How Months of Miscalculation Led the U.S. and Iran to the Brink of War

WASHINGTON — In late September, a plane carrying senior Iranian officials touched down in Abu Dhabi, the gleaming capital of the United Arab Emirates.

The Middle East had witnessed a summer of violence, and a meeting with the Iranians was part of a quiet strategy by Emirati leaders to defuse the tension. The small but powerful Persian Gulf nation wanted to broker a separate peace — avoiding violence that could shatter its decades-long effort to present itself as a modern, stable oasis in a volatile region.

But the meeting set off alarms inside the White House, where officials learned about it only after reading reports from U.S. spy agencies. The Emirati government, a stalwart ally that had long pushed for a hawkish American approach toward Iran, was in secret talks with Iranian officials. National Security Council officials met to discuss the implications: A united front against Iran — carefully built by the Trump administration over more than two years — seemed to be crumbling.

The episode came in the midst of a nine-month period that shook up the United States’ already combustible relationship with Iran — beginning with the Trump administration’s escalation of sanctions and culminating with the two powers in a direct military confrontation on the brink of wider and bloodier conflict.

The chess match continues, with little evidence that either has a sense of the other’s next move, but with the prospect of an American president newly constrained on Iran policy. The Senate passed a resolution Thursday requiring congressional sign-off for future military actions against Iran — a move President Donald Trump has said he would veto.

What happened over the past several months, based on interviews with officials from the United States, Iran and other Middle Eastern countries as well as outside analysts, is a story of miscalculations by both sides and of violence that spilled into nations across the Middle East — from Syria to Saudi Arabia to Iraq.

The Trump administration escalated a campaign of financial warfare — so-called maximum pressure — to suffocate Iran’s economy in hopes of forcing its government back into negotiations over its nuclear program and its military operations throughout the region. Instead, Iran lashed out with brazen attacks on oil installations in the Saudi Arabian desert, tankers docked off the Emirati coast and American forces in Iraq.

The decision by Trump to authorize the killing of Maj. Gen. Qassem Soleimani, Iran’s most powerful military commander, might ultimately deter future Iranian aggression. Yet a recent CIA analysis concluded that Iran, while struggling to continue funding its military activities under American sanctions, appears no closer to entering direct talks over its nuclear program, according to U.S. officials familiar with the assessment.

Israeli intelligence officials have also determined that the escalating tensions have made Iran only more determined to gain a nuclear weapon, and to take concrete steps toward amassing enough nuclear fuel to build one.

U.S. officials continue to defend the “maximum pressure” campaign, as Secretary of State Mike Pompeo did last month during a combative interview with NPR. He said that the United States had “raised the cost” for Iran’s military actions around the Middle East.

“This is beginning to place real choices in front of the Iranian regime,” he said.

But the fissures in the American-led anti-Iran coalition, exemplified by the secretive Emirati-Iranian talks, have dimmed a vision of a realignment in the Middle East long advocated not only by Trump, but also by the leaders of the Arab states in the Persian Gulf and Prime Minister Benjamin Netanyahu of Israel. In that vision, Israel and certain Sunni countries gain supremacy over Iran, the world’s largest Shiite-majority state.

Iranian officials also miscalculated, believing that after a series of escalatory military operations — the tanker attacks, the shooting down of an American drone, the Saudi oil strikes, rocket attacks on bases in Iraq by Iranian-backed militias — Trump would refrain from responding consequentially. Instead, he made the startling decision to authorize the killing of Soleimani.

“There were dueling perceptions both in Tehran and in Washington that the other side was a paper tiger,” said Karim Sadjadpour, an Iran expert at the Carnegie Endowment for International Peace.

The explosions happened in rapid succession.

In the predawn darkness on May 12, mines placed by naval operatives suspected to be members of Iran’s Revolutionary Guard blew holes in four oil tankers anchored in the Gulf of Oman, not far from the Strait of Hormuz, the narrow waterway through which 20% of the world’s oil flows.

Some Persian Gulf nations were hesitant to publicly finger Iran in the attacks, and Tehran denied playing a role, but the United States, Israel and European nations eventually said they had evidence proving Iran’s culpability.

The attacks came just days after the Trump administration implemented draconian new economic sanctions, which prohibited the five largest buyers of Iranian oil from future imports. When he announced the new sanctions, Pompeo said the goal was to choke off Iran’s oil exports. “We’re going to zero across the board,” he said.

