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What did the war game umpires do? They instantly refloated the Blue fleet and forced the Red Team to relocate its anti-aircraft assets out of range for taking out the attacking Blue aircraft. This time Team Blue prevailed. What had begun as an unscripted exercise became heavily scripted after the bad guys declined to play by the rules anticipated by the good guys.

In war games as well as in the real world, creative enemies can identify and exploit defensive weakness to launch a successful surprise attack.[36] Let us return to the case of Pearl Harbor, an attack brilliantly analyzed by Roberta Wohlstetter in her Bancroft Prize–winning study, Pearl Harbor: Warning and Decision (1962). The catastrophic intelligence failure leading to what FDR called “a date that will live in infamy,” she writes, was the result of failings deeply rooted in human nature and organizational structure. First, intelligence officers were unable to separate the wheat from the chaff—in communications parlance, signals from background noise. Second, given ambiguous information susceptible of multiple good faith interpretations, the natural human impulse is to choose an interpretation consonant with one’s own instinctive preferences and values.

Further compounding such failures was the inability of recipients of strategically decisive information to place that information in the hands of President Roosevelt and senior military leaders due to “stovepiping”—failing to share critical data among disparate agencies. Collectively the problem of extracting and then acting on the correct signals from the flood of intelligence data has been nicknamed by intelligence officials the “Roberta problem.”

The Roberta problem was operative in the days before December 7, 1941: U.S. decision makers who made the fatal strategic call placed higher value on the fact that Japan’s diplomats were still talking in Washington than on the interception of the message “east wind rain” extracted from Japan’s top-secret diplomatic code, a signal that a possible attack operation was underway. A Japanese attack on American bases in the Philippines was thought a real prospect (and in fact happened on December 8), but the U.S. commanders did not seriously consider the far more daring strike at Pearl Harbor a possibility. Weren’t its waters too shallow to allow torpedo planes to attack? The only alert that military officials ordered for the Pearl Harbor area was to watch out for local saboteurs.

Even when troops are massed at a border it is possible to be caught flat-footed. For months in the summer of 2008, Russian troops and equipment were building up along Russia’s border with U.S. ally Georgia. Despite this ominous sign, as noted in chapter 3, the administration did not expect a Russian invasion while President Bush—and Russian president Vladimir Putin—were attending the Beijing Olympic Games.

Roberta problems can exist even after the fact, when analysts persist in blindness to salient features of an event. In November 2009, an American Muslim—whose private business card described him as a “soldier of Allah”—shouted “Allahu Akbar!” as he gunned down his fellow soldiers at Fort Hood in Texas. President Obama accepted a Pentagon report on the incident that contained nary a reference to militant Islam nor to the shooter’s Islamist beliefs. The Defense Department treated the shooter as if he were simply a lone, mentally disturbed gunman.

Iraq I, Iraq II

THE YEAR 1932 was a fateful augury for America not only because of the Pearl Harbor war game and the U.S. military’s failure to learn the right lessons. It was coincidentally the year that a new nation was born in the Mideast: Iraq under British sponsorship. America’s history with Iraq and intelligence was an embarrassment long before facts disproved CIA director George Tenet’s “slam dunk” conclusion regarding Iraq’s weapons of mass destruction. The roots of Tenet’s mistake were partly generic—the difficulty of amassing and analyzing intelligence information on a closed society run by a mercurial tyrant—but also deeply set in the prior intelligence failure in the run-up to the Gulf War.

In their 1995 book The Generals’ War, Michael Gordon and retired general Bernard Trainor detail the intelligence debacle of 1990 that led to the 1991 conflict. In March 1990 American intelligence verified that Iraq had deployed short-range Scud missiles inside western Iraq and in Syria; soon after came Iraqi threats to “burn half of Israel.” American and British agents intercepted components for Saddam’s “supergun” project—a monster artillery piece that was to hurl projectiles several hundred miles. (The project was ultimately stopped by—who else?—Israel, whose agents killed the designer in a Paris hotel.) In May 1990, the Bush administration suspended $500 million in commodity credits (to ratchet up pressure on Saddam for his aggressive posture). But neither defense nor intelligence officials discussed the Iraqi threat. A Pentagon study from Saddam’s first year as president of Iraq (1979) counseled moving forces into the Mideast early to head off Saddam’s possible aggression.

As Iraq escalated its intimidation of Kuwait—complaining that Kuwait’s oil-pricing policy hurt Iraq’s economy—members of the Bush administration began to pay closer attention. On July 25 Charles Allen, the national intelligence officer for warning, placed a 60 percent warning-of-war probability on Saddam invading Kuwait. The Pentagon’s top Iraq analyst also stepped up warnings, but his calls did not resonate with his Pentagon superiors. Diplomatic signals went the other way—Egypt, Saudi Arabia, and other Arab states assured Washington that Arab diplomacy would resolve the crisis. The U.S. dispatched two tankers and a transport plane to the United Arab Emirates, just in case.

With his troops massed and ready on the Iraqi-Kuwait border, Saddam summoned America’s ambassador to Iraq, April Glaspie, to a midnight meeting late that July. She assured Saddam Hussein that our military deployment to the United Arab Emirates was not intended as a threat to Iraq, and that the U.S. had peaceful intentions. Saddam disclaimed any intent to invade but warned Glaspie: “Do not push us to it; do not make it the only option left with which we can protect our dignity.” Her secret diplomatic post-meeting cable to senior U.S. officials concluded that Saddam, “is worried…. He does not want to further antagonize us. With the UAE maneuvers we have finally caught his attention…. I believe we would now be well-advised to ease off on public criticism of Iraq until we see how the negotiations develop.”

Senior Bush officials were split as to Saddam’s likely next moves. President Bush sent a message to Saddam asserting that everyone had “a strong interest in preserving the peace and stability of the Middle East,” while expressing “fundamental concerns about certain Iraqi policies and activities.” He called for both countries to “maintain open channels of communication to avoid misunderstanding and in order to build a more durable foundation for improving our relations.” Bush sent the message on July 28 for Glaspie to deliver to Saddam before she departed Baghdad on July 30 for vacation.

By August 1 intel warning chief Allen raised his war probability to 70 percent. But military analysts and commanders thought that even if Saddam moved he would only perhaps seize the northern Kuwaiti oil fields and occupy Kuwait’s offshore islands. Even while realizing that Iraq’s land force was large enough not only to overrun Kuwait but also to seize Saudi Arabia’s Eastern Province, the Bush administration did not make a single consequential military move prior to Saddam’s August 2 invasion.

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History is full of examples of strategic surprises, in which enemies launch successful attacks by acting contrary to expectation: noteworthy instances in the twentieth century, besides Pearl Harbor, include Japan’s destruction of Russia’s fleet in the 1904 Russo-Japanese War, Israel’s preemptive strike on Egyptian airfields at the start of the 1967 Six-Day War, and Egypt’s attack to start the 1973 Yom Kippur War. In the run-up to the June 22, 1941, massive Nazi invasion of Russia, Stalin ignored warnings from Winston Churchill, choosing instead to trust Hitler, with whom he had made a nonaggression pact one week before Hitler started World War II. Hitler’s pivot to the Eastern Front caught Russia completely by surprise.