocide if the answer was no. For some bizarre reason, nobody in 13th-century Eurasia ever took him at his word, which is why the Great Khan found himself moving from one newly created desert to another all his life. The Muslim Caliph, for instance, got a polite invitation (from the Khan’s successor, Subotai) to cough up his treasury in 1234. When the Caliph replied with a letter of his own, which effectively called Subotai “boy” and boasted of all the believers who would fight for Islam, the Mongols swept through Mesopotamia and made it the barren paradise it is today. The Caliph himself seems to have been rolled up in a carpet and kicked to death by ponies.

The next such mistake was made by the Princes of Kiev and Novgorod, when their hated rivals, the Polovtsi, appeared at their courts and begged for help against the Mongols. The Mongols sent emissaries of their own, who essentially offered free peace in exchange for the Princes turning a blind eye to “our slaves and grooms the Polovtsi.” Instead, the Russians allied and faced off against the Mongol Horde with their new best friends the Polovtsi, which is why the current population of Russia is far lower than that of China, a country that was significantly less stupid when the Mongols came for them.

Japan Wastes Its Navy on a Hunch

Japan Navy

The received wisdom on WWII in the Pacific was that, but for the grace of God, the Japanese might have won it. Midway, in particular, was allegedly a turning point in the fight, when good codebreaking, good fighting, and plain good luck delivered an unlikely victory to the US Navy in the face of overwhelming odds. The Japanese were never going to win that battle and losing it may have shaved a year off of the final victory.

When US code breakers picked up encrypted Japanese messages about the impending invasion of a place they called “AF,” they knew Midway was one of a few spots that could be. Through a clever ruse, the Navy tricked the Japanese into identifying AF in a communique, which gave the Americans a decisive edge in the fight. What’s overlooked is that, even if those dispatches had never been intercepted, the battle of Midway would never have gone well for Japan.

The whole Japanese plan was to attack Midway, which they thought would force the Americans to charge out and fight at a disadvantage. As Admiral Nimitz would later admit, if the Japanese plan had come off, the US forces would probably have just laid siege to the island from a distance, rather than trying to storm the “unsinkable aircraft carrier” Midway. In the event, the Japanese Navy lost the element of surprise, got caught in the open, and was savaged, losing four carriers at the very moment the US war effort had 11 of its capital ships in various stages of completion. Gambling on Midway doomed the Japanese war effort for good.

People Keep Invading Afghanistan


Afghanistan is called the graveyard of empires for nothing, and the native Pushtun people have done everything that they could to earn that reputation for thousands of years. When Alexander the Great invaded the western part of Darius III’s Persian Empire, many of the Persian forces were unavailable to deal with the incursion because they were tied up crushing a revolt in what is now Afghanistan. After the invasion came off, and Darius had been killed by his general, Alexander decided to invade the same no-go zone as Darius had. The Pushtun hit Alexander with an arrow in the lung, the wound that would eventually kill him at 32.

Centuries later, empires still couldn’t keep their hands off of Afghanistan, which – to be clear – has never had a single resource any major empire needs. The British invaded three times, beginning in 1842 with a force of 40,000 men. When the three survivors staggered back into India in 1845, the British decided to make the place a buffer zone against the Russians.

Speaking of Russians, they invaded too, in 1979. Because they were communists, this was officially not an imperialist invasion, but a fraternal socialist helping hand to the Najibullah regime, which was barely clinging to power in Kabul. Ten years later, as the Russians were fleeing what would become the Taliban to find their own country ruined, Afghanistan settled back into its customary misery for a relatively quiet decade. The United States decided to invade in 2001, which eventually turned into America’s longest war and sank a sizable fraction of the national treasure into an unproductive hole. These days, China seems to have designs on opening a trade route to the west that will cut through a bit of Afghanistan.

Don’t do it, China. You’ll be sorry.

Operation Eagle Claw

Operation Eagle Claw

Operation Eagle Claw was the American special forces raid into Iran to free the hostages in 1980. It was such a complicated plan, with so many unconnected and unnecessary complications and extra steps, that even its commander gave the mission less than a 1-percent chance of success. Unsurprisingly, it ended in tears and collapsing scenery, and with it the end of Jimmy Carter’s political career.

Eagle Claw was supposed to be a super-cool Entebbe-style raid by American forces to free the 52 embassy hostages who were at that time being held somewhere in Tehran. It was doomed from the start, if only because every branch of the service had to be included because of inter-service rivalry, whether they were the best force for the job or not. See if you can spot the flaw in this plan:

  • CIA agents inside Iran would covertly set up fueling stations in the desert west of Tehran
  • Air Force helicopters, operating from Marine Corps assault ships, would fly to the first airbase, then refuel and move to the second base, where…
  • More CIA agents would have some stolen trucks to drive the Delta Force commandos into Tehran, where they would chill out for 24 hours
  • Raid
  • Delta, joined by Airborne Rangers, would escort the 52 hostages in commandeered vehicles to a third airbase, where helicopters would pick everybody up
  • Victory lap

It was a complicated plan, and every single element had to work correctly or else. Of course, nothing went right from the start, and when a sandstorm blew up, and a helicopter crashed into a refueling chopper, the whole mission had to be scrubbed. “Only” eight Americans lost their lives in this comedy, but America was humiliated, and those hostages stayed put until President Reagan took the oath of office nine months later.

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