Barack Obama wanted to get out of the office. The West Wing, airless and tense at the best of times, felt like it was going to war footing. So shortly after six P.M. on the last Friday of August 2013, the president asked his chief of staff and closest aide, Denis McDonough, to join him for one of their periodic end-of-the-day strolls around the South Lawn. In his office just down the hall from the Oval Office, Dan Pfeiffer, Obama’s senior adviser, was heading out to what he figured would be his last dinner date with his girlfriend for a while. He’d already canceled his Labor Day plans on the Outer Banks. Downstairs in his windowless cubbyhole, Ben Rhodes, having cut short a vacation with his wife in Oregon, was fine-tuning a communications rollout for the hectic days to come. Across West Executive Drive, in the Eisenhower building, Philip Gordon, the NSC’s coordinator for the Middle East, was hunkered down, having broken the news to his daughter that he couldn’t take her to the Nationals game and fireworks show to celebrate their shared birthday that night.
As Obama and McDonough circled the South Lawn, their path took them past symbols of the Obama presidency, public and private: the Rose Garden and the Oval Office, but also the swing set the president had installed for his daughters, now rarely used; the White House beehive, yielding honey that darkens in color throughout the summer; the vegetable patch planted by his wife, which supplied the heirloom tomatoes for the First Family’s table. The circuit takes only a few minutes to complete, so the two men did multiple laps, with Obama doing most of the talking.
The president was having second thoughts about the missile strike against Syria he had vowed to carry out if it was determined that Bashar al-Assad had used chemical weapons against his own people. Obama told McDonough he wanted to pull back and seek congressional approval first. He ticked off his reasons: a growing sense of isolation after British prime minister David Cameron, who’d pledged to join the United States in the military operation, had suffered a stinging defeat in Parliament when he put the matter to a vote; a fear that acting without approval might undermine him if he needed congressional backing for the next military crisis in the Middle East, perhaps one involving Iran; and, not least, his own record. At an NSC meeting earlier that afternoon, the White House counsel, Kathy Ruemmler, speaking on a video screen, pointedly reminded him that as a senator, he had called for presidents to seek the buy-in of Congress for military operations.
“I’m well aware of what my position is,” Obama replied curtly.
McDonough was receptive to his boss’s doubts. More so than anyone but Obama himself, he thought that American presidents had reached too reflexively for the military lever over the last decade. From the start of the Arab uprisings, McDonough had resisted the interventionist instincts of his colleagues, whether it was close advisers such as Ben Rhodes and Samantha Power or cabinet members such as Hillary Clinton and David Petraeus. On a trip with lawmakers to the military prison at Guantánamo Bay, Cuba, in June 2013, McDonough told them he thought the conflict in Syria suited America’s purposes just fine because it entangled two longtime American foes, Hezbollah and Iran, in a proxy war. Tom Donilon shared McDonough’s skepticism. “You could read the president’s position through Tom and Denis,” one aide said.
With shadows lengthening across the lawn, Obama and McDonough ambled back up the flagstone path to the Oval Office shortly before seven P.M. Word of the walk had spread rapidly in the West Wing, and when the president’s secretary, Anita Decker Breckenridge, began calling aides to a meeting, they knew something was up. She summoned Pfeiffer; Rhodes; Susan Rice, who had recently replaced Donilon as national security adviser; Tony Blinken; Rob Nabors, the legislative liaison; Brian McKeon, executive secretary of the NSC; and Brian Egan, the NSC’s legal adviser. McDonough, hands jammed in his pockets, stood silently behind one of two beige couches in the office that flanked a marble fireplace with George Washington’s portrait above the mantel. Obama, his tie loosened and shirtsleeves rolled up, sat in one of two leather wing chairs, facing the group. Aides offered various accounts of his opening line.
“I have a pretty big idea I want to test with you guys,” he said, according to one.
“I’ve got a crazy idea I want to talk about,” he said, according to another.
In truth, it was both big and crazy.
Hillary Clinton had been gone for nearly seven months by the time Obama held that fateful Friday night meeting, but there’s little to suggest that her presence would have made any difference. Obama didn’t bother to include her successor, John Kerry, or his defense secretary, Chuck Hagel, in the discussion; the two hours of emotionally charged debate did nothing to dissuade him from shelving his promised missile strike to seek congressional approval. He called the two men at nine P.M., after the meeting had ended, and told them of the change in plans. Hagel was dining with his wife at an Italian restaurant in McLean, Virginia, when Obama reached him; Kerry was at home in Georgetown. (He phoned Hagel afterward to commiserate. “What the hell’s going on?” Kerry asked.) The heavyweight war council of Obama’s first term had given way to an inner circle of advisers who called the shots on critical issues. In this case, where the president essentially presented his decision as a fait accompli, the circle had shrunk to one: Denis McDonough.
There’s equally little doubt that Clinton would have opposed Obama’s decision to forgo the attack. It was a terrible mistake, she told friends and former colleagues. “The Syrians were shaking in their boots at what the Americans were going to do,” a person close to her said. “At a minimum, you would have responded to the chemical weapons, but you also would have created leverage for diplomacy.” Obama had drawn a red line against Assad over his use of chemical weapons—it would be a “game changer,” he warned—and then he had watched Assad trample across that line with an indiscriminate poison-gas attack on civilians. By failing to make good on his threat to retaliate militarily, Obama had eroded the authority of his presidency, weakened the credibility of the United States with allies and enemies, and unwittingly reinforced the perception in the Muslim world that America had no staying power. Clinton had policy differences with the president over Syria during her final months in office, but this was different.
