How to Win a Fight You Should Lose: The Art of Asymmetric Warfare

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Throughout history, poorer, weaker or outnumbered forces have beaten stronger ones by refusing the fight the stronger side was built for, using terrain, technology, doctrine and, most often, making a decision on what they were willing to give up in exchange for a chance

Everyone loves a good underdog story, and military history provides some of the best of them.

Some of them sound stranger than fiction, but what’s fascinating is that the winning side made the same 4 choices almost every time:

1. They refused to fight the war the other side showed up for: Every big army has a kind of battle it is built to win, and in every one of these stories the underdog simply would not give them that battle.
2. They picked the environment: They went looking for a place where being bigger stopped helping, whether that was a 50-foot pass, a strait with a violent tide, a muddy field or a frozen forest with one road through it. In all of those places the larger army could only fight with whatever fit in front, so the numbers behind it were just waiting their turn.
3. They showed up with something the other side had not planned for: War wagons, cannon that could hit from a distance, the longbow, an 18-foot pike, soldiers on skis, or even “turtle ships”. None of it was a secret, and in most cases, the stronger side had seen it before and decided it was not worth taking seriously.
4. They decided ahead of time what they were willing to lose: A bigger army wins by taking things, so the underdog had to be honest about which things it could live without. Hannibal gave up the middle of his own line, the Afghans gave up their capital twice, Haiti burned its own farmland and Finland gave up a tenth of its land to stay a country.

Here’s a running list of battles that take up more of my mindshare than I care to admit:

1. Jan Žižka (Hussite Wars, Bohemia, 1420s): A blind Czech general beat Europe’s professional knights using farmers and farm carts. In 1420, he had roughly 400 people and 12 wagons against 2,000 armored cavalry, and over the next 11 years, 5 separate papal crusades marched into Bohemia and all 5 lost and went home. His answer to heavy cavalry was to chain the carts into a rolling fortress and fill them with crossbowmen and small cannon, which left the most feared weapon system in Europe with nothing to charge at since you can’t lance a wall.
2. Yi Sun-sin (Korea, 1597): By the autumn of 1597, the entire Korean navy was 13 ships, and Japan sent 133 warships to finish it off. Yi sank or crippled 31 of them, did not lose a single hull, and sent the Japanese fleet back home. He fought in a strait where the tide reverses hard enough to shove a fleet sideways, and timed the battle so that the Japanese could only enter a few ships at a time, destroying them at a range their boarding tactics had no answer for.
3. Greece vs. Persia (490-479 BCE): Everyone loves to talk about Thermopylae, where 300 Spartans held a pass against a Persian army modern historians put somewhere between 120,000 and 300,000. Why? The pass where the fighting took place was about 50 feet wide, so all those Persians could only ever put a few hundred men into contact at a time. But that war has two better stories nobody tells:
   • Marathon (490 BCE): about 10,000 Athenians attacked a Persian force of roughly 25,000 and walked away having lost 192 men. Persia’s whole advantage was archery, so the Athenians sprinted the last 200 yards to cross the killing zone before the arrows could do their work, then hit men in wicker shields and quilted cloth with a solid line of bronze armor and 8-foot spears.
   • Salamis (480 BCE): Athens had already been burned, and the Greek fleet was the last thing standing between Persia and the rest of Greece: 370 ships against 600 to 800. The Greeks leaked a fake message that they were about to flee, so Persia rowed into a channel too narrow to use its numbers in, where its ships bunched together and got rammed side-on. Persia lost 200 to 300 ships that day.
4. Agincourt (1415): 4 out of every 5 men in the winning English army were archers, which was unconventional but the third time in 70 years that fact had ruined a French army. The English had about 6,000 troops, sick and short of food, against a French force somewhere between 12,000 and 25,000, and by evening, France had lost more men killed and captured than the English had brought to the field. They funneled the French onto a narrow strip of freshly plowed farmland after a night of rain, so that France’s nobility had to walk uphill through mud, in 60 pounds of steel, while longbows worked on them from 200 yards.
5. Hannibal at Cannae (216 BCE): West Point still teaches this battle 2,200 years later, and nobody has improved on it. Hannibal had 50,000 men against 86,000, the largest army Rome had ever put in a field, and by sundown, Rome had lost most of it, along with 80 of its senators. Hannibal pushed his weakest troops forward and let them fold slowly backward, so that the Romans kept advancing into a sack, and then closed his cavalry behind them, leaving an entire army packed too tightly to raise a sword.
6. Finland vs. USSR (Winter War, 1939-40): A country of 3.7 million was invaded by a country of 170 million, and 3 months later it was still a country. Finland defended itself with 32 tanks against roughly 2,500, and 114 aircraft against 3,880. Its ski troops in white camouflage cut the road-bound Soviet columns into isolated pockets and then finished them one at a time. In a single encirclement in January 1940, a Finnish force of 6,000 broke a division of 14,000 and drove off with 43 of its tanks and 71 of its guns.
7. Afghan resistance vs. Britain and the USSR: Two global empires took Kabul easily, 140 years apart, and both left with nothing. Britain marched about 16,000 people out of the city in January 1842, and only one European officer reached the next garrison alive; the Soviets pushed 620,000 personnel through over 9 years, and withdrew in 1989 having changed nothing. The reason is that Afghanistan gives an invader nothing worth capturing: power lives in the valleys rather than the capital, so no one’s surrender binds anybody else, and the terrain squeezes a modern army onto a handful of roads, where a column stretched over miles gets picked apart by men who then go home for dinner.
8. The American Revolution: A string of farm colonies on the edge of the map beat the most powerful empire in the world. They never had more than 48,000 men under arms at once, and their navy peaked at 31 vessels against a Royal Navy that grew to 478 ships. They won by refusing to give Britain the war it was built for, keeping an army alive rather than risking it, and letting militia fight British columns in the woods between towns until an empire 3,000 miles from home ran out of reasons to keep paying.
9. Toussaint Louverture and the Haitian Revolution (1791-1804): Haiti is the only country on earth whose independence was won by an uprising of the enslaved. Napoleon sent 31,000 men, under his own brother-in-law, to take one island back, and roughly 7,000 of them came home. The Haitians gave up ground deliberately, pulled into the mountains, burned what they left behind and waited for summer, when yellow fever emptied the French camps for them (it took the brother-in-law too).
10. Swiss pikemen vs. Habsburg and Burgundian knights: Europe’s poorest mountain farmers in Switzerland made themselves into its most expensive soldiers by beating the continent’s richest army twice in a single year. In 1476, that army lost between 6,000 and 10,000 men to a Swiss force that buried 410 of its own. A block of 18-foot pikes moving at a jog cannot be charged by cavalry, and once that became obvious, kings stopped fighting the Swiss and found it cheaper to just hire them.

Every advantage has an expiration date

The Swiss are the right place to end, because their story includes the most important lesson. For 40 years nobody in Europe could beat the Swiss pikemen, until the French figured it out in 1515 with massed cannon and defeated thousands of them in a single afternoon. Switzerland made peace with France the next year and has stayed out of other people’s wars ever since, so 500 years of Swiss neutrality traces back to the day its edge stopped working.

Every edge on this list was a window. Environments get scouted, tools get copied, tactics get drilled against, and sooner or later, the stronger side takes you seriously. The 4th choice is the only one that does not expire, because knowing what you are willing to lose is a decision about who you are rather than how you fight. The Swiss worked out the final version of that choice 500 years ago: sometimes the thing you give up is being in the fight at all.

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