During the evening of June 20, 2019, President Trump pulled back air strikes on three Iranian targets that could have killed as many as 150 people. Trump tweeted that the operation was called off because it wasn’t a “proportionate” response to Iranian forces bringing down an unmanned US surveillance drone several days earlier.

“The planes were leaving” when the president called off the mission, according to a senior Trump administration official.

Trump tweeted “10 minutes before the strike I stopped it.” Trump pulled back from the brink of a much larger confrontation with Iran that was advocated by Bolton, who, like a number of hawks in recent American history, hadn’t served in any wars and had avoided service in Vietnam by taking a deferment while he was attending Yale. Yet Bolton hadn’t met a war he didn’t love.

It wasn’t quite John F. Kennedy adeptly managing the Cuban Missile Crisis, but it was one of the better moments of Trump’s presidency since it stopped an escalatory set of responses that could have embroiled the United States in a shooting war with Iran.

Such a potentially lethal strike also surely would have needed, at an absolute minimum, congressional buy-in, and more properly it would have needed an actual congressional resolution for the use of force. US presidents had sometimes disputed Congress’s authority over military strikes, but congressional approval was how things should work, according to the War Powers Act of 1973. And Trump had neither congressional buy-in nor an authorization for the use of force for a conflict with Iran.

An escalatory strike of this scale could also have posed serious risks to Americans in the Middle East. Unlike the Syrian regime against which Trump launched air strikes in 2017 and 2018, Iran had the capacity to launch significant retaliatory operations across the Middle East. Iran and its proxies had major presences in Lebanon, Iraq, Syria, and Yemen. Iran also had thousands of missiles with ranges of up to 1,500 miles that could hit targets around the region, including Israel, and could reach as far as southeastern Europe. The more hard-line elements in Iran could easily unleash their forces or proxies against American troops in both Iraq and Syria or against American commercial targets around the Middle East.

Iran also wasn’t Syria, where Trump had launched the strikes in 2017 and 2018 after the Syrian regime used chemical weapons against its own people. Those strikes enforced a significant international norm against the use of chemical weapons and had considerable support around the world. Indeed, the British and the French both participated in the 2018 strikes.

There also would have been scant support for strikes against Iran by America’s European allies, who supported the Iran nuclear deal, because the Iranians had been sticking to the terms of the agreement. The International Atomic Energy Agency had repeatedly certified that Iran had stuck to the terms of the nuclear deal. Yet, less than a month after Bolton became national security adviser, the US pulled out of the Iran deal.

Trump had largely created the crisis with Iran by pulling out of the deal in the spring of 2018 and imposing tough new sanctions on the Iranians with no real Plan B for what would come next, once the Iranians started pushing back against the sanctions that were crippling their economy.

In June 2019, Iran responded to the new US sanctions by threatening that it would start pulling out of parts of the nuclear deal. Around the same time, US officials briefed reporters about intelligence suggesting Iran or its proxies were planning to attack American forces in Iraq and Syria or at sea.

Bolton ordered up military options that were briefed to top Trump national security officials that called for as many as tens of thousands of American troops to deploy to the Middle East if Iran attacked American targets in the region or resumed work on its nuclear weapons program.

In recent weeks, Bolton had also pushed for a coup in Venezuela against the socialist strongman president Nicolás Maduro. The US-backed coup attempt fizzled. Trump blamed Bolton for the botched coup. Trump said that he actually moderated the bellicose Bolton: “I’m the one who tempers him, which is OK. I have John Bolton and I have people who are a little more dovish than him.” When Trump met with Kim Jong Un for the third time at the DMZ to discuss North Korea’s nuclear program, along tagged Jared and Ivanka Kushner, and Tucker Carlson. Meanwhile, Bolton, who had spent much of his professional career focused on arms control issues, went on a previously scheduled trip to . . . Mongolia.

Given the amount of turnover in his cabinet, Trump couldn’t get rid of Bolton immediately, but he started thinking about other candidates to be his national security adviser. Trump was intrigued by Fox News talking head Colonel Douglas Macgregor, who had been H. R. McMaster’s superior officer during the legendary Battle of 73 Easting during the first Gulf War and like McMaster had also obtained a doctorate. Unlike McMaster, Macgregor was an extreme skeptic about American military interventions in the greater Middle East, appearing on Fox to rail against the “globalist elite” on Capitol Hill and at the Pentagon and State Department who were purportedly pushing for the continuation of the Afghan War. Macgregor also appeared on Fox strongly opposing any kind of conflict with Iran.