And yet, when Clinton turned up at the White House ten days after Obama’s about-face to take part in a meeting on wildlife trafficking, she was the picture of solidarity. She publicly urged Congress to give the president the authorization he sought for military action. She offered more qualified support for an idea tossed out by John Kerry earlier that day in London and quickly embraced by the Russians: that Syria give up its arsenal of chemical weapons to an outside authority. (Kerry said he had been batting around the idea with the Russian foreign minister, Sergey Lavrov, for a couple of weeks.) “This cannot be another excuse for delay, for obstruction,” Clinton said. Whether through diplomacy or military force, she warned, “the world will have to deal with this threat as swiftly and comprehensively as possible.”
There was nothing accidental about Clinton’s show of support. The day after Obama announced he would go to Congress for approval, McDonough called to brief her about the decision and ask her advice. Clinton, noting the president was headed to a G-8 meeting in St. Petersburg, Russia, later that week, told McDonough it was important for Obama to have credibility when he met Russian president Vladimir Putin, who opposed any action against Assad, a longtime Russian ally. Support for military action in Congress, thin to start with, was withering fast; Obama could not afford to look as if he had no juice. Clinton’s suggestion was small ball—persuade the Senate Foreign Relations Committee, which has authority in matters of war and peace, to hold a vote in favor of military action—but McDonough, who had taken charge of the Sisyphean lobbying campaign, seized it gratefully. He put Obama on the phone with her and arranged for the two to talk again in the Oval Office on September 9, the day of the wildlife meeting.
Rarely had the president so needed his former secretary of state. Isolated at home and viewed as irresolute abroad, Obama was desperate for an ally with domestic and international standing. Clinton felt loyalty to the president; with her own presidential bid still twenty months away, she could afford to line up with him, even in an unpopular cause. But throwing her support behind Obama was not without risk: Opponents of military action were already likening Syria to the Iraq War vote in 2002. “She went out on a real limb in saying she supported the president,” one aide said, ignoring the fact that Obama had vowed to act if Assad crossed the red line he had drawn.
The Syrian civil war was to become the sharpest line separating Clinton and Obama on national security. Her support for funneling weapons to moderate Syrian rebels in the summer of 2012 put her at odds with the president in the last major debate of their years together. At the time, the split seemed a telling, if not theological, disagreement over how deeply to get involved. (Obama eventually did authorize limited covert aid to the rebels.) In hindsight, it looms larger: The inability of the moderate opposition to coalesce as a fighting force opened the door to the Islamic State, which conquered a large chunk of Iraq and established a caliphate in the desert that straddles Iraq and Syria.
Three years later, Syria was more tangled and hopeless than ever.
Russia had entered the war on Assad’s behalf, bombing the remnants of anti-Assad rebels that the United States was trying to help. Iran battled the Islamic State in Iraq while aiding Assad in Syria directly and through its client, Hezbollah. The United States headed a loose coalition, including Turkey and the Gulf states, that was fighting ISIS in Syria and Iraq. What began as a pro-democracy uprising had mutated into a region-wide proxy war involving nearly a dozen countries, whose interests simultaneously overlapped and conflicted. And four years of grinding civil war had produced a grim tide of desperate refugees who were flooding into a panicked Europe.
Against that stygian backdrop, Clinton gave an interview to a Boston television station in October 2015. Asked about the situation, she said, “I personally would be advocating now for a no-fly zone and humanitarian corridors to try to stop the carnage on the ground and from the air.” Again, she split with Obama: He remained opposed to such large-scale American military involvement. Russia’s entry into the conflict was impossible for him to ignore, however. So he opted, characteristically, for a more limited option: deploying a few dozen special operations troops to northern Syria to help the rebels, mostly ethnic Kurds, combat the Islamic State.
Few people, Clinton included, argue that running guns to the rebels back in 2012 would have prevented the rise of ISIS. But Obama, by balking at his own red line and by refusing to arm the moderates when they still had a chance on the battlefield, diminished America’s ability to shape the war or a potential political settlement. Other countries were then able to hijack the conflict by arming more radical insurgent groups, not least the brutal warriors who raised the black flag of the Islamic State. The United States, in Clinton’s oft-used phrase, had not put skin in the game.
“The failure to help build up a credible fighting force of the people who were originators of the protests against Assad—there were Islamists, there were secularists, there was everything in the middle—the failure to do that left a big vacuum, which the jihadists have now filled,” she told the journalist Jeffrey Goldberg in August 2014.
Strong words from someone who, as a rule, soft-pedaled her differences with Obama—in public, at least. Not surprisingly, the president’s aides were angry. Clinton had not, they said, been as passionate an advocate for aiding the rebels in 2012 as she was after the fact, when the Islamic State had become a terrifying media spectacle and a looming political issue in the 2016 campaign. “She never went to the mat on anything that I recall,” one Obama aide told me. Nor was the protracted arming debate as black-and-white as she portrayed it. The president thought the initial proposal—devised by David Petraeus, the CIA director, and seconded by Clinton—was half-cooked and unlikely to alter the course of the war. But he didn’t reject it so much as kick it down the road. Eight months later—after he had been reelected, Clinton and Petraeus were out of the cabinet, and the agency’s new interim director, Michael Morell, had retooled the plan—Obama signed off on a covert program to ship small arms and ammunition, with the help of the Saudis, to Jordan, where it was parceled out to carefully vetted rebel groups.
While Clinton did dramatize her advocacy, the White House narrative diminishes a debate that still ranks as one of the most revealing of the Obama presidency. Clinton and Petraeus were joined by Leon Panetta, the secretary of defense, and General Martin Dempsey, the chairman of the Joint Chiefs of Staff, in supporting the plan. That meant the commander in chief overruled his entire war cabinet, something that had not happened in any other such debate, from Afghanistan to Libya. The fissures flowed downward into the rank and file: The CIA and the State Department did not share their plans for aiding the rebels with the NSC because they knew the White House wouldn’t be receptive. When Obama finally came around, the program he secretly approved in April 2013 was so small and slow to get off the ground that the rebel commanders complained later they never got the guns they needed.
