The subject of strategic surprise is a large one, and it has inspired a fair amount of theoretical literature. The following catalogue isn’t intended as a contribution to theory. It is the evidence behind my personal observation that, for as long as I have studied the Middle East, all of the profoundly formative events have been “black swans,” imagined or predicted by almost no one. For an expert, that’s humbling (or should be).

But, first, what is a black swan? For centuries, it was assumed in Europe that all swans were white. The phrase “black swan” was used as we would use “flying pig”: a metaphor for something that couldn’t exist. But then a 17th-century Dutch explorer observed a black swan in Australia. That single sighting demolished an assumption that had stood since time immemorial.

The concept of a black-swan event was popularized a few years ago in a bestselling book with that title. Its flamboyant author, Nassim Nicholas Taleb, argued that the most dramatic changes in politics, economics, and technology come out of the blue. A black-swan event, ran his definition, “lies outside the realm of regular expectations, because nothing in the past can convincingly point to its possibility” (my emphases).

So a black-swan event is more extreme than a low-probability event. A black-swan event has no prior indication that it’s even possible. It’s unthinkable. And yet, Taleb concluded, while black swans themselves are rare, we live in a world largely fashioned by such once-unthinkable events. This wasn’t an entirely original argument, but his showmanship turned “black swan” into a common figure of speech.

Of course, what constitutes a black-swan event is a matter of perspective. Your assumptions may be upended by a surprise attack, but it’s no surprise to the attacker. For example, the June 1967 Six-Day War, preemptively initiated by Israel, was a black-swan event for Egypt, but obviously not for Israel.

In what follows, the perspective I assume is American. My seven black-swan events not only took Washington by surprise, but had far-reaching impacts on U.S. interests and policies. Also, while it’s tempting to go way back in time for more examples, I’ll limit myself to events within living memory, which (depending on your age) you probably remember, too.

Before we plunge in, it’s also important to remember this: inevitably, many a black-swan event has been preceded by evidence suggesting the possibility of a black-swan event. In fact, some observers, seeing the evidence, may even have a premonition of the event itself. Such “[p]rescient memos are a dime a dozen in Washington after a crisis,” wrote the late Christopher Hitchens. “They are often then read for the first time, or leaked to the press or Congress.”

But the evidence and the memos aren’t sufficiently convincing, because they don’t come together in a story that’s more persuasive than the prevalent one. Here, too, it’s a matter of perspective. A black-swan event is a black-swan event not because no one has imagined it, but because it was unimaginable to the people who mattered.

Who mattered? The ones who could have prevented it in the first place.

1. 1973: “Simply, obviously, and starkly wrong”

ARABS AND ISRAELIS BATTLE ON TWO FRONTS;
EGYPTIANS BRIDGE SUEZ; AIR DUELS INTENSIFY
—New York Times, front-page headline, October 7, 1973

It wasn’t only Israel that was taken by surprise in 1973 when Egypt and Syria attacked Israel across the Suez Canal and the Golan Heights. So were U.S. intelligence agencies.

On October 6, the very day of the surprise attack, the CIA estimated that “for Egypt, a military initiative makes little sense at this critical juncture,” while “for the Syrian president [Hafez al-Assad], a military adventure now would be suicidal.” An internal memo from the National Security Council noted that while the Israelis had become persuaded that an attack might be in the works, “our intelligence services have continued to downplay the likelihood of an Arab attack on Israel and still have no signs that such action is imminent.”

A CIA post-mortem from December 1973 admitted that the agency’s estimates “were—quite simply, obviously, and starkly—wrong.” It wasn’t for a lack of information. “Such information (derived from both human and technical sources) was not conclusive but was plentiful, ominous, and often accurate.” But all of these raw data were filtered through preconceptions about Arab intentions and capabilities.

As with every black-swan event, it all seemed so obvious afterward. But as the post-mortem notes, “what may seem so clear now did not, could not, seem so clear then.”

This wasn’t just Israel’s problem: by 1973, the Israeli-Arab conflict had become embedded in the cold war, and when Israel finally did gain the upper hand on the battlefield, the Soviets threatened direct intervention. U.S. nuclear forces went to Defcon 3. The Soviets backed down: as Soviet premier Alexei Kosygin put it, “it is not reasonable to become engaged in a war with the U.S. because of Egypt and Syria.”

But the other effects of the war remade the Middle East.

