America in the Middle East: learning curves are for pussies.
—Jon Stewart, The Daily Show, June 2, 2015

In January 2017, following Donald Trump’s inauguration, his national security staffers entered their White House offices for the first time. One told me that when he searched for the previous administration’s Middle East policy files, the cupboard was bare. “There wasn’t an overarching strategy document for anywhere in the Middle East,” the senior official, who insisted on anonymity, told me in a coffee shop near the White House. “Not even on the ISIS campaign, so there wasn’t a cross-governmental game plan.”

Wreckage in Arbin, eastern Ghouta, Syria, which was under siege by the Assad regime, March 27, 2018 © Ammar Al Bushy/Anadolu Agency/Getty Images

Rob Malley, President Barack Obama’s senior Middle East adviser and Harvard Law School classmate, denied the charge. “That can’t be true,” the fifty-­five-­year-­old scholar insisted when we met in his office at the International Crisis Group in Washington. “We provided comprehensive memoranda to the incoming team, though we can’t know if they read them. We definitely had a long one on Syria, on all aspects of the conflict.”

I have observed the Syrian conflict off and on since it began, in 2011, filing stories from Damascus, Aleppo, Homs, Palmyra, the Turkish border, and other zones of contention. But the story as seen from inside Syria seemed as incomplete as the Trojan War without the gods. In the conflagration’s eighth year, I flew to the Olympian heights of Washington to ask the immortals what they were doing while an estimated half million of Syria’s twenty-­three million inhabitants were dying, millions more fled the country, and some of civilization’s most precious monuments were destroyed.

The mandarins’ disclosures, along with their published memoirs and position papers, made me sympathetic to the Trump staffer’s claim that the Obama team left nothing to clarify its Syria strategy. In fact, there was no strategy. There were debates, options, discussions, anguish, orders, counterorders, and actions. In his recent book on his years as Obama’s deputy national security adviser, The World As It Is, Ben Rhodes portrayed White House deliberations as group therapy more than strategic planning. “I felt the burden on Obama,” he wrote, one of many examples of his and his colleagues’ feelings overshadowing circumstances. “He had to respond to this awful event in Syria while bearing the additional weight of the war in Iraq. . . . ” But isn’t that a president’s job?

The men and women around Obama’s conference tables and via video links claimed that, more than anything else, they wanted to do the right thing. In Rhodes’s case, anything. “Even though I had misgivings about our Syria policy,” he wrote, “I was glad we were doing something.” Obama’s strategists sought to make Syria better. As they admit now, they didn’t.

Riots between police and demonstrators in Tunis, Tunisia, January 18, 2011 © Alex Majoli/Magnum Photos

The year 2010 neared its end with the Middle East mired in stasis. The United Nations Human Development annual report for that year concluded that the Arab states suffered the world’s greatest democracy deficit, the highest number of human rights violations, and the world’s most pronounced “gender disparities in reproductive health, empowerment and labour market participation.” Arab dictators had their populations under control, while they pillaged the public purse to enrich themselves and purchase American weaponry. Palestinian–­Israeli peace was going nowhere, and Iran appeared determined to acquire nuclear weapons to match Israel’s.

But stasis shifted toward dynamism in December 2010, when the self-
­immolation of an unemployed and desperate young man named Mohamed Bouazizi inflamed Tunisia. Mass demonstrations forced the flight of President Zine El Abidine Ben Ali, inspiring similar protests elsewhere in the Arab world. “They were the heady days of the Arab Spring,” said Michael Dempsey, Obama’s deputy director of national intelligence and chief intel briefer. Citizens massed in the thousands in Egypt, Bahrain, Yemen, and Libya, exploding the myth of a supine Arab world.

The vulnerable regimes in early 2011 were in the American camp, a coincidence that the Syrian president, Bashar al-­Assad, interpreted as proof that the Arab Spring was a repudiation of American tutelage. As Russia’s and Iran’s only Arab ally, he foresaw no challenge to his throne. An omen in the unlikely guise of an incident at an open-­air market in the old city of Damascus, in February 2011, should have changed his mind. One policeman ordered a motorist to stop at an intersection, while another officer told him to drive on. “The poor guy got conflicting instructions, and did what I would have done and stopped,” recalled the US ambassador to Syria, Robert Ford, who had only just arrived in the country. The second policeman dragged the driver out of his car and thrashed him. “A crowd gathered, and all of a sudden it took off,” Ford said. “No violence, but it was big enough that the interior minister himself went down to the market and told people to go home.” Ford reported to Washington, “This is the first big demonstration that we know of. And it tells us that this tinder is dry.”