For years afterward, Obama was angry at the way the debate over Syria was framed. He often raised it, unprompted, with reporters. The argument that arming the rebels could have changed the direction of the war, he told Thomas Friedman in August 2014, was ludicrous. “This idea,” he said, “that we could provide some light arms or even more sophisticated arms to what was essentially an opposition made up of former doctors, farmers, pharmacists and so forth, and that they were going to be able to battle not only a well-armed state but also a well-armed state backed by Russia, backed by Iran, a battle-hardened Hezbollah, that was never in the cards.”
In its anguish and ambiguity, the debate over Syria offers perhaps the clearest window into how Clinton and Obama wrestled with America’s role in a fracturing Middle East. Both were appalled to watch Bashar al-Assad, a man they had once hoped would be a reformer, drop barrel bombs and fire poison gas at his people. Both were confounded by the geopolitics of Syria: at once a sectarian civil conflict and a proxy war, involving Russia, Iran, Saudi Arabia, Turkey, and others. Both, but especially Obama, were haunted by Libya, where American intervention had only sowed more chaos and death. Both, but especially Clinton, were mindful of past horrors—Rwanda, the Balkans—where the United States had waited too long or done nothing at all.
“Kosovo, despite the brutality and the horrors of what was happening in the Balkans, was immensely simpler in lots of ways than what we’re talking about with Syria,” Clinton told me in 2013. “There will always be regret when you’re in positions like this when it comes to the horrific slaughter of people trying to express themselves and defend themselves from a government that seems to have lost all sense of responsibility toward their own population.”
Clinton called Syria a “wicked problem,” a phrase used by strategic planning experts to describe “particularly complex challenges that confound standard solutions and approaches.” Obama, in private conversations, referred to it as a “shitty problem,” an equally apt description. Their subtle difference in language laid bare an essential divide between how they viewed Syria: She kept casting about for solutions, however far-fetched. He concluded that there were no solutions—at least none that could be imposed by the United States—and, hence, no case for meaningful military intervention.
“She thought the Syrian crisis is like a raging bull that threatens the China shop,” said Robert Ford, the last American ambassador to Syria. “Success is not guaranteed, but if we don’t try to throw a rope around it, if we don’t try to get a grip on it somehow, we have no chance of steering it at all. My sense of Obama is that he thought, ‘It’s a raging bull, there’s not a lot we can do. Stay the hell away from it.’ ”
For Hillary Clinton, Syria began as an opportunity rather than a threat. On March 2, 2009, during her first visit to Jerusalem as secretary of state, she stood next to the Israeli foreign minister, Tzipi Livni, and announced that the United States would send two emissaries to Damascus. It was the biggest headline of her trip, and with reason. She and Obama were betting that Syria, which had not had a resident American ambassador since George W. Bush recalled the last one in 2005, was the key to unlocking three of the thorniest challenges in the region: a nuclear deal with Iran, a peace accord between Israel and the Palestinians, and a reduction of tensions between Israel and Syria.
Over the next two years, a small circle of American diplomats traveled the road to Damascus, meeting with the stork-like Assad and his corpulent foreign minister, Walid al-Moallem. Also making the pilgrimage was Senator John Kerry. He had cultivated his own relationship with Assad, a fifty-year-old ophthalmologist whose British medical pedigree fooled many into thinking he was a new kind of Arab leader. Some of the issues on the table were unpleasant: reports that Syria was transferring Scud missiles to Hezbollah and Hamas; others less so: a potential peace deal with Israel. Assad was intrigued by the possibility of reclaiming the Golan Heights, the five hundred square miles of rocky highlands seized by Israel in the 1967 war. The White House viewed peace talks as a way to draw Syria out of the orbit of Iran and its terrorist proxy, Hezbollah. Frederic Hof, a seasoned Middle East expert who handled the Syria file for the administration’s special envoy George Mitchell, said that by February 2011, Assad had cleared away most of the obstacles to the Syrian side of a deal with Israel.
“I certainly would not have bet a sizable amount of money that we’d be in the Rose Garden by the end of 2011,” Hof said. “But we were definitely making serious progress.”
Kerry told me that Assad had agreed to the terms of a U.S.-drafted letter, dated May 22, 2010, that sketched out a peace treaty between Syria and Israel. Syria would restore diplomatic relations with Israel and pledge to stop funneling weapons to Hamas, while Israel would return the Golan Heights. Assad hoped this breakthrough would open the door to aircraft parts and other Western technology, as well as help in building an oil pipeline from Syria to Iraq. Kerry took the letter with him to Jerusalem and showed it to Benjamin Netanyahu, who was intrigued but noncommittal.
The portents were good enough for Obama to name Ford as the first U.S. ambassador to Syria in five years. A soft-spoken Arabist with tours in Algeria, Bahrain, and Iraq, Ford was a diplomat out of central casting: genteel but adventurous, Lawrence of Arabia with the voice of a librarian. When he arrived in Damascus in January 2011, his first meeting with Assad was civil. While Assad didn’t give an inch on human rights, he was perfectly charming. “He didn’t want to have a stinky meeting,” Ford recalled.
Even after protests erupted across Syria in March, and Assad’s security forces fired into crowds in the southern city of Daraa, Clinton clung to the idea that Bashar was a reformer, not simply a Western-friendly version of his father, Hafez, author of the Hama massacre, in which tens of thousands of Sunnis had been slaughtered. “There’s a different leader in Syria now,” she told a leery Bob Schieffer on Face the Nation on March 27, 2011. “Many of the members of Congress of both parties who have gone to Syria in recent months have said they believe he’s a reformer.”
