It was Prussian philosopher and military theorist Carl von Clausewitz who said, “the culminating point of victory” is when an army has achieved its maximum possible gains relative to its political aims and the resources available. Everything that comes after that point is unnecessary and runs the risk of incurring a devastating, strategic loss.
It was Chinese philosopher and general Sun Tzu who said the first essential to victory is knowing when to fight and when not to fight. The second essential is knowing what to do when encountering an inferior force.
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It was American philosopher and “The Gambler” Kenny Rogers who said, “you got to know when to hold ’em, know when to fold ’em, know when to walk away, and know when to run.”
There have been a lot of amazing upsets in military history, but these five losses were especially humiliating because they came at the hands of an ideological or geopolitical rival or just turned the bigger country’s military into a joke.
Arab Allies vs. Israel in the Yom Kippur War (1973)
Israel’s Arab neighbors, taking a page from Israel’s playbook, launched an all-out surprise attack on Israeli positions during the Jewish day of Atonement—the holiest day of the year in Judaism. Since it was also Ramadan, a holy month for Muslims, it was the most unlikely time to launch an attack.
Syria, Egypt, Jordan, Iraq, Saudi Arabia, Libya, Tunisia, Algeria, Morocco, and even Cuba sent troops to fight the Israelis, effectively fielding three times as many soldiers and twice as many tanks and artillery pieces, all armed with the latest Soviet weapons. So, naturally, they crushed the IDF—right? Wrong.
Within a week, Israel’s artillery was shelling parts of Damascus. By the time the UN brokered a ceasefire (19 days later), the IDF was 99km from Cairo.
India vs. Pakistan at the Battle of Longewala (1971)
In 1971, Pakistan also tried to take a page from the Israeli playbook, launching an all-out surprise attack on India. They moved 2,000 troops, a mobile infantry brigade, and 45 tanks to secure an Indian border post at Longewala. Unfortunately for the Pakistanis, there were 120 Indians at Longewala who would have none of it. They had one recoilless rifle and strike aircraft that couldn’t fly at night.
For hours, Pakistani artillery pummeled the Indians as tanks and infantry advanced. But the recoilless rifle was the perfect weapon against the T-59 tanks Pakistan was fielding—it turned the thin armor into Swiss cheese. They made easy targets, too, often getting stuck in the soft sand at the border post.
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The advancing infantry got caught up in barbed wire and, thinking they’d walked into a minefield in the dark, flipped out. They waited two hours for minesweepers to clear the field of mines that didn’t exist. By that time, air support was on the way and the Pakistanis were lit up in full retreat.
Soviet Union vs. Finland in The Winter War (1939)
Comrade Stalin was feeling pretty good about his chances of occupying Finland at the end of 1939. All the other dictators were invading smaller neighbors, so why not him? Well, the “why not” is the Finnish Army who really, really hated the Red Army. So, despite being outnumbered and facing down thousands of tanks with their paltry 32, the Finns went to work.
Most importantly, the Finns were ready to fight in waist-deep snow and freezing temperatures, thanks in part to their ski troops, while the Russians, surprisingly, were not. Rather than use good equipment with superior tactics, Stalin threw thousands of troops at the Finns—who promptly killed as many as they could. When all was said and done, the Soviets took three times as many casualties as Finland and only “won” the war because they forced territorial concessions.
When World War II broke out, Finland immediately sided with Germany, invaded those concessions and inflicted another 305,000 deaths upon the Red Army.
Han Xin vs. Zhao Armies at the Battle of Jingxing (205 B.C.E.)
What happens when you put 30,000 troops against a force of 200,000? It should be a total rout. Spoiler alert: It wasn’t.
Sun Tzu’s fourth essential for victory is,
“He will win who, prepared himself, waits to take the enemy unprepared.”
In this case, Han Xin prepared himself. The night before the battle, he sent 2,000 men, each carrying a red Han Xin battle flag, to the rear of the Zhao Army’s camp. Their orders were to occupy the camp as soon as the Zhao pressed their attack.
Xin also dug earthworks on the “wrong” side of a river, putting his back up against the natural feature. The position gave his men fortifications, but also left them no retreat. He marched his army out to meet the Zhao forces. When the fighting began, the Han forces feinted back to the earthworks. With no retreat, they fought like madmen.
Seeing that they weren’t going to take those fortifications right away, the Zhao called for a temporary fallback to regroup. When the Zhao Army saw the thousands of battle flags in their camp, they thought they were being flanked from the rear and promptly fell apart. The Han slaughtered 150,000 Zhao soldiers.
Romans vs. Parthians at the Battle of Carrhae (53 B.C.E.)
A wealthy, young Roman politician named Crassus allied himself with two of the biggest Roman military leaders—perhaps two of the biggest of all time: Julius Caesar, who needs no introduction, and Pompey the Great, who really earned that title. Not content with being just a political ally, Crassus wanted to make a name for himself militarily as well.
He did. But not how he expected he would.
Crassus, then Governor of Syria (conquered by Pompey), led an army of 43,000 legionnaires against the Parthian Empire, running them with no food or rest in order to surprise a mounted force of Parthians in the middle of Mesopotamia. He ran into 10,000 horse archers and some 1,000 heavily armored horsemen, called cataphracts. To defend his army, he formed them into a hollow square, the best defense against mounted units at the time.
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Well, after a few hours of raining arrows on the Romans, the Parthians broke and ran, but it was a feint. As a part of the Roman Army broke off to pursue them, the Parthians (again) shot them with arrows. When the Romans were far enough away from the main force, the cataphracts slaughtered them.
When night fell, Crassus retreated to the nearby town of Carrhae. Parthians killed all the stragglers then cut off Crassus’s head during the next day’s “peace negotiation.”
This loss is particularly humiliating due to the fact that we still reference this battle to this day, with terms like “crass stupidity” and “parting shot.”
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Featured photo of Finnish soldiers manning a heavy machine gun during the Winter War: Wikimedia Commons