The Long Game

How Obama Defied Washington and Redefined America’s Role in the World


By Derek Chollet

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In this inside assessment of Barack Obama’s foreign policy legacy, Derek Chollet tackles the prevailing consensus to argue that Obama has profoundly altered the course of American foreign policy for the better and positioned the United States to lead in the future.

The Long Game combines a deep sense of history with new details and compelling insights into how the Obama Administration approached the most difficult global challenges. With the unique perspective of having served at the three national security power centers during the Obama years — the White House, State Department, and Pentagon — Chollet takes readers behind the scenes of the intense struggles over the most consequential issues: the wars in Iraq and Afghanistan, the meltdown of Syria and rise of ISIS, the Ukraine crisis and a belligerent Russia, the conflict in Libya, the tangle with Iran, the turbulent relationship with Israel, and the rise of new powers like China.

An unflinching, fast-paced account of U.S. foreign policy, The Long Game reveals how Obama has defied the Washington establishment to redefine America’s role in the world, offering important lessons for the next president.




On the last Saturday of August 2013, Labor Day weekend, the United States was once again about to go to war in the Middle East.

Less than two weeks earlier, in the middle of the night on August 21, the Syrian military had attacked rebel-controlled areas of the Damascus suburbs with chemical weapons, killing nearly 1,500 civilians, including over 400 children. Horrific video footage showing people with twisted bodies sprawled on hospital floors, some twitching and foaming at the mouth after being exposed to sarin gas, had ricocheted around the world. This atrocity opened an ugly new chapter in a brutal Syrian civil war that had already cost over 100,000 lives, and America needed to respond.

The day after the attacks, President Obama’s national security advisor, Susan Rice, called an emergency meeting at the White House to discuss what to do. Because it was the end of summer, many cabinet officials were out of Washington, so they participated by secure video while those of us in town assumed our customary seats around the Situation Room table.

We first tried to establish exactly what had happened and who had done it. There was considerable discussion of the intelligence we had collected. We knew chemical weapons had been used, but we wanted to be sure we could conclusively establish the Assad regime’s culpability. The evidence turned out to be overwhelming: it included eyewitness accounts from medical personnel and information about Syrian military officials giving specific instructions to mix the chemicals and use them. This brazen assault had clearly crossed the “red line” that President Obama had enunciated a year earlier.1

The discussion quickly turned to whether and how the US should respond militarily. There were a variety of targets that could be hit, from the chemical sites themselves to military headquarters, runways, and even Assad’s palace or presidential helicopter fleet. But there were many concerns about the danger to American pilots (Syria had one of the most sophisticated air defense networks in the world), as well as the possibility of escalation.

Everyone understood the risks. There was no question the US had the capability to act decisively, but there was deep uncertainty about where military intervention would lead. The mood in the room was tense but resigned. A decade after the invasion of Iraq, there was a sense that America was about to go over another Middle Eastern waterfall.

As Rice went around the room (or asked those on the screen) for a recommendation, nearly everyone advocated for quick action. The most notable voice of caution came from Denis McDonough, the president’s influential and highly effective chief of staff. McDonough questioned the effectiveness of airstrikes and warned of the risks of getting bogged down in yet another Middle East quagmire. A forceful advocate, he seemed to be putting extra emphasis on this point to ensure that he preserved for the president what he called “decision space.” I sensed he felt the need to play a role similar to that of George Ball, the great diplomat who, in that same room decades earlier, had intentionally assumed the part of “house dove” during Lyndon Johnson’s fateful deliberations about the Vietnam War.

The meeting concluded with a unanimous decision to prepare for military strikes. To do this right, it would take some time to prepare. Tasks were handed out to scrub the intelligence further with an eye to what could be released publicly, construct the legal basis for action, build a campaign for diplomatic support, intensify outreach to the Congress and, most important, begin to make the case to the American public.