By summer, with crowds chanting in the heart of Damascus and the Syrian army turning its guns on them, nobody had illusions about Assad any longer. On July 8, Ford paid a risky visit to Hama, site of the 1982 massacre, where five hundred thousand people had gathered to protest against the regime. As the ambassador’s gray SUV inched through the crowd, it was strewn with roses and olive branches. Assad was livid, accusing Ford of inciting antigovernment rage. But the State Department, which had run out of patience with the Syrian leader, was pleased. So was the White House, for which the incident was proof that sending a diplomat did not mean caving in to the regime.
“Well done,” Bill Burns, the State Department’s top career diplomat, told Ford in a phone call.
Emboldened by her envoy, Clinton declared three days later that the Syrian leader had lost legitimacy. “We have absolutely nothing invested in him remaining in power,” she said to reporters. A month later, Obama went further. “For the sake of the Syrian people,” he said in a written statement, “the time has come for President Assad to step aside.” Obama saw no need to back up his demand with the threat of military action. A stream of American intelligence reports was predicting that the regime’s days were numbered, although analysts differed on the numbers.
Not everybody in the White House was convinced. Steven Simon, an NSC senior director who worked on the Middle East, cowrote a memo with Dennis Ross on the likely trajectory of the Arab uprisings. Nursing doubts that Assad was about to fall, Simon added a section warning that the White House’s hands-off strategy in Syria might not work. It was stripped out before the report went to the president. Sure enough, Assad was still in power at the beginning of 2012. Bolstered by Hezbollah and Iran, he carried out a systematic campaign of torture and killing of demonstrators. At that point, John McCain and other lawmakers called for the United States to intervene.
Obama, however, was deeply reluctant, and any thoughts of military action to protect civilians were dispelled by a slide show in the Situation Room early in 2012, given by Marty Dempsey. A low-key, publicity-shy Irishman who had replaced the more extroverted Mike Mullen as chairman of the Joint Chiefs the previous October, Dempsey would become one of Obama’s most trusted generals. It was easy to see why: He was an articulate, effective advocate for avoiding rash military action in Syria—the same role Mullen had tried to play on Libya. In a set of slides showing Assad’s air defenses, Dempsey warned that it would take as many as seventy thousand American servicemen to dismantle the antiaircraft system and enforce a no-fly zone over the country.
With American military action off the table, Clinton returned to a familiar slog of urgent diplomatic meetings in European capitals about Arab wars. Only Syria wasn’t going to unspool like Libya: Russia had a naval base in the country and viewed Bashar al-Assad as a strategic ally; still seething at how NATO’s humanitarian intervention in Libya had turned into a campaign of regime change, it had no plans to sanction a pressure campaign against Assad at the United Nations. The Russians vetoed even a watered-down Security Council resolution condemning the regime’s violence. As the Syrian uprising metamorphosed into a full-fledged civil war with a shifting cast of rebel groups, Clinton was pressed by the Saudis, Turks, Qataris, and Emiratis to supply arms to the opposition. Robert Ford, now effectively the ambassador to the rebels, was hearing the same plea for weapons from leaders on the ground.
In February 2012, the State Department shut down the American embassy in Damascus, evacuating Ford and his staff. It cited the escalating violence in the capital but did not mention the source of that violence: Jabhat al-Nusra, a well-financed, frighteningly successful militant group linked to al-Qaeda (doing so would have undercut the White House narrative that it had degraded al-Qaeda). To Ford, the inroads made by al-Nusra drove home the need for the United States to get weapons into the hands of more moderate rebels, chiefly the Free Syrian Army. Soon after he got back to Washington, he paid a call on Dave Petraeus at the CIA. The two were old friends from Iraq: Ford had run the political office at the Baghdad embassy while the general was making plans to reach out to Sunni tribal leaders in Anbar Province.
“You guys have got to get into the game in Syria,” Ford told Petraeus. “We’ve got to be helping the opposition because it’s going to get really ugly.”
“Let me get back to you,” Petraeus said.
Until then, the White House had justified its refusal by saying it did not want to further “militarize” the conflict. Obama and Clinton both worried that the United States did not know the rebels well enough to tell the good guys from the bad guys. They feared that weapons would fall into the wrong hands. Their nightmare scenario was a Syrian jihadi armed with an American antiaircraft gun taking out an El Al passenger jet.
The United States had been delivering nonlethal assistance to the Syrian opposition since the summer of 2011. At the University of Aleppo, which had become a hotbed of anti-Assad activity, the State Department was taking small groups of students to Turkey for training in the techniques of nonviolent resistance. In a heartbreaking turn, Syrian security forces stormed the campus in May 2012, killing at least four activists; one was hurled to his death from a fifth-floor window. It was a chilling demonstration of what Tom Friedman once called the “Hama Rules,” the scorched-earth tactics that Assad’s father used so effectively to crush dissent. That Assad’s troops would hunt down and kill young activists this way suggested a regime with no shame. For many in the State Department, it sealed the argument that American aid should no longer simply be nonlethal or humanitarian.
Over the next few months, staffers at State and the CIA quietly worked together to develop an arming proposal. For an administration that prided itself on tight coordination—a “robust inter-agency process,” to use Tom Donilon’s preferred term—there was remarkably little discussion about these plans between the two agencies and the NSC. The diplomats knew their ideas were not likely to get a warm reception from the president, so they were not very forthcoming with their White House counterparts. Some in the White House viewed the State Department as clueless, fixated with planning for a post-Assad Syria when it was far from clear that Assad was going anywhere.
