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activities in the region. The embargo undermined Iran’s moderates, whose reforms were already under attack from Khamenei and his supporters in parliament. By the end of Khatami’s second term, a deep political rift had opened between Iran’s moderates and conservatives.⁴⁵

      In 2001, the Sept. 11 terrorist attacks led to a short period of cooperation between Iran and the United States. Iran had long opposed Afghanistan’s Taliban regime and the al Qaeda terrorists it harbored, both strict Sunni fundamentalist groups who regarded all Shiites as heretics. Tehran condemned the 9/11 attacks and quietly provided special forces to help the U.S. military topple the Taliban.⁴⁶ Iran also helped the United States form a new pro-Western Afghan government.⁴⁷

      But Republican President George W. Bush ignored Tehran’s assistance and in his first State of the Union speech in 2002 lumped Iran with Iraq and North Korea as part of an “axis of evil.” He threatened U.S. military action to block their nuclear programs. But Iran persisted, volunteering to arm, train and support 20,000 Afghan troops under a U.S.-led program. American officials never responded to Iran’s offer.⁴⁸

      After the U.S. invasion of Iraq in 2003, Iran—fearing it was next—made a sweeping offer to address the issues dividing Washington and Tehran. But the Bush administration did not respond to that offer, either.⁴⁹ Instead, the United States and Israel launched a cyberattack on Iran’s nuclear program, using the Stuxnet virus to destroy scores of centrifuges used to enrich uranium.⁵⁰

      Shifting Policy

      In 2005, Mahmoud Ahmadinejad, the hard-line mayor of Tehran, was elected president of Iran. As U.S. troops became bogged down by insurgencies in Iraq, Iran shifted policy and threw its support behind Iraqi Shiite militias fighting the Americans. Over the next four years, the militias killed hundreds of U.S. troops.

      When Democratic President Barack Obama took office in 2009, he reached out to Iran in a broadcast. “My administration is now committed to diplomacy that addresses the full range of issues before us,” Obama said.⁵¹ The top issue was Iran’s nuclear program, which U.S. and Israeli officials suspected was aimed at developing a nuclear weapon.

      But Israel threatened Obama’s diplomatic effort, letting the administration know it planned to bomb Iran’s nuclear infrastructure before it became too advanced. Obama repeatedly dispatched senior U.S. officials to Jerusalem to argue that an attack would spark another Mideast war that inevitably would involve the United States. But Israeli Prime Minister Netanyahu argued that Iran’s response would be limited. Besides, he added, an Israeli strike would not only derail Iran’s nuclear program but also spark the overthrow of the Tehran regime.⁵²

      The administration did not know whether Netanyahu was bluffing. So as U.S. spy satellites watched Israel openly prepare for an attack, Obama chose another strategy: secret negotiations with Iran. In late 2010, two top White House aides flew to Oman, where they quietly hammered out a framework for negotiations with Iranian officials representing Khamenei.⁵³

      In 2013, prospects for better relations with Iran brightened after moderate Rouhani was elected president and indicated during a trip to the U.N. General Assembly that his government was ready to engage with the United States.⁵⁴ A few days later, Secretary of State John Kerry and Iranian Foreign Minister Zarif met to discuss how to follow up on the framework agreement reached in Oman.⁵⁵

      Their meeting launched intense negotiations for a nuclear accord between Zarif and Kerry and the foreign ministers of Russia, China, Britain, France, Germany and the European Union. On July 14, 2015, after two years of talks, they signed the Joint Comprehensive Plan of Action (JCPOA), under which Iran agreed to curtail its nuclear program in return for relief from international sanctions. The U.N. Security Council endorsed the deal, giving it the imprimatur of international law.⁵⁶ The United States, however, kept its non-nuclear sanctions in place.

      Israel and Saudi Arabia castigated the accord, noting that it failed to address non-nuclear threats, such as Iran’s ballistic missile program and its support for proxy forces across the region. Trump adopted that view as he campaigned for the 2016 Republican presidential nomination and pledged to withdraw the United States from the agreement if elected.

      Trump made good on that promise in May 2018, despite repeated U.N. certifications that Iran was in full compliance with the agreement’s provisions. Six months later, Trump reimposed crippling economic sanctions on Iran, reigniting the hostility and distrust that had poisoned U.S.-Iran relations for nearly 40 years.

      Current Situation

      Escalating Standoff

      Washington and Tehran are now locked in an escalating standoff that could explode into a major Middle East war unless the two sides can reach a diplomatic solution, warn many former officials and regional experts. But the chances of negotiations taking place anytime soon seem remote.

      For now, both countries, as well as Iran’s rival Saudi Arabia, have stepped back from the brink, sobered by September’s suspected Iranian attack against Saudi oil facilities. But Trump’s overall strategy of strangling Iran’s economy remains in place, as has Tehran’s unyielding resistance. If those policies persist, a military confrontation is more likely than not, observers say.

      “That’s why we’ve got to be very, very careful,” says former Ambassador Crocker. “The law of unintended consequences is always in force in the Middle East.”

      In early 2019, Iran hoped the Europeans would maintain the economic investments and other benefits promised by the nuclear deal and also sought to gain leverage by gradually reviving its nuclear program, in deliberate violation of the 2015 accord. The breaches could be reversed if the Europeans came through, Tehran said. But the U.S. sanctions proved too intimidating for the Europeans to move ahead with the plan for a special trade-financing mechanism using barter instead of U.S. dollars.

      U.S.-Iran tensions have intensified significantly since April, when the Trump administration refused to renew waivers that allowed eight countries to continue buying Iranian oil.⁵⁷ The waivers had gone to Tehran’s biggest customers—including China, India and Japan—whose oil purchases had helped insulate Iran’s economy from the sanctions. With the cancellation of those waivers, the administration signaled its intention to shut down Iran’s oil sector and maximize Iran’s pain.

      “We’re going to zero across the board,” said Pompeo as he announced the end of the waivers. “How long we remain there … depends solely on the Islamic Republic of Iran’s senior leaders.”⁵⁸

      Despite a subsequent plunge in Iran’s oil sales and severe economic hardship for ordinary Iranians, the sanctions have had no apparent effect on Tehran’s national security policies, according to Iran experts. “On the contrary, instead of Iranians backing down, coming to the negotiating table and begging on their knees for mercy, they have counter-escalated in almost every area of contention with the United States,” says Iran expert Parsi.

      Following Trump’s withdrawal from the JCPOA last year, Tehran has gradually breached restrictions on Iran’s nuclear program in an effort to pressure the accord’s European signatories to come up with the JCPOA’s promised economic benefits. In the most recent breach, President Hassan Rouhani said in November that Iran would accelerate its nuclear enrichment activities by injecting uranium gas into centrifuges at its underground Fordow facility. Under the JCPOA, Iran agreed to halt nuclear enrichment at that facility and use it for research. Meanwhile, Iran said it added dozens of advanced centrifuges to its uranium enrichment efforts, shortening the time needed to produce enough highly-enriched nuclear fuel for a bomb.⁵⁹

      Iran experts say Tehran also continues to support its Middle East proxies, as evidenced by the Sept. 14 drone-and-cruise-missile attack on Saudi oil facilities and Iran’s recent moves to enhance the range and accuracy of missiles it has given Hezbollah, the Houthis and the Iraqi Shiite militias. “Even in the worst of times economically, those efforts are not underfunded,” says Crocker. With an unpredictable Trump at the helm

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