2. “Iran is not in a revolutionary situation”

SHAH LEAVES IRAN FOR INDEFINITE STAY;
CROWDS EXULT, MANY EXPECT LONG EXILE
—New York Times, front-page headline, January 17, 1979

In his recent memoir of the Carter years, Stuart Eizenstat writes: “One could fill an ocean with what the United States did not know about developments in Iran.”

When President Jimmy Carter came into office in 1977, the State Department reassured him that the shah of Iran, “in fine health, and protected by an elaborate security apparatus, has an excellent chance to rule for a dozen or more years.” In August 1978, as popular discontent built, the CIA still concluded that “Iran is not in a revolutionary or even a pre-revolutionary situation. There is dissatisfaction with the shah, but this does not at present threaten the government.” Even when, three months later, the U.S. ambassador in Tehran finally wrote a memo entitled “Thinking the Unthinkable,” few were willing to think it.

In hindsight, all the evidence was there. (It always is.) Israel’s ambassador to Iran, Uri Lubrani, as early as June 1978, had reported that the erosion in the shah’s position was “accelerated and irreversible,” and that it would

culminate in his fall and a drastic change in Iran’s form of government. It’s very hard to estimate the time frame. My very personal estimate, which isn’t based on any objective data, it that the range is more or less five years.

Even this perceptive take overestimated the shah’s shelf life. He fled the country only eight months later.

Because Washington assumed the shah’s omniscience and omnipotence, it misread all of the signs. Ayatollah Khomeini gave birth to the Islamic Republic, the American embassy was taken hostage for over a year, and today, 40 years later, the United States is still locked in struggle with Iran.

And the Middle East? Nothing has done more than Iran’s revolution to transform it.

3. Soviet invasion: “Considered highly unlikely”

AFGHAN PRESIDENT IS OUSTED
AND EXECUTED IN KABUL COUP,
REPORTEDLY WITH SOVIET HELP
—New York Times, front-page headline, December 28, 1979

When Soviet troops poured into Afghanistan in December 1979, Washington was dazed. The Soviet Union was the number-one target of U.S. intelligence collection and analysis. Intelligence might be off on Egypt or Syria, but the United States spared no means to surveil the USSR, with its vast nuclear arsenal and its huge military divisions in Europe.

In fact, there was plenty of raw intelligence—how could there not be? But no one thought the Soviets would be so stupid as to invade. The CIA’s post-mortem admitted that a Soviet invasion “was considered highly unlikely” because the political and military costs would be “too high.” Even when evidence accumulated of an impending move, “the idea that the Soviets would actually pay the price of invading seemed so outrageous that it was estimated that only a small force would be committed.” The warning signs never coalesced into a clear warning—hence the shock in Washington when the Soviets sent in three full divisions, upward of 30,000 troops.

An after-the-fact internal investigation rushed to reassure policymakers that if the Russians tried to pull the same fast one in Europe, U.S. intelligence authorities would know it well in advance. It’s just that Afghanistan was . . . well, a bit off the U.S. radar. The invasion led swiftly to the so-called “Carter Doctrine,” declaring the Persian Gulf an American lake. It was followed by a ten-year proxy war waged by the CIA against the Soviets in Afghanistan, with consequences that last until today.

4. Kuwait: “Saddam would not be so foolish”

INVADING IRAQIS SEIZE KUWAIT AND ITS OIL;
U.S. CONDEMNS ATTACK, URGES UNITED ACTION
—New York Times, front-page headline, August 3, 1990

Was the Iraqi invasion of Kuwait in the summer of 1990 a total surprise? Through the first half of 1990, an office in the CIA did issue warnings, especially as the United States detected the movement of Iraqi forces. The CIA officer who issued the warnings would later write:

Indicators were assessed early and accurately. Our prior assessment of timelines for war preparations proved correct. Policy officials were informed of our conclusions at each major stage in the development of the threat, personally as well as in writing. Nevertheless, the warning messages—both warning of war and warning of attack—were not heeded, either by senior intelligence officials or by policymakers.

 Why not? To them, it was unthinkable. Iraq’s dictator, Saddam Hussein, would never dare. He might do a limited grab of Kuwaiti territory, some surmised. But as April Glaspie, the U.S. ambassador to Iraq, later admitted, “I didn’t think, and nobody else did, that the Iraqis were going to take all of Kuwait.” Edward Gnehm, the prospective U.S. ambassador to Kuwait at the time, would recall that

no one in a position of responsibility to my knowledge seems to have considered the possibility that Saddam was going to overrun all of Kuwait. There wasn’t even a consensus that Saddam intended to invade at all. Even though the CIA had changed their assessment, there were others who still said an invasion was ridiculous.