The next month, the security police astride the Jordanian border in the dusty southern town of Daraa ignited the tinder by torturing children who had scrawled anti-­Assad graffiti on walls. Their families, proud Sunni tribespeople, appealed for justice, then called for reform of the regime, and finally demanded its removal. Rallies swelled by the day. Ford cabled Washington that the government was using live ammunition to quell the demonstrations. He noted that the protesters were not entirely peaceful: “There was a little bit of violence from the demonstrators in Daraa. They burned the Syriatel office.” (Syriatel is the cell phone company of Rami Makhlouf, Assad’s cousin, who epitomized for many Syrians the ruling elite’s corruption.) “And they burned a court building, but they didn’t kill anybody.” Funerals of protesters produced more demonstrations and thus more funerals. The Obama Administration, though, was preoccupied with Egypt, where Hosni Mubarak had resigned in February, and with the NATO bombing campaign in Libya to support the Libyan insurgents who would depose and murder Muammar Qaddafi in October.

Ambassador Ford detected a turn in the Syrian uprising that would define part of its character: “The first really serious violence on the opposition side was up on the coast around Baniyas, where a bus was stopped and soldiers were hauled off the bus. If you were Alawite, you were shot. If you were Sunni, they let you go.” At demonstrations, some activists chanted the slogan, “Alawites to the grave, and Christians to Beirut.” A sectarian element wanted to remove Assad, not because he was a dictator but because he belonged to the Alawite minority sect that Sunni fundamentalists regard as heretical. Washington neglected to factor that into its early calculations.

Phil Gordon, the assistant secretary of state for European affairs before becoming Obama’s White House coordinator for the Middle East, told me, “I think the initial attitude in Syria was seen through that prism of what was happening in the other countries, which was, in fact, leaders—the public rising up against their leaders and in some cases actually getting rid of them, and in Tunisia, and Yemen, and Libya, with our help.”

Ambassador Ford said he counseled Syria’s activists to remain non­violent and urged both sides to negotiate. Demonstrations became weekly events, starting after Friday’s noon prayer as men left the mosques, and spreading north to Homs and Hama. Ford and some embassy staffers, including the military attaché, drove to Hama, with government permission, one Thursday evening in July. To his surprise, Ford said, “We were welcomed like heroes by the opposition people. We had a simple message—no violence. There were no burned buildings. There was a general strike going on, and the opposition people had control of the streets. They had all kinds of checkpoints. Largely, the government had pulled out.”

Bassam Barabandi, a diplomat who defected in Washington to establish a Syrian exile organization, People Demand Change, thought that Ford had made two errors: his appearance in Hama raised hopes for direct intervention that was not forthcoming, and he was accompanied by a military attaché. “So, at that time, the big question for Damascus wasn’t Ford,” Barabandi told me in his spartan Washington office. “It was the military attaché. Why did this guy go with Ford?” The Syrian regime had a long-standing fear of American intelligence interference, dating to the CIA-­assisted overthrow in 1949 of the elected parliamentary government and several attempted coups d’état afterward. The presence in Hama of an ambassador with his military attaché allowed the Assad regime to paint its opponents as pawns of a hostile foreign power.

Photographs of the Assad family, on a wall in Aleppo, March 2013 © Moises Saman/Magnum Photos

The State Department closed the US Embassy in Damascus in February 2012 following intelligence that the Salafist Jabhat al-­Nusra group planned to bomb it. Syrian friends told me that, before he left, Ford had urged them to defect and return as part of a post-­Assad government. Ford’s recollection differed: “I remember the next-­to-­last day of our embassy—we closed on February 6—I told the Syrian staff . . . the embassy is going to close. They said, What are we going to do? I told them, there is going to be a horrible war. There’s going to be bombs. The currency is going to plunge. I said, those of you who can, buy dollars, buy euros, any kind of foreign currency, because the lira is going to drop like Iraq. And get out if you can. I don’t remember telling any Syrian opposition to go to Istanbul.” One Syrian contact told me that the French ambassador, Éric Chevallier, had invited him to leave and come back “in two months” as part of the new order. He declined the offer.

Ford returned to Washington, where Obama’s brain trust held endless conferences to form a policy for Syria. Jake Sullivan, Vice President Joe Biden’s national security adviser, attended most of the sessions. “The question was why Qaddafi must go and not Assad,” the slim forty-­one-­year-­old Yale law professor told me in his office at the Carnegie Endowment. No one, he said, convinced Obama that attacking Assad would achieve a result better than the anarchy following NATO’s bombardment of Libya. The debates continued throughout the spring, as open warfare erupted in Syria.

“By summer,” Sullivan observed, “there was a divide within the administration, ‘principals’ versus those who worked the Syria file. Experts were more forward-­leaning; principals, more cautious.” The leading experts were Fred Hof and Robert Ford; the principals, Secretary of State Hillary Clinton and Defense Secretary Leon Panetta. Ford said, “I wrote a memo to Clinton with a copy that went to the White House—this was in June 2012—that the Al Qaeda faction is taking over eastern Syria. And the Free Syrian Army doesn’t have enough supplies, not enough money, to hold them off. If eastern Syria falls, they are going to link up with the people on the other side of the border in Iraq and create this gigantic entity.” Two years later, the Islamic State would establish its caliphate on exactly that territory.

