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 to me 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. The Hussite Wars (1420s, Jan Žižka): I can’t believe this isn’t a movie yet. General Žižka of the modern day Czech Republic was blind in one eye when the wars started, took a crossbow bolt in the other one at Rábí in 1421, and commanded every campaign after that completely blind without ever losing a battle with his army of literal farmers. At Sudoměř in March 1420, he had roughly 400 farmers and 12 wagons in front of 2,000 armored cavalry, and his answer was to chain the carts wheel to wheel into a fortress that could move and fill them with crossbowmen, handgunners and small cannon. His theory was that knights existed to charge, but you can’t charge a wall. He essentially invented the modern-day tank and with that strategy, he remained undefeated.
2. The Imjin War (1597, Yi Sun-sin): Three months before one of the most lopsided naval victories ever recorded, the Korean government had Admiral Yi Sun-sin arrested, tortured and demoted to common soldier on the word of a Japanese double agent. His replacement lost 166 ships in a single night, so the court gave Yi back his rank and whatever was left of the navy, which was 13 ships. Japan sent 133 warships to finish the job. He fought them in a strait where the tide reverses hard enough to shove a fleet sideways and timed the battle so they could only enter a few hulls at a time, and he sank or crippled 31 of them without losing a single one of his own.
3. Greece vs. Persia (490-479 BCE): Everyone loves to talk about Thermopylae, where 300 Spartans and about 6,700 other Greeks nobody ever names held a pass against a Persian army modern historians put somewhere between 120,000 and 300,000. Why did it work? 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 I think that war has two better stories that 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 get inside the arrow landing zone before the arrows could do their work.
   • 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): The English brought about 6,000 men, most of them sick, and 4 out of every 5 were archers. They then funneled 12,000 to 25,000 Frenchmen onto a narrow strip of freshly plowed farmland after a night of rain, so the nobility of France had to walk uphill through mud in 60 pounds of steel while the longbows worked on them from 200 yards.
5. Cannae (216 BCE, Hannibal): West Point still teaches this one 2,200 years later. He pushed his weakest troops forward and let them fold slowly backward so the Romans kept advancing into a sack, then closed his cavalry behind them and left the largest army Rome had ever put in a field packed too tightly to raise a sword. Rome lost 80 of its senators in an afternoon.
6. Korea vs. Sui China (612 CE, Eulji Mundeok): I had never heard of this one until recently, but an interesting lesson on taking advantage of bureaucracy. China sent 305,000 men to take the Korean capital against an army of 10,000 to 30,000. The result? 2,700 of them came home, and the dynasty that sent them was gone within 6 years. How? They mostly refused to fight, and their best trick came out of the enemy’s own rulebook: the Sui emperor did not trust his generals, so no surrender could be accepted without his personal approval, which meant the Koreans could offer to surrender every time a fortress wall was about to give and then rebuild it while the messenger rode to the emperor and back. When the Sui Empire finally pushed for the capital with 100 days of food on every man’s back, the Koreans emptied the countryside ahead of them, lost 7 small fights in one day on purpose to pull them in deeper, and waited for hunger to turn them around before hitting them halfway across a river.
7. The Winter War (1939-40, Finland vs. the USSR): 3.7 million Finnish people were invaded by a Russian nation of 170 million, with 32 tanks against roughly 2,500 and 114 aircraft against 3,880. But, their advantage was terrain. Finnish ski troops in white camouflage cut the road-bound Soviet columns into isolated pockets and finished them one at a time, and 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. Finland still lost the war. It signed away 9% of the country and watched 422,000 people pack what they could carry and leave, but it was still a country, which had been the entire objective.
8. Afghan resistance vs. Britain and the USSR (1839-42 and 1979-89): 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 exactly one man rode into the garrison at Jalalabad, an army surgeon named William Brydon. The Soviets pushed 620,000 personnel through over 9 years and withdrew in 1989 having changed nothing. Afghanistan gives an invader nothing worth capturing, because power lives in the valleys and not the capital, so no one’s surrender binds anybody else.
9. The American Revolution (1775-83): Never more than 48,000 men under arms at once and a navy that peaked at 31 vessels against a Royal Navy of 478, and they won by keeping an army alive for 8 years until an empire 3,000 miles away ran out of reasons to keep paying for it.
10. The Haitian Revolution (1791-1804, Toussaint Louverture): 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).
11. Swiss pikemen vs. Habsburg and Burgundian knights (1476): Europe’s poorest mountain farmers made themselves into its most expensive soldiers. In 1476 the richest army on the continent lost between 6,000 and 10,000 men to a Swiss force that buried 410 of its own, because a block of 18-foot pikes moving at a jog cannot be charged by cavalry, and kings eventually found it cheaper to just hire them.

Every advantage has an expiration date

The Swiss are the right place to end, because their story has the lesson I keep coming back to. 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.

The same thing is true of everything on this list. The environment gets scouted and the tools get copied, and sooner or later the stronger side takes you seriously. The one choice that does not expire is the 4th, 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, and I think realized that sometimes the thing you give up is being in the fight at all.

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