Some inside the Trump administration pushed for even more punishing sanctions, even as the president’s national security adviser at the time, John Bolton, remained firm in his view that nothing short of “regime change” in Iran was an adequate outcome for security in the region.

Not long after, Israel’s Mossad intelligence service delivered a stark warning to officials in Washington about potential attacks by Iran or Shia militia groups it supports, both on U.S. forces in Iraq and against Arab states hostile to Iran, namely Saudi Arabia and the Emirates. The aim of the latter attacks, according to one person familiar with the Israeli intelligence, was to hike up the price of oil to exert pressure on the United States to ease its economic sanctions on Iran.

According to analysts and Western intelligence officials, Iran’s attacks carried an unmistakable message: If we cannot export oil, then we will not let you do it either. Iran’s response to the Trump administration’s “maximum pressure” campaign was to enact a pressure campaign of its own. Another prong of the military campaign was an escalation of cyberattacks against the United States and its allies in the Middle East. Beginning in May — just after the United States announced the new oil sanctions — and continuing through the end of the year, Iran cyberattacks on American entities doubled in comparison to earlier in 2019, according to Lotem Finkelstein, head of cyberthreat intelligence at Check Point, an Israeli cybersecurity company.

Iran had devised a strategy with two tracks, though it publicly acknowledged only one: a diplomatic outreach led by its foreign minister, Mohammad Javad Zarif, who had gained world attention as the lead Iranian negotiator in the 2015 nuclear deal. The second, led by Soleimani, used Iranian and proxy forces to foment violence across the Middle East and try to exact a cost on supporters of the Trump administration’s Iran policy.

The two men met once a week for breakfast to coordinate, Zarif said during a recent interview with Iranian state television. Before and after every trip to a capital of strategic importance like Moscow, Zarif said, he would meet with the general — first to get advice, and later to debrief him.

“Iran’s policy toward U.S. has been a combination of hardball military policy” mixed with a strategy of “softball through the foreign ministry,” said Ahmad Dastmalchian, an Iranian diplomat who was the country’s ambassador to Lebanon and Jordan.

Other attacks followed, including a missile fired by Revolutionary Guard air force units downing an American spy drone patrolling the Strait of Hormuz in June. Trump’s advisers pushed him to order a retaliatory strike which he did — but then reversed himself just hours before the strike.

Despite the attacks, Trump administration officials still believed that the sanctions were constraining the Iranian economy strongly enough to force a change of thinking in Tehran.

Plummeting oil revenues appeared to be prompting Iranian leaders to dial back funding for military operations around the Middle East. Many inside the White House believed that the economic pain was so great that Iran would, by year’s end, be willing to negotiate over its nuclear program in exchange for sanctions relief. Some close U.S. allies disagreed, including the British government, which maintains an embassy in Iran and has long held that economic pressure alone would not bring Iran into negotiations over its nuclear program. Several times last year, Britain’s ambassador to Iran, Robert Macaire — a public critic of the American policy — traveled to Washington to meet with U.S. intelligence officials and diplomats to give an assessment of the views of leaders in Iran.

Even some former Trump administration officials said that the White House’s position betrayed a misunderstanding of Iran’s leadership — born from a paucity of intelligence and direct contact with Tehran.

“We don’t have a lot of knowledge of Iran’s decision-making,” said Kirsten Fontenrose, who worked on Middle East policy at the National Security Council at the beginning of the Trump administration. “The expectation that they would come to the table was not what people who actually talk to Iranians were saying.”

In August, Eshaq Jahangiri, first vice president of Iran, gathered advisers in his office to discuss a new strategy for dealing with the Americans, according to one person who attended the meeting and another with knowledge of it.

If Trump was seeking a more comprehensive deal than the nuclear agreement he left in May 2018, the Iranians concluded, they might consider entering discussions as long as Iran extracted a firm guarantee of sanctions relief from the United States.

But even as Iran weighed renewed diplomacy, its military provocations persisted. In mid-September, Iran hit Saudi Arabia, a powerful U.S. ally, in a coordinated attack of drones and cruise missiles that set two oil-processing facilities ablaze. Both Iran’s decision to attack Saudi Arabia — and the military capabilities on display during the attack — surprised Western intelligence officials.

