When he was sworn in 15 years ago, Barack Obama had many goals. One of them was to not be George W. Bush, with his Manichean mentality about the world. Obama was determined to undo the damage done by Bush’s mistakes, like lumping Iran, North Korea, and Saddam Hussein’s Iraq into an “axis of evil” despite the differences in their outlooks and motivations. Hence one of the most noteworthy sentences in his 2009 inaugural address:
“To those who cling to power through corruption and deceit and the silencing of dissent, know that you are on the wrong side of history, but that we will extend a hand if you are willing to unclench your fist.”
There were implications for U.S.-Iran relations: American disagreement with Tehran’s domestic authoritarianism need not preclude cooperation in certain cases. All Iran had to do was be reasonable and stop doing destructive things, like backing terrorists throughout the Middle East. And give up its nuclear weapons program.
In 2015, when the U.S., Iran, and five other countries forged the Joint Comprehensive Plan of Action (JCPOA), I thought Obama was vindicated. I had supported him in the 2008 election, and as I watched his inauguration, I shared the hopes of liberals and progressives around the word that the U.S. had moved toward a more sensible foreign policy. By opting for sanctions on Iran rather than strikes, Obama had forced Iran to negotiate, halting its quest for nukes. I spent the next eight years defending the JCPOA, as Republicans (and more than a few Democrats) condemned it and Donald Trump rejected it in favor of “maximum pressure.” Surely, I thought, Obama’s prudence had made the world safer.
Then came October 7, 2023, when Hamas carried out the single largest massacre of Jews since the Holocaust. As the world began to recover from its shock, and Israel began its fully justified military campaign in Gaza, my thoughts turned to the men in Tehran who had armed the barbarians of Hamas for many years. Had it been a mistake to give them any concessions at all? Had Obama’s strategy of extending a hand, hoping Iran’s fist would unclench, been fatally flawed from the start?
I do not only mean the horrors of October 7. I mean some of Obama’s major choices regarding the Middle East. To reach a deal with Iran, he made many decisions that, while they may have seemed rational at the time, made bad situations worse. For the sake of not frightening too many countries in the region, and of keeping Iran at the negotiating table, Obama empowered autocrats over the forces of decency.
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Obama rightly worried a deal with Iran would frighten Israel. Before the deal was finalized, Benjamin Netanyahu spoke to Congress, at the invitation of the Republican majority (many of whom opposed everything Obama did merely because he did it), and condemned the negotiations. But as toxic as the two leaders’ relationship got, at significant moments they were on the same page. One is U.S. funding of Iron Dame, the missile defense system that has saved many Israeli lives from Hamas rockets.
Another point of agreement concerns Egypt. Israel was never happy with the fall of the dictator Hosni Mubarak (brutal, corrupt, but committed to the Egypt-Israel peace treaty), and the electoral victories of the Muslim Brotherhood. Obama, although he had pushed Mubarak to resign, never wanted to devote much attention to the Middle East, preferring to shift focus to the Pacific. Thus, when the Brotherhood governed poorly (but democratically) and faced large protests (though many protestors would not have accepted Brotherhood rule under any circumstances), he saw no need to stand up for democracy.
In his book, The Problem of Democracy, Shadi Hamid describes how early the Obama team knew the Egyptian military was planning to overthrow President Mohammed Morsi, leader of the Brotherhood-affiliated Freedom and Justice Party. Months before the July 2013 coup, they knew something was up. U.S. officials had chances to warn General Abdel Fattah el-Sisi and his fellow plotters not to oust their freely and fairly elected government. They could have used U.S. military aid - over a billion dollars a year - as leverage, threatening to cut them off unless they respected democratic outcomes. They could have forced the generals to back down.
Instead, the U.S. accepted the coup. An anti-Islamist autocrat in Cairo not only made Israel feel safer (Netanyahu has gotten along with Sisi far better than with Morsi), but also seemed easier for America to deal with. As Obama infamously remarked, “All I need in the Middle East is a few smart autocrats.” A reliable partner in Egypt was one less distraction from negotiating with Iran, even if that partner massacred protestors and filled his prisons with opponents.
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In August 2011, Obama called for Syrian dictator Bashar al-Assad to resign. Assad had responded to protests against his rule with swift and brutal force, leading Syrians who sought a just and accountable government to take up arms. Already that year, Obama had pushed Mubarak out, and had led NATO’s intervention in Libya to halt Muammar Qaddafi’s massacre of subjects seeking to end his decades of tyranny. While he did not explicitly promise to aid Syria’s rebels, the fact the American president took their side with his words gave them hope he might support them with military force.