Much fog was spread by friendly Arab leaders, foremost among them Egypt’s President Hosni Mubarak. According to Defense Secretary Dick Cheney, these leaders claimed that “Saddam was bluffing” and “urged us not to take any steps that would provoke” him. The Soviets also issued reassurances. “Don’t worry, nothing is going to happen,” Eduard Shevardnadze, the Soviet foreign minister, assured his American opposite, James Baker. “Saddam would not be so foolish.” And since, Baker recalled, Iraq was a client state of the Soviets, “surely the Arabists back in Moscow would know what was going on.”

Since the CIA warnings were already ambiguous, the views of Arabs and Russians tilted the assessment made by U.S. leaders. Iraq then invaded Kuwait, ushering in the era of American boots on the ground in the Middle East.

5. 9/11: “Failure of imagination”

U.S. ATTACKED
HIJACKED JETS DESTROY TWIN TOWERS
AND HIT PENTAGON IN DAY OF TERROR
—New York Times, front-page headline, September 12, 2001

“The 9/11 attacks were a shock,” the 9/11 Commission later found, “but they should not have come as a surprise. Islamist extremists had given plenty of warning that they meant to kill Americans indiscriminately and in large numbers.” Four months before the attacks, for instance, Louis Freeh, the FBI director, said that al-Qaeda was bent on “the planning and carrying out of large-scale, high-profile, high-casualty terrorist attacks against U.S. interests and citizens and those of our allies, worldwide.”

But the world is a wide place, and conventional wisdom held that al-Qaeda would most likely strike in the Middle East or Africa. Even a dozen intelligence reports on al-Qaeda’s possible use of hijacked planes as weapons didn’t dent that assumption. Neither did a daily intelligence brief given to President George W. Bush a month before the attacks, headlined: “Bin-Ladin Determined to Strike in U.S.’’

The 9/11 Commission found multiple sources of dysfunction in the way the bureaucracy handled intelligence, but the greatest weakness was what it called a “failure of imagination.” As a result, the commission concluded,

the domestic agencies never mobilized in response to the threat. They did not have direction, and they did not have a plan to institute. The borders were not hardened. Transportation systems were not fortified. Electronic surveillance was not targeted against a domestic threat. State and local law enforcement were not marshaled to augment the FBI’s efforts. The public was not warned.

All this has changed since 9/11, but not before the attacks utterly transfigured America’s role in the Middle East.

6. “Oh, my goodness, Hamas won?”

HAMAS ROUTS RULING FACTION,
CASTING PALL ON PEACE PROCESS
—New York Times, front-page headline, January 27, 2006

It was President George W. Bush, convinced of America’s democratizing mission, who pushed for elections in the West Bank and Gaza in January 2006. And it seemed to make good sense. Palestinian polls showed that the faction led by Mahmoud Abbas would defeat Hamas handily. An electoral victory, it was thought, would solidify his rule, enabling him to strike a peace deal with Israel.

As the votes were counted, Secretary of State Condoleezza Rice was doing her early-morning workout in the fitness center of her apartment complex. Looking up, she saw these words crawl across the television screen: “In wake of Hamas victory, Palestinian cabinet resigns.” Astonished, she called her office.

I said, “What happened in the Palestinian elections?” And they said, “Oh, Hamas won.” And I thought, “Oh, my goodness, Hamas won?” I thought, might as well finish exercising. It’s going to be a really long day.

Hamas didn’t just win; it won in a landslide. “Nobody saw it coming,” Rice told reporters. “I don’t know anyone who wasn’t caught off-guard by Hamas’s strong showing.”

As I demonstrated at the time, misleading polls played a major role. But even these were filtered through the template of democracy-promotion, with its settled tendency to believe that moderation must triumph.

In relaying the bad news, the New York Times reported these words by Ephraim Halevy, a former head of Mossad: “The era of the pretend peace process is over.” The splitting of Palestinian legitimacy, soon to be made tangible by Hamas’s physical seizure of Gaza, destroyed not only the meager prospects for an agreement but the very process itself.

