From October 7 to Killing Khamenei

How a single attack launched across Gaza’s border mushroomed into a 28-month-long conflict entangling at least 18 countries while claiming tens of thousands of lives.

By Michael Oren

Officially, at least, the war against Iran began on Saturday, February 28, at 1:15 a.m., Eastern Standard Time. In reality, though, Operation Epic Fury of the United States and Israel’s Roaring Lion began at 6:29 in the morning, Middle East Time, on October 7, 2023.

In launching the Al-Aqsa Flood onslaught, Hamas leader Yahya Sinwar believed he was initiating the long-desired destruction of the Jewish State and the final triumph of radical Islam. Little could he have conceived that, 875 days later, Israel would not only have survived but emerged as the region’s preeminent military power while Iran, the former jihadist hegemon, was reduced to an embattled remnant. Sinwar, along with a broad list of the Palestinian, Iranian, and Lebanese leaders who started and supported this war, would be dead.

How did that happen? How did a single attack launched across Gaza’s border, that lasted a little over a day and killed 1,200 Israelis, mushroom into a 28-month-long conflict entangling the United States and at least 17 other countries and claiming tens of thousands of lives? What concatenation of events transformed that brutal but localized battle into the full-blown war whose conclusion, as of this writing, remains totally unpredictable? The answer to such questions can be summarized in a single word: miscalculation.

Just about every war begins with one. There was the Austro-German belief that the suppression of a Serbian revolt in the summer of 1914 would not trigger a counterattack by France and Russia or Japan’s 1941 attack on Pearl Harbor, designed to keep America out of World War II. Throughout history, the misreading of an adversary’s intent, the over or underestimation of its resolve, has led to countless clashes, localized and global. Yet few wars of the past can compete with the current Middle East conflict in terms of the sheer number of miscalculations that precipitated it.

The original misjudgments were Israel’s. Following its 2014 clash with Hamas—Operation Protective Edge—the Israeli government concluded that Sinwar was ready to hang up his jihadist hat and don a sovereign one, focusing on Gaza’s development. Deterred and contained by the Israel Defense Forces (IDF), Hamas could be further incentivized to keep the peace through generous installments of Qatari cash. Thus was born the conceptzia, the assumption that Israel had nothing more to fear from Hamas and could concentrate its intelligence and defense assets on the far more ominous threats to the north.

I was a deputy minister in the Israeli government from 2016 to 2019, dealing extensively with Gaza, and can attest to the fact that the conceptzia was almost universally embraced. Not only Prime Minister Benjamin Netanyahu and other Israeli leaders subscribed to it, but also the heads of the security services—the army, Mossad, and Shin Bet—and every U.S. president from Barack Obama to Donald Trump.

Along with the delusion of Hamas’s pacification, Israelis presumed that we could tear our society apart over the government’s proposed judicial reforms and not signal vulnerability to our foes. While Netanyahu and his ministers ignored repeated intelligence warnings that the deep social schisms wrought by its attempt to neuter the Supreme Court could entice Iran and Hezbollah to attack, the myriad Israelis who, in protest, refused to report for reserve duty further allured them. “[The] protests indicate that the internal state of the [Zionist] entity is unprecedented,” said Hamas political chief Ismail Haniyeh in September 2023. “We are advancing toward a widespread explosion point.”

Haniyeh was not alone in foreseeing a major clash. “I don’t want to shock you,” I told an Old Parkland campus audience in Dallas on October 5. “But Israel will soon be at war.” As evidence, I adduced not only the country’s civil strife but, more determinatively, the reports of an impending Saudi-Israeli treaty. “If anybody thinks Iran will sit quietly while its two worst enemies make peace, they’re kidding themselves.”

The conceptzia nevertheless reigned supreme, assuring that Hamas would catch Israel entirely off guard. On the morning of October 7, a mere 1,500 soldiers were posted along the 37-mile-long Gaza border, and half of them were on leave for the Simchat Torah holiday. Of Israel’s formidable fleet of 48 Apache attack helicopters, only two were on alert, both in the north, along with a single Zik attack drone. Yet, ultimately, Israel’s miscalculations paled beside Sinwar’s.