With the principals urging caution, the Obama Administration dispatched nonlethal aid—what Ford called “food, medicines, meals ready to eat, stuff like that”—to the ostensibly moderate Free Syrian Army (FSA) faction. It also worked through a diplomatic channel with Russia. When neither produced results, a senior administration official said, “The State Department, the agency [CIA], and some in the White House began advocating for providing arms to the Free Syrian Army. That summer, [CIA Director David] Petraeus and Clinton made a pitch. The president shot it down, ‘for now.’”

Derek Chollet, who served Obama at Defense, State, and the White House, picked up the story: “And the general view was, and I think even at this point, that Assad, one way or another, he would go. And so we need to, in order to have any chance to be able to shape an outcome on the other end, we should be for it.” In the absence of doing something, Obama said something, on August 18, 2011: “For the sake of the Syrian people, the time has come for President Assad to step aside.” Where Assad sensed a plot to depose him, the opposition envisioned American–­NATO commitment, as in Libya.

Fred Hof told me, “Our view in the State Department was, fine, if this is the judgment the president comes to, that Assad should step aside, then what we should really have in place is an interagency strategy to make it happen.” Hof regretted that the White House did not develop that strategy, on the assumption that “this guy [Assad] is toast.”

Chollet described one effect of Obama’s “step aside” statement: “It raises expectations on the ground. . . . It means you’re saying they should go at the tip of a military spear.” Obama, while imposing tougher economic sanctions on Syria, was not providing the spear, “for now.” Then, Phil Gordon recalled, White House perceptions altered: “That was the evolution from skepticism and ’not really our role’ to a bit more optimism [that] maybe we can even assist this process along.” The question was, what kind of assistance? Gordon did not believe Obama had in mind “providing military material support to Arab protesters.” There was a view, he said, “It’s just, well, this is the trend, and the people overthrew their dictators in Tunisia and Egypt and Yemen. And Syria will be next. And I think it was more hope than a policy.” But that hope ignored the differences between Syria and the deposed dictatorships.

Tunisia’s tiny army was not a decisive political actor and the country had staged only one coup in its history, Ben Ali’s in 1987. Government institutions could function without him. In Egypt, Mubarak was the face—called derisively by Egyptians “la vache qui rit,” “the laughing cow”—of a military regime that could survive with any general as its figurehead. In Syria, Bashar al-­Assad was the regime. His father, Hafez al-­Assad, had come to power in November 1970 as the survivor of nearly annual military putsches in the 1950s and 1960s. At his death in June 2000, he bequeathed his son an edifice that had prevailed over thirty years of failed coup plots, assassination attempts, wars with Israel, and Islamist insurrections. To depose the son, the opposition had to undermine a fortress state to which many Syrians were loyal, or at least acquiescent.

Obama imposed economic sanctions, primarily on members of the regime’s inner circle, and he asked the Russians to pressure Assad to leave. Phil Gordon, who accompanied Hillary Clinton to meetings with the Russian foreign minister, Sergey Lavrov, said, “Lavrov would say, ‘It’s not up to us.’ . . . The Russian view was, ‘Look, we don’t love Assad. We don’t care about him, but it’s not up to us to determine Syria’s fate.’” Lavrov also warned Clinton that removing Assad would lead to chaos and jihadism. “They had a fair point in saying we didn’t have a plan for Syria if we got rid of Assad,” Gordon admitted. “And, to be honest, I don’t think we were ever in a position to convincingly say, ’No, no, no, if Assad falls, it won’t be like Iraq or Afghanistan.’ ”

In Damascus and other cities, security forces fired live ammunition at the crowds, and although the United States had sided with security forces who shot Arab demonstrators in Israel and Bahrain, its sympathies in Syria were with the protesters. Many Syrian activists argued that they should take up arms in the belief that the United States would match action to words. Others urged restraint, fearing that, force against force, they would lose. “The regime was built for this,” one young organizer told me at the time.

“The beginning of militarization had started before the end of 2011,” Fred Hof said, noting the escalation from defending demonstrators to offensive operations. The door opened wide to outside meddling. Hof said that arms from Turkey, Saudi Arabia, and Qatar—three countries whose human rights records were no better than Syria’s—to various, mainly Islamist, groupings had an unexpected consequence: “I think all of this inadvertently but quite decisively played into the hands of the regime.” The Assad regime’s strategy for dealing with civil disobedience, popular mobilization, and general strikes may have been ineffective, but the regime knew how to handle armed insurrection. And Salafist fighters terrified many Syrians who, while dismissive of Assad, did not welcome his replacement by religious fanatics with long beards. Hof said, “I’m not just talking about the entourage and members of the [Assad] family, but ordinary Syrians, Syrians I’ve known for decades, who would tell me, ‘Fred, we’re going to stick with the regime.’’’ Hof said they stuck with Assad, despite having “no illusions about the corruption, incompetence, and brutality of the regime.” Others who did not fight against the regime were the minorities—Alawis, Ismailis, Druze, Arab Christians, Armenians, and Yezidis, all of whom the jihadis wanted to eliminate—as well as Sunnis who preferred a secular dictatorship to a theocracy.