While the planning occurred well below Clinton’s level, she was undergoing her own change of heart on the arming concept. As with Libya, she kept hearing from leaders in the Persian Gulf that if the United States did not start backing the opposition, it would have no ability to control events. On a Saturday afternoon in July 2012, Clinton invited Petraeus to lunch at her home in Washington. There were several items on the agenda; Ford and his colleagues made sure one of them was arming the rebels. “He had already given careful thought to the idea,” Clinton wrote in her memoir, “and had even started sketching out the specifics and was preparing to present a plan.”
In fact, Petraeus was way ahead of Clinton. A few months earlier, he had met quietly in Istanbul with the heads of twelve intelligence services from America’s allies and countries in the region. The subject was Syria, and the goal was to better coordinate efforts to aid the rebels. Afterward, the CIA began secretly advising on a military airlift operation in which Saudi, Qatari, and Jordanian cargo planes would transport arms and equipment for various opposition groups to airports in Turkey or Jordan. Though the United States was not supplying weapons itself, the agency’s advisory role allowed it to keep tabs on where the arms were flowing—and to steer them away from malefactors.
At other meetings in Jordan and Saudi Arabia, Petraeus kept getting pressure from Arab officials to begin funneling weapons directly to the rebels. In July 2012, he met with King Abdullah of Saudi Arabia, who bore a deep hatred of Assad. The next day, the king named Prince Bandar bin Sultan, the flashy, cigar-smoking former ambassador to Washington, as the head of the Saudi intelligence service. Bandar’s desire to oust Assad was well known; putting him in that job was an unmistakable sign that the House of Saud would aggressively lobby the United States for help in doing that. The CIA director’s enthusiasm for arming the rebels was heavily stoked by Prince Bandar, according to a senior American official. (Saudi Arabia would later end up bankrolling much of the CIA program, under a secret arrangement code-named Timber Sycamore.) Petraeus declined to discuss his role in the debate over arming or training the rebels.
Meanwhile in Syria, the war took an ominous turn. Intelligence agencies began intercepting communications that suggested Syria was moving and mixing chemical weapons agents, a prelude to a possible attack. On August 20, 2012, taking the podium in the White House briefing room, Obama made one of the most fateful statements of his presidency. “We cannot have a situation in which chemical or biological weapons are falling into the hands of the wrong people,” he said. “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 weapons moving around or being utilized.
“That would change my calculus,” the president added. “That would change my equation.”
For Obama to draw a red line against chemical weapons, even if he did not act against Assad’s barrel bombing of Aleppo, was less surprising than it might have appeared. The use of these weapons violated the Geneva Protocol and the Chemical Weapons Convention. That was something that Obama the lawyer and custodian of international norms could not abide. But the president, his aides conceded later, should have been more careful about using the phrase “red line.” He had boxed himself in.
It was at this moment that Petraeus, backed by Clinton, made his pitch for arming the rebels. People who were in the Situation Room that September day recalled the CIA director dominating the proceedings. He leaned so far forward across the table, his head cocked toward the president, that he blocked Obama’s view of everybody sitting on the far side of him. His presentation was vigorous, detailed, and self-confident, reflecting the experience of a commander who had championed covert paramilitary operations in Iraq. Some found it over-the-top, given that the director of the CIA is supposed to offer the president dispassionate assessments of the intelligence, not be a policy advocate. Petraeus used “hot rhetoric,” one person recalled, emphasizing the need to move “now versus later.”
Obama listened quietly, leaning to one side in his leather chair in what one aide described as his “senior executive mode.” He asked a few questions but did not challenge Petraeus. Afterward, he went around the table and polled the team. Clinton said she favored the plan as a way to force Assad into negotiations. To some in the room, her emotion didn’t match the case she was making. “You had the libretto and then you had the notes,” one said. Panetta threw in his support, as did Dempsey, even less fervently than Clinton. Panetta summed up the case in his memoir, Worthy Fights. “All of us believed that withholding weapons was impeding our ability to develop sway with those groups and subjecting them to withering fire from the regime,” he wrote. The president, he added, was “initially hesitant.”
So was most of the White House. Biden thought arming the rebels was a “stupid idea,” said a person in the room. (He had also advised Obama against laying down a red line.) Donilon and McDonough were both skeptical, though Donilon’s position evolved over the coming months while McDonough’s did not. Susan Rice spoke out most forcefully against it. Appearing on a video screen from the United Nations, she argued it would draw the United States into a quagmire and muck up Obama’s second-term agenda. It was a remarkable turnabout for someone who had led the charge on using force in Libya, and had cultivated a reputation as an advocate of humanitarian interventions generally. This time, she was in lockstep with the boss.
“We asked a lot of questions,” a senior White House official recalled. “ ‘What would be the assessment of the impact this would have? What would be the chain of custody the weapons would have? Who trains the people to use the weapons? Is there a command-and-control structure around these people? Or are we just dumping the weapons in?’ There weren’t a lot of clear answers to those questions.”
For the pro-arming camp, the case came down to a process of elimination. “ ‘We tried a range of options and nothing has worked. So why not try this?’ ” said Steven Simon, who watched from a chair along the wall. “You could sense what the president was thinking: ‘For something with such a vague, speculative outcome, I’m going to get the United States involved in a civil war in Syria?’ ” Clinton and Panetta both fell back on the need to get “skin in the game.” It didn’t help that neither meant it in the Wall Street context in which the phrase is commonly understood—investors putting their own money into a deal to limit the risk they are willing to take. In Clinton’s use of the term, having skin in the game would increase, not limit, the risk.