7. Arab Spring: “We were lax”

MUBARAK OUT
EGYPT EXULTS AS YOUTH REVOLT ENDS 3 DECADES OF IRON GRIP
—New York Times, front-page headline, February 12, 2011

Right up until the “Arab Spring” of 2011, Arab regimes seemed immovable. Then, all of a sudden, mass protests toppled dictators in Tunisia, Egypt, Libya, and Yemen. In the last two, and in Syria, instability would deteriorate into civil war.

Michael Morell, the then-deputy director of the CIA, admitted the agency’s failure:

We failed because to a large extent we were relying on a handful of strong leaders to help us understand what was going on in the Arab street. We were lax in creating our own windows into what was happening, and the leadership we were relying on was unaware of the tidal wave that was about to hit them.

This “outsourcing” of assessments to allies and friends is the origin of many a surprise. Surely, the reasoning goes, the Israelis will know before we do whether they face an attack? Surely the shah will know before we do whether he’s in danger? Surely our Arab friends will know before we do whether Saddam is going off the rails? If our friends are complacent, why should we be alarmed?

America’s allies in the Middle East do provide the U.S. with vital intelligence and insights. But their blind spots also become Washington’s.

Today there is a whole industry trying to explain the Arab Spring—in hindsight. This is supposed to establish a set of warning signs for when it might happen next. Nassim Nicholas Taleb, the man who popularized the “black swan” concept, dismisses such efforts:

The final episode of the upheaval in Egypt was unpredictable for all observers, especially those involved. As such, blaming the CIA is as foolish as funding it to forecast such events. Governments are wasting billions of dollars on attempting to predict events that are produced by complex systems and are therefore not statistically understandable at the individual level.

The catalogue I’ve just provided could have been expanded, but these seven instances make the point: the most far-reaching changes in the Middle East caught American experts by surprise.

It’s customary to describe these instances as “intelligence failures.” The information was there; lacking was the imagination. But it is naive to think that such events can be predicted at all. There are always warning signs, of course, but they won’t be sufficiently convincing to overturn long-held assumptions grounded in past experience. If that is the case, then no matter how much intelligence is collected, surprise will follow surprise.

You might think that the best experts, at least, would have an advantage when it comes to predicting outlier events. But looking back, I can’t think of anyone who’s actually done it. Some, however, have detected trends. One who did so was the late Bernard Lewis, who in 1976 published a maverick essay in Commentary entitled “The Return of Islam.” It was brilliant, and Lewis wrote it two years before the Iranian revolution. But he didn’t mention Iran, instead focusing on the Arabs.

About the Iranian revolution, Lewis would later say: “I must confess I’d never heard of Khomeini. Who had?” Even if you had been persuaded by his 1976 article, you would still have been surprised by the revolution in Iran.

So detecting trends isn’t the same as predicting events, especially black-swan events. And even if you could, who would believe you? You’d be labeled a fantasist. And if you turned out to be wrong, you’d be ridiculed; Washington is no more forgiving than Wall Street. There is much to be said for the maxim widely misattributed to John Maynard Keynes: “It’s better to be roughly right than precisely wrong.” That’s why the wisest Washington oracles keep their forecasts vague.

If predicting the unpredictable is mission impossible, what should experts do? The answer: plenty. When black-swan events do occur, as they must, policy is thrown into disarray, the reputations of rash forecasters crumble, and a scramble ensues. This is precisely when a well-timed intervention can make a difference. Expertise and imagination are an advantage, not in predicting black swans but in responding to them. Each black swan is an opportunity, to be either seized or wasted.

Henry Kissinger was the master here. Although totally surprised by the outbreak of war on Yom Kippur in 1973, he understood that it created an opening for the United States. His wartime maneuvers and his subsequent “shuttle diplomacy” put Egypt in America’s camp and laid the cornerstone of its peace with Israel.

Ronald Reagan was also adept at seizing the opportunity. After his election, he turned the surprise Soviet move into Afghanistan into a covert CIA war that bled the Soviets dry, and ten years later helped to bring down the Soviet Union.

By contrast, the Bush II team wasted their black swan by leveraging the disarray that followed 9/11 in an effort to spread democracy, beginning in Iraq. That ended up weakening the pax Americana.

The mission, then, is clear. Since surprises will happen, it is crucial to be the first to forge a new paradigm out of the wreckage while Washington is grasping for ideas. In that sense, most of what experts do is in patient preparation for the day when assumptions come tumbling down.

And when will the next opportunity arise? I wish I knew, but if I told you, you wouldn’t believe me anyway. Yet of one thing I’m certain. The next black swan is quietly and directly gliding our way.