Hof pushed for supporting secular insurgents. Other officials, he told me, shared his viewpoint:

In the summer of 2012, you had the incident of Clinton, [CIA Director David] Petraeus, [Defense Secretary Leon] Panetta, and [Chairman of the Joint Chiefs of Staff Martin] Dempsey going to the president and saying, in effect, Look, Mr. President, what Assad is doing is terrible, but now we’re noticing something else. We’re noticing some Al Qaeda elements beginning to establish themselves in Syria, and what we recommend is that the United States take the lead in arming and training vetted elements of the Syrian opposition, focusing, for the most part, on officers and soldiers who had defected from the Syrian army, forces that would be able to fight in two directions—against the regime and against Al Qaeda. And the president turned that down. He turned it down.

Rebel fighters prepare to launch a grenade with a homemade slingshot in the Old City, Aleppo, 2013 © Moises Saman/Magnum Photos

In August 2012, a year and a half into the war, a question from the NBC correspondent Chuck Todd produced a portentous response from Obama: “We have been very clear to the Assad regime, but also to other players on the ground, that a red line for us is we start seeing a whole bunch of chemical weapons moving around or being utilized. That would change my calculus.” As with his call a year earlier for Assad to step aside, Obama’s chemical-­weapons declaration would haunt him. A former US ambassador to the Middle East told me, “The ‘red line’ was an open invitation to a false-­flag operation.” Robert Gates, who was the secretary of defense from December 2006 to July 2011, after leaving the department called the red line “a serious mistake” that harmed American credibility.

On August 21, 2013, poison-­gas canisters shattered the early-­morning quiet in eastern Ghouta, a populous rebel-­held suburb of Damascus. Horrifying videos showed the world children gasping for breath, victims frothing at the mouth, and discolored corpses without visible wounds. Prior to this massive outrage, there had been sporadic and small-scale use of chemical weapons by both sides, for which each side blamed the other. In Washington, the director of national intelligence, James Clapper, told Obama that the case against Assad was not a “slam dunk,” the term CIA Director George Tenet used in December 2002 to affirm that Saddam was hiding weapons of mass destruction. Nonetheless, Obama declared that Assad had crossed the red line.

“Whoever actually used chemical weapons in east Ghouta,” said a CIA analyst, “the blame went straight to Assad. He had crossed the red line, and the rebels were not the only ones who expected him [Obama] to do something about it.”

Ben Rhodes wrote that General Dempsey urged Obama to act: “Up to this point, he had argued that Syria was a slippery slope where there was little chance of success. Now he said that something needed to be done even if we didn’t know what would happen after we took action.” Obama decided to act, calling on Britain and France to join an American air and missile assault on Syria. France committed at once, but the British Parliament voted not to take part. As French and American forces prepared to strike, Obama took a walk in the Rose Garden with his chief of staff, Denis ­McDonough. Suddenly, the order went out for the warplanes to stand down.

“The next morning, there was a meeting in the Situation Room,” said Jake Sullivan, who sat in. “[Secretary of State John] Kerry, [Defense Secretary Chuck] Hagel, the principals. Samantha [Power] was on the screen. ­McDonough, [National Security Adviser] Susan Rice. Susan objected. She said, Don’t go to Congress. Obama went out later that day and gave a statement on asking Congress.” Morning in Washington was night in Syria, when I drove into Damascus. It looked as if it had been evacuated. Even the troops had gone into shelters. The capital was braced for a massive Franco-American air strike. Syrian friends feared the jihadis would overrun the capital under cover of the Western attack, until the announcement came from Washington that the raid would not take place.

A series of unscripted statements by Kerry and Lavrov led Russia to persuade Assad to acknowledge his poison-­gas arsenal, sign the Chemical Weapons Convention, and allow the Organization for the Prohibition of Chemical Weapons (OPCW) to destroy his stockpiles. When the Islamic State later overran the government’s chemical-weapons stores, they had been removed. The crisis ended, but gases including chlorine and sarin would be used again—as before, with blame placed on each side by the other. As the war escalated, at least 95 percent of the casualties resulted from conventional weapons from Russia, the United States, Saudi Arabia, Qatar, the United Arab Emirates, Turkey, and Iran that no one was obstructing.