Then there were the inconvenient facts of history. The CIA, at the behest of Michael Morell, had taken a hard look at its record of running guns to insurgent fighters—a murky trail that ran from the Bay of Pigs in Cuba to the contras in Nicaragua. “Needless to say, it was just a concatenation of miserable failures, of backfiring policies, and all kinds of mayhem,” Simon said. There was one notable exception: Afghanistan in the 1980s, where the agency funneled weapons to the mujahedeen fighting their Soviet occupiers, but that only worked because the agency had Pakistani intelligence officers on the ground in Afghanistan, helping the mujahedeen. (And even then, many of those fighters ended up, years later, with the Taliban or al-Qaeda.) There was no equivalent in Syria.
Finally, there was an election in two months. If Obama was reluctant on the merits to get drawn into Syria, he was certainly not going to do it just before he faced the voters. He thanked Petraeus for his presentation and ended the meeting without a decision. “In Arab culture,” Robert Ford observed, “they have a saying: ‘No answer is the answer.’ ”
Days after that meeting, Islamic militants attacked the U.S. compound in Benghazi and killed four Americans, confronting Obama and Clinton with an election-year crisis that overshadowed Syria. Petraeus, meanwhile, had become embroiled in a personal crisis over an affair with his biographer, which would precipitate his resignation the day after the election. In early December, an ill, dehydrated Clinton slipped and fell in the bathroom of her house, suffering a concussion and blood clot. She was sidelined for a month. Arming the rebels had lost its moment and its main advocates.
Yet in December, Obama convened another NSC meeting, without Petraeus or Clinton, to debate the issue once again. The CIA’s chair was now occupied by Morell, a career intelligence analyst who had briefed George W. Bush on the day of the 9/11 attacks and became the acting director after Petraeus left. Low-key, with none of his predecessor’s star power, Morell nonetheless brought strong opinions and a fierce loyalty to his institution. He had retooled the Petraeus plan to address Obama’s skepticism, sharpening U.S. control over the weapons. He dialed back claims that it would be a panacea for the rebels and conceded the risks, particularly those of a Sunni slaughter of Syria’s Alawite minority. “If a group of armed rebels went back to an Alawite village and killed a bunch of women and children,” he warned, according to a person in the room, “the U.S. would have blood on its hands.”
The same questions swirled: How would this alter the war? What were the risks? Obama thanked everybody again and said he wanted to think about it, but his body language gave him away. He still wasn’t satisfied with the level of vetting for the rebels or with assurances that this would not be a slippery slope for the United States, one that led to direct American military involvement. “They could have tweaked this thing until kingdom come,” said a former White House official. “It wouldn’t have made any difference. He just didn’t think it was a good idea, period.”
By early 2013, however, things had changed dramatically on the battlefield in Syria. Assad was no longer on his heels; intelligence reports said he had regained the offensive. His patron, Iran, had come to his rescue, replenishing his munitions depots. The Free Syrian Army was in disarray, running low on guns, while militant groups, chiefly the Qaeda-linked Jabhat al-Nusra, were in the ascendancy, drawing recruits from more moderate groups who sometimes brought foreign-supplied weapons with them.
Until then, Obama had viewed Syria only from the distant vantage point of the Situation Room, in the basement of the West Wing. But in March 2013, he went on a three-day trip to the Middle East that included his first stop as president in Israel. His travels exposed him to the fears of Syria’s neighbors. The Israelis were ambivalent about Assad; they disliked him but feared that what followed his regime could be worse. In a meeting in Jerusalem, Benjamin Netanyahu warned Obama that Assad’s chemical weapons could fall into the hands of Hezbollah. Speaking afterward to reporters in the courtyard of the prime minister’s residence, the president reiterated his warning that the “use of chemical weapons is a game changer.”
The next day, in Jordan, Obama got an earful. King Abdullah II, who also despised Assad, hosted the president at a late-night dinner in his palace in Amman, along with Tom Donilon and John Kerry, who had replaced Clinton two months earlier. Jordan, the king told his guests, was buckling under more than one hundred thousand Syrian refugees. He urged Obama to do more to end the war. Jordan was already the site of a secret camp where the CIA was training small cadres of moderate rebels. It had offered the United States bases to carry out drone strikes in Syria, which the White House refused.
All these issues were on the president’s mind the next morning as he took a solitary walk through the rose-hued canyons of the ancient city of Petra.
Back in Washington, the CIA kept tinkering with its proposal to arm and train the rebels. In April 2013, the NSC staff sent the president a decision memo, a document that laid out the arguments for a covert program, giving Obama another chance to review his thinking. The basic rationale for aiding the opposition had changed little from the previous year, though the memo punched up the need for the United States to have a seat at the table in deciding Syria’s future—something it would get by being more involved in the war. This time, to the surprise of NSC staffers, Obama sent it back with the box checked, “Approved.” Normally, there would have been an NSC or deputies meeting to debate such a change in policy. In fact, Obama’s check mark was slightly below the “Approved” box, leading some staffers to muse, half in jest, that maybe he had meant to check “Disapproved.” The CIA called the White House to make sure the decision had come directly from him.
Obama’s shift coincided with new intelligence reports: The Syrian regime had used the chemical agent sarin in small-scale attacks the previous month, in a village near Aleppo and on the outskirts of Damascus. Outside agencies had tested soil samples from the site and blood taken from the victims; there was little doubt that Assad had crossed Obama’s red line. Inside the White House, nobody was explicitly linking the WMD attack with the decision to arm the rebels. And regardless of the reports, nothing more happened for three months after Obama approved the CIA’s covert program: No weapons flowed, no public announcement was made, no funding was requested from Congress. The program was not only clandestine, it was invisible.