In addition to dividing Israelis even deeper, Sinwar assumed that Operation Al-Aqsa Flood would trigger a multifront assault. Hezbollah, the Houthis, and other Iranian proxies throughout the region would also join in the attack, as would Iran itself. The Palestinians in the West Bank and throughout Israel would rise in revolt, crumbling the Jewish state from within. “We will come to you with endless rockets. . .a limitless flood of soldiers [and]. . .millions of our people, like the repeating tide,” Sinwar predicted. “A nuclear explosion from across the region” would obliterate Israel.

Rather than sowing division, the massacre of their citizens in the south instantly united Israelis and spurred them to counterattack. Meanwhile, the pan-Islamic pile on Sinwar anticipated never materialized. Although Hezbollah launched drone and rocket strikes against Israel, its elite Radwan forces refrained from invading Northern Galilee. The Houthis, together with the Iranian-backed militias in Syria and Iraq, also shelled Israel intermittently, but their contributions to Hamas’s war efforts remained minimal. And apart from issuing bellicose statements, Tehran’s ayatollahs remained passive.

But the miscalculations had scarcely begun. By the spring of 2024, with the fighting concentrated in Gaza and, in Southern Lebanon, confined to artillery duels, the United States and Israel concluded that Iran would not take an active part in the war. They were wrong. On April 13, in response to an Israeli missile strike on a military annex of its embassy in Damascus, Iran fired 320 projectiles—ballistic missiles, cruise missiles, and drones bearing more than 60 tons of high explosives—at Israel. Though the vast bulk of these were intercepted, Iran had demonstrated its willingness and ability to engage in the conflict directly and not solely through proxies. Still, when Iran launched another 200 missiles at Israel in October, Washington and Jerusalem again seemed surprised.

By that time, the transformative effects of the next miscalculation were already being felt. This error was Hassan Nasrallah’s in assuming that Israel remained, as he disparaged it, “weaker than a spider web,” and would not retaliate robustly against Hezbollah’s daily shelling of the country’s north. That hypothesis was exploded—literally—by the Mossad on September 7 with the thousands of booby-trapped pagers it had supplied to Hezbollah terrorists and, the following day, by hundreds of similarly primed walkie-talkies. Nasrallah also thought he could hide from Israeli retribution, only to be killed in his bunker, 60 feet under Beirut, by IDF jets.

After steamrolling Hezbollah, the miscalculation ball reverted to the American-Israeli court. Successfully executing last June’s Rising Lion/Midnight Hammer campaign against Iran, Trump and Netanyahu appeared to conclude that the ayatollahs were chastised and would not mount another military challenge. Neither considered the possibility that the Iranians, having withstood the wrath of the world’s greatest superpower and its most lavishly armed ally for a full 12 days, might have considered themselves the victors. Witnessing how, after performatively firing several barrages at Qatar, Trump immediately agreed to a ceasefire, might also have misled the Iranians into thinking that the president was more bluff than bite. So, too, was Trump’s failure, to date, to fulfill his pledge to disarm Hamas. Brazenly, the regime rebuilt and expanded its ballistic-missile stockpiles and showed no intention of abandoning its nuclear dreams, confident that its enemies would not again intercede. This was also a mistake.

The march of miscalculations, meanwhile, continues. By firing rockets and drones at Arab countries—even presumptive allies such as Oman—and the British base in Cyprus, Iran thought it could generate international pressure on Trump to agree to a ceasefire. Instead, Iran looks like it has expanded the number and nationalities of the warplanes attacking it—Saudi Arabia and the United Arab Emirates, alone, have 500—and risked eliciting an armed response from the North Atlantic Treaty Organization (NATO). But as the war rages on, the paramount question will remain whether it, too, was ill-conceived.

To be sure, not all wars that begin with blunders end with one. The Second World War is a case in point, as is the First Gulf War, sparked by Saddam Hussein’s misguided decision to invade Kuwait followed by the American-led coalition’s lightning campaign to liberate it. By contrast, the wars in Iraq and Afghanistan started on spurious grounds and concluded with self-inflicted failures. Are Operations Epic Fury and Roaring Lion destined for failure—contemporary examples of historian Barbara Tuchman’s The Guns of August and The March of Folly—or will they succeed in degrading or perhaps overthrowing the heinous Iranian regime? The following fateful days will tell.