Free Syrian Army fighters launc h a rocket-propelled grenade toward a Syrian Army position in Aleppo, February 17, 2013 © Franco Pagetti/VII/Redux.

Debate continued within the administration on what to do. Obama listened to arguments for and against no-­fly zones and safe havens. Robert Gates addressed the no-­fly zone proposal in an interview with CBS’s Face the Nation after he left office:

You know, I oversaw two wars that began with quick regime change. And we all know what happened after that. And as I said to the Congress when we went into Libya, when they were talking about a no-­fly zone, “It begins with an act of war.” And haven’t we learned that when you go to war, the outcomes are unpredictable? And anybody who says, “It’s gonna be clean. It’s gonna be neat. You can establish the safe zones. And it’ll be, it’ll just be swell”—well, most wars aren’t that way.

No-­fly zones required demolishing Syria’s air defenses, which the Russians had installed and were committed to defending. “No-­fly” also meant making targets of Russian planes in Syrian skies, risking a third world war.¹

The bleak history of safe havens in Bosnia, where civilians seeking safety were massacred while UN soldiers looked away, made their utility suspect. Safe havens and no-­fly zones, however, dominated White House deliberations. One of Obama’s Middle East advisers recalled, “Was the right approach to create safe zones? No-­fly zones? Discussions on this issue continued well into 2016. Even as late as the assault on Aleppo [by the Syrian Army and Russia in 2016], questions returned about what we could do, whether to go after the regime directly or protect the city.” I asked the adviser, “Then the decision was made not to?” He answered, “Right.”

If the Obama people were to have done something, what would it have been? An acquaintance of John Kerry’s with Mideast expertise who asked not to be named recalled Kerry telling him in 2013, “Let’s get serious. There is no more resolution to this Syrian thing without Bashar. He has to be brought in, and we have to negotiate with him.” The consultant recalled that Kerry spoke later that day to a wealthy Syrian-­British businessman, who argued that the United States had to depose Assad. The consultant saw Kerry the next day: “Kerry told me, completely oblivious to what he said before, ‘Assad has to go. As long as Assad is there, he is a magnet for terrorists.’ I said, ‘Assad is a magnet for terrorists? What is it about Assad that attracts them to fight? What about the ones in Sinai? In Mali? In Yemen? In Kenya? In Somalia? What do they have to do with Assad?’ . . . There was no policy. They were making it up as they went along.”¹

One of the administration’s more articulate Syria hawks was Antony Blinken, Obama’s deputy national security adviser and then John Kerry’s deputy secretary of state from 2015 to 2017. He recalled Obama’s reaction to every proposal to deploy troops or air power in Syria: “I think from President Obama’s perspective, when some of us would advocate to do more, take some more chances, he would regularly ask, ‘Tell me how this ends.’ No one could answer with confidence that we would not wind up on a slippery slope, getting in deeper and deeper than we intended.”

A senior Mideast adviser to Obama explained the misgivings of the administration’s anti-­interventionists:

Many in the administration were in favor of some form of intervention, perhaps targeted strikes. But there was also significant skepticism about the wisdom of direct U.S. military involvement, about the nature of the opposition, the risk of a slippery slope.

The compromise between direct military involvement and staying out was the route taken by many presidents before Obama: a covert operation to raise an insurgent army and train it in nearby countries; provide weapons, sustenance, and communications; and oversee the military campaign. It was high-risk for the locals and casualty-­free for the Americans. A senior administration official told me, “Only a few were against arming the opposition. Obama commissioned a report on the history of arming groups.”

The CIA produced a history that remains classified and which, says one of those who read it, showed “only one or two instances of successful proxy wars.” Despite the failure of the CIA’s secret wars, from Albania in the late 1940s through Angola in the 1970s and 1980s, Obama assigned the CIA to train militants in Turkey and Jordan under what is called a Title 50 program in defense of American national security.

Rebels turned up with equipment they could not have looted from the Syrian Army. Al Qaeda-­linked gangs shared the bounty, prompting Secretary of State Clinton in the summer of 2012 to fly to Istanbul, by then the unofficial capital of the Syrian opposition in exile. Jake Sullivan said that she wanted US allies Turkey, Saudi Arabia, and Qatar “to ensure the arms were provided with checks to make certain they were not going to Nusra or other terrorist groups.” He recalled her asking, “‘How are the controls implemented?’ The steps were taken, but they were incomplete.” Incomplete or non­existent, because jihadis with weapons supplied by American allies flooded Syria through the Turkish border.

Charles Lister, who has monitored insurgent groups from the beginning of the Syrian conflict and wrote The Syrian Jihad, told me, “By the summer of 2012, there was a pretty active effort on both sides of Syria’s northern and southern borders to prop up and help to create a somewhat more organized opposition movement. But the fact that Qatar and Turkey and Saudi and the UAE and Jordan were all involved, as governments, and then there were separate private networks coming out of Doha, Kuwait City, Istanbul—every single one of them was working along their own chart.” Lister estimated that at one time there were as many as fifteen hundred insurgent groups with conflicting goals and no central command. It was a recipe for failure as much as for carnage.