Certainly, Obama’s reticence about being drawn into a civil war was at the root of his halfhearted approach to Syria. But in a White House where many of the top officials, including the president, had law degrees, the lawyers played an important, underappreciated role. They curbed efforts to bolster nonlethal aid for the Syrian opposition (covert aid came under less scrutiny). The legal argument was this: Even though Obama had called on Assad to step down, the United States was not at war with Syria. Providing night-vision goggles, communications gear, or even food rations to those trying to oust him therefore could be a violation of international law. Weren’t Assad’s barrel-bomb attacks on civilians also a violation of international law? the diplomats replied incredulously. At one State Department meeting about a scheme to transport aid across the Syrian border, a department lawyer warned, “You guys all think you’re James Bond, but I’m telling you, if we do this, we’re going to go to jail.”
By now, the ragtag state of the Free Syrian Army was less of a problem than the threat from Assad’s chemical weapons, and the debate in the White House shifted from aiding the rebels to direct military action. Over four decades, the CIA estimated, Syria had accumulated large supplies of sarin, mustard gas, and cyanide, which it could deliver by aerial bombs, ballistic missiles, and artillery rockets. These were stored in depots scattered throughout the country, some close to populated areas. The Pentagon prepared a menu of options for Obama that included commando raids to secure the stockpiles and strikes on Syrian planes from American ships in the Mediterranean. Securing all the known weapons sites, Panetta wrote in his memoir, would have necessitated 75,000 to 90,000 troops, as many as were in Afghanistan. “I considered that impossible,” he said, “and my colleagues agreed.”
As spring turned to summer, however, the war drums were beating again—and again, Bill Clinton was adding to the din. On June 12, 2013, he sat on a flag-draped stage in Manhattan with John McCain, who had been castigating Obama for months for his lack of action. During the Q&A session at the gathering, sponsored by the McCain Institute for International Leadership, the subject of Syria came up. “Some people say, ‘OK, see what a big mess it is? Stay out!’ I think that’s a big mistake. I agree with you about this,” Clinton told McCain. “Sometimes it’s just best to get caught trying,” he added, using a well-worn Clinton line that was nevertheless widely reported.
The same day, Obama’s war council held another meeting in the Situation Room. The intelligence assessments were now definitive: Assad had used sarin gas on his people. Estimates put the number killed at between 100 and 150. John Kerry, who lobbied more aggressively than Hillary Clinton for increased aid to the rebels, brandished a State Department document that warned if the United States did not impose consequences on Syria for these attacks, Assad would view it as a “green light for continued CW use.” Obama remained opposed to military action, but the White House knew it had to do something to look responsive. On June 13, it scheduled a press call with Ben Rhodes that may qualify as the most oblique declaration of war since Lyndon Johnson asked Congress to pass the Tonkin Gulf Resolution. Confirming the decision that Obama had made two months earlier, Rhodes said the United States would provide “assistance that has direct military purposes” to the Supreme Military Council, the armed wing of Syria’s opposition. Reporters peppered him with questions: What kind of assistance? He wouldn’t say. Who would provide it? He wouldn’t say. How would it be provided? Again, he wouldn’t say.
The president said nothing at all.
The truth is, the plan was a baby step—or, as a former State Department official less delicately put it, a case of him “salami-slicing the baby.” When the CIA’s weapons finally began flowing several months later, it was a trickle. A rebel leader told Robert Ford that at the end of 2014, his men were receiving about 36,000 bullets a month from the United States. In combat, a soldier fires between 100 and 200 bullets a day. That meant the CIA was arming between six and twelve fighters. “It’s sort of stupid,” the rebel leader told him. The ambassador agreed: A few months earlier, Ford had resigned from the Foreign Service in protest. “I found it ever harder to justify our policy,” he wrote in a New York Times op-ed. To alter the state of the war and force Assad into a negotiation, the Free Syrian Army needed heavier weapons: mortars, rockets, even surface-to-air missiles.
“Dribbling in little bits of aid wasn’t helping them or helping efforts to find a political solution through negotiation,” Ford told me.
Obama’s halfhearted approach was causing strains at higher levels, too. Chuck Hagel, the Republican former senator from Nebraska whom Obama had asked to replace Leon Panetta as defense secretary in 2013, became frustrated the following year because he could not extract a pledge from the White House to defend the rebels it had trained and armed if they came under attack by Assad’s forces. In an angry two-page memo to John Kerry and Susan Rice that October, Hagel complained about this lack of American commitment and the absence of a broader political strategy toward Syria, which he said was hampering efforts to line up support from allies such as France and Turkey for the military campaign against the Islamic State. Hagel copied Denis McDonough, and asked him to hand the memo to the president.
“I could never get anything out of the White House,” Hagel said in an interview after he left the administration. “They had these never-ending meetings, which would never get to the real issues. They never looked down the road or anticipated anything.”
A war hero in Vietnam who made a fortune in cellphones, won election to the Senate, and then defied his party’s president on the Iraq War, Hagel was not used to failure. He thought he had a personal bond with Obama, having befriended him in the Senate and traveled with him to Iraq and Afghanistan during the 2008 campaign. But Syria would drive a wedge between them: White House officials told reporters he was a cipher during policy debates; he concluded the president was captive, as he put it, “to a very incompetent, inexperienced White House staff.” A month after Hagel wrote the memo complaining about the Syria policy, he resigned under pressure—the fall guy, he believed, for a national security team in disarray.
Across the administration, there was a disquieting sense that Syria could end up as Obama’s Rwanda. Samantha Power, speaking at the Holocaust Memorial Museum in Washington, defended her boss’s record in fighting atrocities in Libya and central Africa. “But against all of this,” she said, “there is Syria.” Tom Malinowski, at his swearing-in ceremony as the assistant secretary for democracy and human rights, noted it was the twentieth anniversary of the Rwandan genocide. “What will our kids and grandkids ask us about our time here twenty years from now?” he asked. The reference to Syria was clear, if unspoken.