Assad, however, is an ally of Iran. If he fell from power with American assistance, the Iranians would be less likely to negotiate over their nuclear program. That was surely one thing on Obama’s mind when he opted not to punish Assad for using chemical weapons against Syrian civilians.
Even if an Iran deal had never been a priority for Obama, it’s possible he still would not have intervened in Syria. He may still have shared many Americans’ desire to turn away from the Middle East. But his pursuit of a deal surely made it less likely he would strike back against Assad’s cruelty. In part because of Obama’s desire to sway Iran away from its nuclear ambitions, he allowed their ally in Damascus to get away with massacring 1,400 of his own people with chemical weapons.
Subsequent events provide reasons to think Obama made the wrong choice. Although he and Vladimir Putin reached an ostensible deal to remove Syria’s remaining chemical weapons, Assad has repeatedly used such weapons since 2013. Instead of a group like the Free Syrian Army, the role of primary alternative to the Assad regime was played by the Islamic State - who Assad supported to make it look like he was the only man standing in the way of a jihadist takeover of Syria.
In 2015, Putin dispatched his own forces to help Assad, since when Russian planes have repeatedly bombed civilian hospitals with no military value. Russia’s ruler also benefitted from the massive flow of Syrian refugees into Europe his brutality helped produce, sitting back and watching right-wing politicians and movements play on Western fears. He wanted to resolve another distraction from Iran negotiations, but Obama’s decision was followed by a long-running disaster.
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After Israel, Saudi Arabia is the Middle Eastern country with the most to fear from Iran’s wielding of power throughout the region. It is possible to see Crown Prince Mohammed bin Salman as a progressive ruler, pulling his medieval kingdom kicking and screaming into the 21st century. And yes, reducing a country’s reliance on oil exports and allowing its women to drive are positive steps, even if the man taking them keeps his regime thoroughly authoritarian. But domestic policies are not the only measure of a ruler’s benevolence or malevolence. His foreign policies matter, too.
MBS has been a destabilizing figure in the Middle East. During the Libyan civil war of 2014-2020, when Field Marshal Khalifa Haftar attempted to overthrow the United Nations-recognized government in Tripoli, Saudi Arabia was one of the countries backing him. Since 2015, MBS’ kingdom has been engaged in a devastating war in Yemen. All the while, the U.S. has armed Saudi forces, including under deals reached with Obama.
The U.S. and Saudi Arabia share legitimate security interests. Iran has been even more destabilizing than Saudi Arabia, with its support for violent groups across the region: Hamas, Hezbollah, the Houthis, proxies attacking U.S. troops in Iraq. Confronting Iran is a reasonable priority for Washington and Riyadh to cooperate on. Nonetheless, had Obama not been so gung-ho on an Iran deal, he might have felt at least some inclination to rein in Saudi Arabia’s more destructive tendencies.
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Barring a use of military force decisive enough to prevent it, Iran will probably develop a nuclear weapon. And even if some combination of the U.S., Israel, and Arab countries launch such a strike, there is no guarantee it will completely destroy Iran’s nuclear infrastructure. As Michael Eisenstadt of the Washington Institute for Near East Policy wrote last October:
“Even if a military strike remains a viable option, it is likely to yield only modest benefits. Bombing nuclear reactors (as Israel did in Iraq in 1981 and Syria in 2007) may buy up to a decade of delay; bombing a dispersed and hardened centrifuge program that can be quickly reconstituted would probably buy much less time. Iran will almost certainly rebuild — perhaps in secret and possibly after expelling United Nations inspectors — and it might abandon its hedging strategy after a strike and go for a nuclear bomb. For this reason, follow-on strikes might be necessary months or years down the road — and again after that.”
Would the U.S. and Israel have been better off allowing Iran to get nukes, deterring it from using them with a promise to obliterate Iran with their own nuclear weapons? Should Obama have led a coalition in destroying Iran’s nuclear program while it was much less developed? While it is possible to imagine both good and bad results from either choice, it is also possible to imagine a better U.S. approach to the Middle East during the Obama years - more defense of democracy, less tolerance for the brutality of dictators. Iran’s rulers may be on the wrong side of history, but Obama’s determination to pull them in the direction of progress led him to condone harshly retrograde actions by other powerful men.