A major source of weapons for the Syrian opposition was Libya, which had become a twenty-­four-hour arms bazaar. It furnished TOW anti-­tank missiles and other war matériel with the help of the CIA station at the US consulate compound in ­Benghazi.² CIA director David Petraeus became so concerned that Al Qaeda affiliates were receiving the weapons that he flew to Turkey on September 2, 2012, to complain to Turkish president Recep Tayyip Erdogan. The supply chain became public after the September 11 murder of US ambassador Christopher Stevens in the Benghazi compound. Media outlets, including Fox News, reported that ships delivered TOWs, surface-to-­air missiles, and other high-­tech weaponry from Libya to the port of Iskenderun in southern Turkey. After the publicity, Washington put full blame on Qatar for running a rogue operation without US approval. “That’s bullshit,” a CIA source told me.
Rebel training became the province of US and British agents, and the Turks allocated weapons. But there was no control over fighters when they infiltrated Syria, where many joined Salafist brigades. A British trainer told me that the program was benefiting religious fanatics more than any moderate, secular oppositionists.

The TOWs from Benghazi shifted the balance on the ground in favor of the rebels, especially the better-armed and highly motivated jihadis. Assad’s tanks and helicopters were no longer invulnerable. Phil Gordon refused to discuss the issue of covert assistance, but he noted that the administration “started to publicly say in the spring or maybe June of 2013 that we were providing direct support to the opposition, including military support.” The support was a program, and the program had a name: Timber Sycamore.

Speaking in his office at Washington’s Middle East Institute, Charles Lister recalled,

Sometimes they [the insurgents] suddenly found themselves wearing nice uniforms, new camouflage fatigues. And it pretty quickly emerged that, at the end of 2012, weapons, mostly from [the] former Yugoslavia, had started to be shipped in through Amman into the south. And then some of that started to appear in northern Syria. I don’t know exactly when an open channel was established, but it wouldn’t have been any later than the spring of 2013. Certainly [by] December of 2012, those first weapons appeared in the south. And it subsequently became clear the reason why that had started was because the CIA had received clearance, I assume from the White House, to run a pretty substantial Title 50 covert program of assistance to the vetted Syrian opposition.

CIA operatives in Turkey and Jordan screened rebels to weed out fundamentalists. Vetting, however, proved futile.

The net effect was not, as Phil Gordon hoped, to “accelerate the process of Assad’s departure.” In fact, Gordon conceded, it was the opposite: “I think that what we saw was that the more we did for the opposition, the more the backers of the regime did for the regime.” Iran’s Lebanese surrogate, Hezbollah, sent more fighters from Lebanon to back Assad. The Russians came to Assad’s rescue with troops and air power, while the Iranians introduced units of Iraqi and Afghan Shias.

On the opposition side, jihadis from Chechnya, Afghanistan, Algeria, China, and Europe joined the fight. Together with indigenous fundamentalists, they reduced the FSA to irrelevance. “We didn’t have a great understanding of who was doing what on the ground,” Phil Gordon said, “and couldn’t control it. So, you would be running the risk that, almost the inevitable risk that, in a revolutionary situation, the worst guys were the ones that would take and use the weapons.” The most extreme elements, the Al Qaeda offshoots Jabhat al-­Nusra and the Islamic State, not only used the weapons but also advertised them in videos that included beheadings, the hurling of gay men off towers to their deaths, the murder of American journalists and British aid workers, and the rape of Yezidi women. Charles Lister said that “all of the opposition worked with Nusra, because they were very good on the battlefield. But what was the result of that in London and Paris and Washington and elsewhere? We began to look at the opposition like they were all jihadis.”

Gerald Feierstein, the US ambassador in Yemen before becoming deputy assistant secretary of state for Near Eastern affairs in 2013, underscored the Obama Administration’s naïveté in 2014, three years into the war: “There was a sense that the momentum was really with the opposition, the government was weak, and some hope that at least if not Bashar himself but that others within the regime might be interested in some kind of a face-­saving way to get out of a jam. But they weren’t.” Others in the administration, he said, “were saying that we should just accept that Bashar was going to stay.”

While administration officials debated, Syria descended deeper into mayhem that was driving millions out of the country and thousands to their graves. By the summer of 2015, I could no longer reach Aleppo from Damascus because of the fighting. I called Armen Mazloumian, whose family had owned and run the city’s famed Hotel Baron since 1909. He blamed the West for giving arms to the jihadis occupying the eastern half of the city. Mazloumian died shortly afterward, his health having given out amid the danger and privation of the war. How far away all that must have seemed in the cozy offices of the White House, not to mention the Kremlin, where self-­described statesmen determined the fate of Armen and the rest of Syria.

