There's a very interesting article in the New Yorker magazine with this title, studying how the underdog can turn the tables on the 'top dog' in a fight or competition, and come out victorious. The author, Malcolm Gladwell, draws examples from business, sports and war to make his point.
Here are a few brief excerpts to whet your appetite.
The political scientist Ivan Arreguín-Toft recently looked at every war fought in the past two hundred years between strong and weak combatants. The Goliaths, he found, won in 71.5 per cent of the cases. That is a remarkable fact. Arreguín-Toft was analyzing conflicts in which one side was at least ten times as powerful — in terms of armed might and population — as its opponent, and even in those lopsided contests the underdog won almost a third of the time.
In the Biblical story of David and Goliath, David initially put on a coat of mail and a brass helmet and girded himself with a sword: he prepared to wage a conventional battle of swords against Goliath. But then he stopped. “I cannot walk in these, for I am unused to it,” he said (in Robert Alter’s translation), and picked up those five smooth stones. What happened, Arreguín-Toft wondered, when the underdogs likewise acknowledged their weakness and chose an unconventional strategy? He went back and re-analyzed his data. In those cases, David’s winning percentage went from 28.5 to 63.6. When underdogs choose not to play by Goliath’s rules, they win, Arreguín-Toft concluded, “even when everything we think we know about power says they shouldn’t.”
. . .
It is easier to dress soldiers in bright uniforms and have them march to the sound of a fife-and-drum corps than it is to have them ride six hundred miles through the desert on the back of a camel. It is easier to retreat and compose yourself after every score than swarm about, arms flailing. We tell ourselves that skill is the precious resource and effort is the commodity. It’s the other way around. Effort can trump ability — legs, in Saxe’s formulation, can overpower arms — because relentless effort is in fact something rarer than the ability to engage in some finely tuned act of motor coördination.
. . .
In 1981, a computer scientist from Stanford University named Doug Lenat entered the Traveller Trillion Credit Squadron tournament, in San Mateo, California. It was a war game. The contestants had been given several volumes of rules, well beforehand, and had been asked to design their own fleet of warships with a mythical budget of a trillion dollars. The fleets then squared off against one another in the course of a weekend. “Imagine this enormous auditorium area with tables, and at each table people are paired off,” Lenat said. “The winners go on and advance. The losers get eliminated, and the field gets smaller and smaller, and the audience gets larger and larger.”
Lenat had developed an artificial-intelligence program that he called Eurisko, and he decided to feed his program the rules of the tournament. Lenat did not give Eurisko any advice or steer the program in any particular strategic direction. He was not a war-gamer. He simply let Eurisko figure things out for itself. For about a month, for ten hours every night on a hundred computers at Xerox PARC, in Palo Alto, Eurisko ground away at the problem, until it came out with an answer. Most teams fielded some version of a traditional naval fleet—an array of ships of various sizes, each well defended against enemy attack. Eurisko thought differently. “The program came up with a strategy of spending the trillion on an astronomical number of small ships like P.T. boats, with powerful weapons but absolutely no defense and no mobility,” Lenat said. “They just sat there. Basically, if they were hit once they would sink. And what happened is that the enemy would take its shots, and every one of those shots would sink our ships. But it didn’t matter, because we had so many.” Lenat won the tournament in a runaway.
There's much more at the link. Very interesting, and recommended reading.