“It’s talking about talks but then stepping back and then putting pressures at different levels,” said Ariane M. Tabatabai, an Iran expert at RAND Corp. “They are trying to get the U.S. to see the high cost of pressuring Iran, both economically and militarily.”

In the Saudi attacks, many experts saw a careful Iranian strategy of escalation based on a conclusion that Trump had no stomach for potentially deepening U.S. involvement in the Middle East.

The strikes briefly sent oil prices skyrocketing, and once again Iran hard-liners in the White House urged Trump to retaliate militarily. Instead, he chose to deploy thousands more troops to Saudi Arabia and bolster the U.S. military presence elsewhere in the region.

The moves were part of a pressure campaign “to deprive the Iranian regime of the money that it needs to destabilize the Middle East” and to “bring Iran to the negotiating table,” Brian H. Hook, the State Department’s special representative for Iran, said at the time.

Such rhetoric was losing its impact in the Middle East, where several allies came to question the Trump administration’s commitment to defending them against Iran.

The Emiratis began their secret talks with Iran after concluding they could play a unique role lowering temperatures and that they had little confidence in the Trump administration’s approach to Iran, according to American and other Western officials. They were also dismayed by the firing of Bolton, a longtime Iran hawk.

The Saudis also explored a diplomatic breakthrough with Iran using Iraqi and Pakistani intermediaries. According to several Iranian diplomats and members of the Revolutionary Guard, Soleimani played a behind-the-scenes role setting up discussions in both gulf kingdoms.

The anti-Iran alliance that the Trump administration had tried to build was faltering. During a trip to Israel in October, Pompeo went by motorcade to a fortress in north Tel Aviv, the headquarters of the Mossad. There, he received a briefing from Yossi Cohen, the Mossad chief, about the Israeli assessment of the Revolutionary Guard’s recent military activities.

Cohen said that Iran was achieving its primary goal: to break up the anti-Iran alliance, according to one intelligence official in the Middle East.

By then, Israel had spent months escalating strikes against Iranian forces and their proxies throughout the Middle East and trying to keep the Trump administration from going wobbly on Iran.

In an interview with The Times last year, Netanyahu defended the Israeli operations and expressed no regrets for pressing Trump to back the Israeli escalation.

“If it is possible to recruit the most powerful country in the world onto our side, why should we fight alone?” he asked. “If I can harness a world power against Iran — which aims to annihilate us — why not?”

The new year brought a confrontational exchange on Twitter — Trump’s favorite way to communicate.

Violence in Iraq had been building for days, leading to the death of an American contractor and fears that Iran-backed protesters would storm the U.S. embassy compound in Baghdad.

“Iran will be held fully responsible for lives lost, or damage incurred, at any of our facilities. They will pay a very BIG PRICE! This is not a Warning, it is a Threat,” Trump tweeted on New Year’s Eve. “Happy New Year!”

Hours into 2020, Iran’s supreme leader responded with a taunt.

“You can’t do anything,” Ayatollah Ali Khamenei wrote on his English-language Twitter account. He added: “If you were logical — which you’re not — you’d see that your crimes in Iraq, Afghanistan … have made nations hate you.”

Two days later, Soleimani was dead — killed in a drone strike ordered by Trump.

Nine months of escalation, misjudgments and heated rhetoric had led to the president’s decision, which stunned both his own military advisers as well as top officials in Tehran.

“It was clear that Iran didn’t expect Trump to retaliate in any meaningful way,” said Sadjadpour, the Iran expert.

The killing prompted Iran to take a step it had long avoided: a direct and overt strike against the U.S. military. Four days after Soleimani was killed, Iran fired more than a dozen missiles at two American bases in Iraq. More than 100 U.S. soldiers were injured, but no one was killed, and Trump and his advisers believed the United States had gotten the better of the exchange.

In the weeks since, they have insisted that their strategy is working, that the steady squeeze of “maximum pressure” will force Iran to yield to their demands. But, at least publicly, Iran remains defiant and wedded to brinkmanship tactics over its nuclear program and regional military influence.

Hours after Iranian missiles landed on the U.S. bases in Iraq, Khamenei vowed that “harsh revenge” was just beginning. “The United States’ corruptive presence in the region must come to an end,” he told a large crowd in Iran’s holy city of Qom, adding that Iran would not rest until it accomplished that goal.