The Millennium Challenge, as became evident a few months later, when the United States invaded Saddam Hussein-led Iraq, was a full dress rehearsal for war. In the wake of the Persian Gulf War in 1991, the Pentagon became convinced that conventional warfare, where two armies fought head on, would no longer be an effective method of warfare: war would take place in cities as well as battlefields, and involve economies and cultures as much it involved weapons.

There were two teams: Blue Team, which had greater intellectual resources than perhaps any army in history and essentially had every resource of the Pentagon available at their disposal. The Blue Team looked at the full array of what it could do to its opponent’s environment – political, military, economic, social, cultural, and institutional. This was all intended to make crystal clear the resources, attitudes, and intended moves of the enemy – and Van Riper was selected because he truly believed that you could not know everything about the enemy. Van Riper was not against the type of extensive analysis that the Blue Team was performing but thought that it was inappropriate in the midst of battle, where the uncertainties of war and the pressures of time made it impossible to compare options carefully and calmly. The Millennium Challenge was thus not only a battle between two armies, but also between diametrically opposed military philosophies.

On the opening day of the simulation, the Blue Team sent 10,000 troops into the Persian Gulf, parked an aircraft carrier battle group offshore the Red Team’s home country, and demanded surrender from the Blue Team – acting with utter confidence and ostensibly knowing where all of the Red Team’s vulnerabilities were and what possible moves it would make. However Van Riper did not act as the computers predicted. The Blue Team had destroyed all lines of electronic/fiber-optic communication, assuming that the Red Team would be forced to rely on easily intercepted satellite communication. Van Riper instead used messages hidden inside prayers and motorcycles to communicate. Schooled in military history, he used WWII-era methodology to circumvent the modern technology that would give away his moves.

On the second day of the game, Van Riper put a fleet of small boats in the Gulf to track the ships of the invading Blue Team navy. Then without warning, he bombarded the navy in an hour-long assault with cruise missiles. In the end, 16 American ships were at the bottom of the Gulf; had this been a real war, 20,000 American servicemen and women would have dead, without the Americans having fired a single shot. Analysts attempted to give different explanations, but none could fathom the fact that the Blue Team suffered a huge loss.
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Gladwell returns to the war game. The Pentagon is silent at first, but then reverses time: they refloat the boats at the bottom of the Gulf, telling Van Riper that the ballistic missiles he used at first were all shot down with a new kind of missile defense, and the assassinations Van Riper carried out of pro-American leaders in the region had negligible effects. In the second round of the Millennium Challenge, the Blue Team wins – there were no surprises, no insights, and no opportunities for the confusion and complications of the real world. At the end of the second experiment, the Pentagon was satisfied, as the military was transformed and the Pentagon confidently turned its attention to the real Persian Gulf a few months later.