The enemy always gets a vote in any conflict. The Iranian deep state—the Islamic Revolutionary Guard Corps and its elite Quds Force—as well as Iranian proxies around the Middle East started fighting back to signal their anger with the Trump-imposed sanctions. In May 2019, two Saudi oil tankers and two other ships were attacked in the Strait of Hormuz in the Persian Gulf. US intelligence assessed that Iran was behind the attacks. Oil facilities in Saudi Arabia were also attacked by armed drones. Houthi rebels in Yemen—armed with Iranian missiles—launched attacks at an airport in Saudi Arabia, wounding twenty-six and sending a clear message that Iran could turn the heat up on the Trump administration’s close ally, Saudi crown prince Mohammed bin Salman.

The Iranian regime also understood that Trump was quite sensitive to the price of oil, which tended to spike whenever tensions rose in the Middle East. Oil prices jumped to over sixty-four dollars a barrel after the Iranians shot down the US drone.

As a result of the increasing tensions with Iran, Bolton announced that the United States was deploying a carrier strike group and a bomber task force to the Middle East and the Pentagon deployed a total of 2,500 more troops to the Middle East. But the story got more complicated because Trump then sent mixed messages regarding his true intentions. He said he wanted to talk to the Iranians and he also tweeted that a war with Iran would be “the official end of Iran.” After the US drone was shot down, he tweeted, “Iran made a very big mistake!” Trump approved the strikes against Iranian missile batteries and radars and then he abruptly called off the operation.

The new round of US sanctions more than halved Iran’s oil exports, its key revenue source. As a result, Iran had to reduce its support for key regional proxies such as Lebanese Hezbollah, forcing the organization to cut the salaries it paid to its fighters and to withdraw some of its troops from Syria, as well as to reduce spending on Al-Manar, its TV station in Lebanon. A key goal of Trump’s “maximum pressure” campaign against Iran—forcing Iran to reduce its support for its proxy forces in the Middle East—had started to work.

The sanctions were also putting considerable pressure on Iranian officials to suggest renewed discussions about their nuclear program. Iran’s foreign minister Mohammad Zarif told reporters in New York on July 18, 2019, that in exchange for the lifting of the sanctions, Iran would allow international inspectors greater latitude to inspect its nuclear program.

Zarif didn’t have a huge amount of juice with the mullahs who actually ran the show in Iran, but Iran’s hard-line former president, Mahmoud Ahmadinejad, certainly did. Around the same time that Zarif made his offer, Ahmadinejad told the New York Times, “Mr. Trump is a man of action. He is a businessman and therefore he is capable of calculating cost-benefits and making a decision. We say to him, let’s calculate the long-term cost-benefit of our two nations and not be shortsighted.” This came a month after Trump had said he would speak to the Iranians with “no preconditions.”

Of course, there were plenty of reasons to be concerned that the confrontation with Iran could easily end in a deeper conflict instead of at the negotiating table. Iran announced in July 2019 that it was breaching the terms of the nuclear deal by enriching uranium beyond the 3.67 percent purity allowed by the agreement, enriching it above 4.5 percent. This was still a very long way from the 90 percent purity that would be needed for a nuclear weapon, but it was a small step down the road to reactivating Iran’s nuclear weapons program, the program that Trump had repeatedly said he would never allow.

The same day that Zarif was telling reporters in New York that he was ready to parley, Trump announced that the US had brought down an Iranian drone that was flying too close to the USS Boxer in the Strait of Hormuz. The Iranians denied it was one of their drones. The following day, the Iranians seized a British oil tanker that was cruising in the Strait of Hormuz.

The brinkmanship between Iran and the United States and its closest allies seemed likely to produce some kind of incident that could lead to escalatory responses on both sides. At the same time, could Trump be pulling off what he had always wanted, which was a new set of negotiations for a new deal with Iran? If so, this would truly be a “Nixon goes to China” moment for the Trump administration, which was already talking to both the North Koreans and the Taliban. Perhaps the Iranians and the Americans would follow Churchill’s admonition “To jaw-jaw is always better than to war-war”?