Just after two A.M. on August 21, 2013, the Syrian army fired rockets tipped with sarin gas into rebel-controlled suburbs of Damascus. By dawn, the hospitals were overflowing with victims, their mouths foaming and bodies convulsing. The dead piled up by the hundreds, covered in ice to prevent their corpses from rotting in the heat. This was not an isolated attack, with a few dozen victims. It was an atrocity, the worst chemical weapons assault since the Iran-Iraq War, and it was precisely what Obama had in mind when he drew his red line the previous summer. Speaking to half a dozen aides in the Oval Office the next morning, the president ordered them to present him with military options at an NSC meeting that afternoon.
“I set out a red line,” he said. “It looks like he crossed it. If that’s the case, we need to respond forcefully.”
The aides nodded in agreement—except for McDonough, whose furrowed brow gave him away.
“You don’t agree, Denis?” Obama asked.
“I don’t,” he replied.
“I figured you would say that, but why?”
“Our position all along has been not to get involved,” McDonough said. “We shouldn’t get involved.”
“Denis,” Obama said, “Assad just carried out a chemical weapons attack. I was pretty clear about what that would mean.”
At the NSC meeting that afternoon, and every meeting over the coming week, the discussion was about selecting targets for Tomahawk missile strikes. The Pentagon’s plan was to hit four of Assad’s main command-and-control centers; the missiles would be fired at three A.M. to keep casualties as low as possible. Which is why Obama’s aides were so stunned on the evening of August 30 in the Oval Office, when the president, after his walk with McDonough, told them he was holding off on a strike until he got congressional approval. The pushback from the staff was intense: Dan Pfeiffer told him there was only a fifty-fifty chance he would win a vote in Congress on military action, a prediction that proved wrong by 100 percent. Susan Rice told him it was important, as a matter of executive privilege, that he not back down. A picture taken by White House photographer Pete Souza captured the anguish in the room: Pfeiffer leaning forward on the sofa, chewing on a fingernail; Rhodes slumped back, resting his head on his hand, a legal pad on his lap.
Lawyerly as always, Obama laid out his case. His backing of the NATO air campaign in Libya had left a sour taste among many in Congress. Moving swiftly there had been vital to avert a slaughter in Benghazi, but that wasn’t the case here. General Dempsey had told his commander in chief that the two or three days of strikes he was planning would be just as effective “in three weeks as in three days.” David Cameron’s defeat on the war vote in Parliament had given him pause. Yes, the president granted, Cameron had handled the vote clumsily. But it accurately reflected public sentiment in Britain. “We similarly have a war-weary public,” Obama pointed out. Ordering another military action over the heads of Congress, he told his aides, would contradict the spirit of his speech the previous spring, in which he tried to move America off the perpetual war footing of the post-9/11 era.
To many, even former cabinet members, Obama was simply looking for an excuse to avoid pulling the trigger. Throwing himself at the mercy of a risk-averse Congress, Panetta wrote, was “an almost certain way to scotch any action,” as the president “well knew.”
“You cannot say things like ‘a red line’ or ‘Assad must go’ as a throwaway line,” Hagel told me. “The president of the United States can’t do that.” Clinton was more diplomatic, though her neutral, just-the-facts description of the episode in her book suggests someone who had no intention of sharing her true feelings. A more accurate gauge of Clinton’s position on Syria came at the one hundredth anniversary gala of The New Republic in November 2014, when the magazine’s former literary editor, Leon Wieseltier, barged into a cocktail conversation Bill Clinton was having with two of Wieseltier’s colleagues about macroeconomic policy.
“Excuse me, Mr. President,” he asked. “If you were still in office, you would have intervened in Syria, right?”
“Yes,” he replied. “That’s the family policy.”
Hillary’s lobbying on Capitol Hill helped Obama eke out a minor victory in a 10–7 vote in favor of military action on the Senate Foreign Relations Committee. But facing a solid wall of opposition in the broader Congress, the president grabbed a diplomatic lifeline: a proposal the Russians made, seizing on John Kerry’s comment, to have Assad surrender his chemical weapons to an outside authority. Months later, Obama and his lieutenants would point to the success of that agreement as vindication of his decision not to strike. “If the president had bombed for ten hours or two days,” Kerry told me, “he would not have gotten all the weapons out of Syria.”
Yet the red line wouldn’t fade. “I’ve heard it a hundred times if I’ve heard it a dozen times,” Kerry said of his exchanges with foreign ministers. “ ‘Gee, the president announces a red line and then he didn’t bomb.’ It has entered into the ether of diplomatic mythology.”
Fairly or not, the symbolism of Obama drawing a line and failing to enforce it far outweighed the tangible dividends of the chemical weapons deal. It dismayed his friends, disgusted his critics, rattled the nation’s allies, and perhaps emboldened its adversaries. “There was a fear,” said Wolfgang Ischinger, a prominent German diplomat who served as ambassador to the United States, “that if the U.S. doesn’t act, then who else will?” Some point to that weekend, when the guns of August did not sound, as an irreparable blow to America’s credibility.
George Mitchell, the Senate elder and frustrated peacemaker of Obama’s first term, has watched presidents since Reagan struggle to square agonizing real-world decisions with the enormous symbolic power of their office. “The American people,” he said, “are very fortunate that we don’t have a president who will push the military button the first chance we have.”
Still, Mitchell said, “Making the statement about the red line in Syria, then not following through on it, clearly has had an adverse effect. You cannot view each decision in isolation. Everything a president says or does affects everything else he does. It’s important to keep in mind the assembling of power and influence, both internally and externally, and to gauge actions in that context. The president hasn’t focused as much on that as on the detail and nuance of each of the issues that he’s faced. It may sound harsh, but that’s the reality of being a leader.”