Rob Malley believes Obama’s primary motivation was humanitarian. The administration sent aid to refugees in Turkey and Jordan and deployed a ­USAID transition-and-­response team, under the name ­START, to assist local administration in parts of Syria that the regime had evacuated. The problem in Syria, though, was not humanitarian; it was political, and the political dynamics were evolving. An official who took up his post at the White House in February 2014 observed a policy too entrenched to be reversed: “The opposition backed by the US was also backed from the outset by others—Saudi Arabia, Turkey, and Qatar, whose objective clearly was to overthrow the regime and remove Iran. That is what the war quickly came to be about.”

By that stage, one faction in the administration got cold feet. Phil Gordon said, “I’ll be honest, and I’ve written about this publicly, by then I had concluded that we had a strategy that just wasn’t going to work.” Gordon said that the United States by 2015 had “a means-­ends gap. You have to change the means or the end.” His conclusion was that the United States should change the objective, because “it wasn’t realistic to get rid of Assad. I didn’t see a path of doing so without a major US military intervention that would escalate the conflict. And even if it succeeded, [it] could be a version of catastrophic success, where you create a vacuum that extremists would fill.”

Residents and armed rebels search for survivors among the wreckage of a residential building targeted by a Syrian Air Force strike in the al-Sukri neighborhood of Aleppo, March 25, 2013 (detail) © Moises Saman/Magnum Photos

Seeking continued US support, the Free Syrian Army distanced itself from the Islamic State. “On January first, 2014, the FSA collectively, in northern Syria, declared war on ISIS,” said Charles Lister. “And in ten weeks, ISIS was expelled from four and a half provinces in northern Syria.” The Islamic State concentrated its forces in northeast Syria along the Iraqi border, rampaging across western Iraq, much as Ambassador Ford and others had predicted. The Islamic State’s self-­proclaimed caliphate threatened America’s local allies, the Kurds in Erbil and Baghdad’s Shia-­led government. Obama had ignored the Islamic State in Syria, until it impinged on American interests in Iraq. “I think there was a period of time where again there was a certain amount of panic, particularly involved with the threat to the Yezidis,” Feierstein said. “And I think things in Iraq were unraveling at a pace that was really extremely concerning and that we needed to respond.”

Obama’s attention shifted from Assad to defeating a force dedicated to worldwide terrorism. This led to an overt Title 10 program for the Defense Department to arm anyone who would fight the Islamic State. The beneficiaries were mainly the Kurds of northeastern Syria, who fought tenaciously but had no interest in confronting the Syrian Army. This was not without its complications. Turkey regarded all armed Kurds as terrorists, and many Syrian fighters refused to fight the Islamic State if they could not confront the Assad regime as well. A state of lunacy was reached when the respective insurgent bands of the CIA’s covert and the Defense Department’s overt programs turned their American weapons on each other. Former deputy director of national intelligence Michael Dempsey told me, “Some of the training programs were options between doing nothing and military intervention.” Dempsey, whose brother Martin, as chairman of the JCS, resisted military intervention in Syria, echoed Ben Rhodes: “No one was sure it would work, but we had to do something.”

The triumphs of the Islamic State caused a change in thinking at the White House. One of the Obama insiders I interviewed said, “When I left in 2014, it was game over for dealing with Syria outside of ISIS.” The Islamic State’s sometime rival, occasional ally, and fellow Al Qaeda offshoot Jabhat al-­Nusra also provoked the administration’s ire. Joe Biden spoke to Qatar’s ruler, Sheikh Hamad bin Khalifa Al Thari, in April of 2013, about his support for the extremists. One of Biden’s closest advisers said that the vice president told the emir, “If you gave me a choice between Assad and Nusra, I’ll take Assad.” Biden went public at Harvard’s Kennedy School of Government on October 2, 2014:

Our allies in the region were our largest problem in Syria. The Turks . . . the Saudis, the Emiratis, etc. What were they doing? They were so determined to take down Assad and essentially have a proxy Sunni–­Shia war, what did they do? They poured hundreds of millions of dollars and tens of thousands of tons of weapons into anyone who would fight against Assad. Except that the people who were being supplied were al-­Nusra and Al Qaeda and the extremist elements of jihadis coming from other parts of the world.

US strategists underestimated Russia’s commitment to Assad. Syria was the only one of the twenty-­two members of the Arab League in the Russian camp, dating to its first purchases of Soviet arms in the mid-­1950s. Assad’s survival was a test of Russian credibility. Russia’s air force and army intervened in September 2015, and by December 2016 they helped drive the rebels out of the eastern half of Aleppo. Many regarded that as the war’s turning point, after which Assad could no longer lose.

Syria proved to be Russia’s redemption in the Middle East. Putin became a regional power broker, for the first time selling anti­aircraft systems to Turkey, a NATO member; sending military delegations to Iraq; and organizing discussions about Syria among Turkey, Israel, and several Arab states.

Regime victories followed the triumph in Aleppo, as Russia enabled the Syrian Army, with Hezbollah and Iran, to advance into rebel territory. The insurgents either fought to the death or accepted “reconciliation” that allowed them to go with their families and small arms to their last redoubt in the northern province of Idlib. The negotiators deciding Idlib’s fate included Russia, Turkey, Assad, and most rebel leaders—but not the United States.

The result of US meddling in Syria was failure on all counts. It did not depose Assad, who looks like he is set to hold on to power for years. It did not expel Iran and Russia, whose influence and footprints in Syria expanded. It did not break the Syria–­Hezbollah alliance. Nor did it ameliorate civilian suffering, as refugees either stay in exile squalor or return to demolished homes. It had the unintended consequence of turning Turkey from a traditional ally into a regional adversary. Syrian conspiracy theorists claim the US goal was to destroy Syria, as it did Iraq, to protect Israel. Only if that were true could the United States be said to have achieved any objective.

Children are rushed to a hospital after an alleged chlorine gas attack on Hamouriyah, in eastern Ghouta, March 7, 2018 © Anas Alkharboutli/picture-alliance/Getty Images

The American election of November 2016 appeared to presage disengagement from Syria. Trump canceled Obama’s Title 50 program that armed Syrian oppositionists in July 2017. But one of his senior officials admonished me, “When everyone tells you it’s over, it’s not over. This has a long way to go.” He added, “And it’s still in our interests to try to bring an end to it. But not an end to it just at any cost.” Trump has so far retained the Special Forces troops Obama sent to oppose the Islamic State in northeastern Syria, where they may be vulnerable to Syrian-government-backed insurgents. Turkey has been shelling the US-­backed Kurds in Syria, and Erdogan has vowed to destroy their armed presence along his border.³

Some State Department officials I know refused to discuss the Trump policy, saying the administration was keeping a close eye out for leaks. Anyway, one said, he wasn’t sure what the policy was. Trump’s principal target is Iran, and his advisers propose hitting Iran in Syria while considering support for the Mujahedeen-­e-­Khalq, Iranian militants, and former Saddam Hussein loyalists who featured on the State Department’s Foreign Terrorist Organization List until 2012.

I asked an Obama Mideast adviser what, in retrospect, he would have done differently. “There were serious risks in throwing in our lot with the opposition. We gave them false hope. We didn’t control what they did with their weapons. We didn’t control who they cooperated with. And no matter what, we were still on the hook.” Phil Gordon is one of those who learned something from Syria. Speaking to me in his Council on Foreign Relations office, where he is the Mary and David Boies senior fellow, he reflected,

I’ve obviously thought about this many, many times, because you can’t look back at Syria and conclude anything but, you know, that it’s a horrific tragedy on every level, for the Syrians, for the neighbors, for us. I’ve yet to find the path to a better outcome, other than not fomenting the insurgency in the first place. I think the original sin is getting on board for supporting an armed opposition that had little prospect of actually bringing about a political transition in a more stable Syria.

Does anyone remember the “Vietnam syndrome,” the American aversion to invading other countries following the April 1975 fall of Saigon? It lasted until January 1991, when General Norman Schwarzkopf’s defeat of Saddam Hussein’s occupying army in Kuwait made invasion respectable again. The US armed forces invaded Afghanistan in 2001 and Iraq in 2003. The prolonged warfare in Afghanistan and chaos in occupied Iraq were decisive factors in deterring Obama from invading Syria. Phil Gordon thought the United States Army could have defeated the Syrian Army, but that would have been the beginning, not the end, of the problem: “Once we topple the regime, are the stable moderates going to come to power and govern Syria? I don’t think so. And then you’ve just got a different form of chaos that we’re responsible for.”

Obama’s foreign policy team had advanced degrees from Harvard, Yale, and Georgetown, as well as Rhodes scholarships, and better credentials than most Fortune 500 boards, university faculties, and think tanks. They were “the best and the brightest” of our time, heirs to the wunderkinder John F. Kennedy brought to Washington in 1961.

Kennedy’s “best and brightest” gave the country the mass atrocity that was the Vietnam War, while Obama’s oversaw the devastation of Syria. Like Alec Guinness’s Colonel Nicholson in The Bridge on the River Kwai, Obama’s best and brightest may look with shock at their handiwork and ask, “What have I done?” Colonel Nicholson’s final act, after trying to save the bridge he built for his Japanese captors, was to fall on the detonator and blow it up. Then, he died. In Washington, they go on to think tanks and academe to await the call to serve again.