Military planners at the Pentagon started working around the clock to prepare for a series of air strikes, with the specific aims of deterring Syrian leader Bashar al-Assad from launching more chemical attacks and degrading his military’s ability to do so. As the assistant secretary of defense whose portfolio included Europe and the Middle East, I had two roles: in addition to working with the secretary of defense, Chuck Hagel, and other senior defense officials on various aspects of planning the strikes, I stayed in daily contact with my counterparts from the two countries most likely to contribute to them, the United Kingdom and France, to coordinate our positions and ensure nothing was overlooked. We also were in close contact with the Israelis, who, while not involved in the military planning or potential operations, were keenly focused on Assad’s chemical weapons and knew something about conducting airstrikes in Syria, having destroyed a North Korean-supplied nuclear reactor in the Syrian desert in September 2007.

BY LABOR DAY weekend, all the pieces were in place. The Pentagon planners had narrowed the target list to around fifty sites, with the initial wave of strikes involving Tomahawk cruise missiles fired from five Arleigh Burke-class destroyers positioned in the Mediterranean Sea. The ships were in position—in Pentagonese, they were “in the basket”—poised to launch strikes within minutes of the president giving the order. The French were ready to go as well. The British, however, had bowed out after the UK House of Commons had refused to support the Prime Minister’s request that the country join the US.2

Secretary of State John Kerry laid out the public case for intervention. In a speech encouraged (and partly crafted) by the White House and delivered in the State Department’s ornate Treaty Room on Friday, August 30, he outlined what we knew about the chemical attack and Assad’s role in it. Citing the “indiscriminate, inconceivable horror of chemical weapons,” Kerry made a forceful call for action, arguing that the whole world would be watching what the US did or did not do.

For Kerry, this moment was rich with irony. In 2004, his campaign for the presidency had been defined by, and ultimately faltered over, his position on the Iraq War. A key event in the lead-up to that conflict had been when then-Secretary of State Colin Powell went to the UN Security Council to make the case for war, citing specific evidence of Saddam Hussein’s possession of weapons of mass destruction. Now Kerry was speaking to the world from the State Department about another threat posed by such weapons, detailing intelligence and delivering a stark warning about the costs of inaction. While he was careful to note that no decision had been made, the speech was an unmistakable signal that intervention was coming.

HEADING INTO THE weekend, the Pentagon had made plans for round-the-clock staffing coverage over the holiday, when we thought the operation would start. And on Friday night, we received word that the president wanted to see his top advisors at the White House at 10 a.m. on Saturday. We assumed this would be the final signals check before the Tomahawks flew.

Early Saturday morning, as I was walking with my wife and young son to grab a quick breakfast before heading into the Pentagon for what I expected to be a long and dramatic weekend, my Blackberry buzzed with a call from “Cables,” the office of the secretary of defense’s switchboard. It was Mark Lippert, an old friend who was then Hagel’s chief of staff, with surprising news: the president had called Hagel late the night before and told him he “wanted to explore another option.” Instead of ordering strikes immediately, the president wanted to pump the brakes and first go to Congress to ask for its authorization.

I was shocked. I had been in most of the White House meetings up to that point, and while the issue of legal authorities and Congress had come up, it was clear the president had all the domestic legal authority and international justification he needed to act. The question of asking for a congressional vote had never been discussed at length; some had suggested we should ask for a vote, but there was skepticism it would pass, and therefore a feeling the question should not be asked. For an administration that prized careful and inclusive deliberation, it was unusual that a decision this big would arise so suddenly without first being thoroughly pored over in the interagency process.

Once the surprise wore off, I found myself thinking that, while abrupt, unexpected, and unorthodox, this was the right move. Not because of any legal reason or question of constitutional powers, but because Congress and the American people needed to be fully invested in what we were about to do and prepared to accept the consequences.

It turned out that the president had decided to do this on his own the night before. After a now-famous walk around the White House South Lawn early Friday evening with McDonough, he told his advisors huddled in the Oval Office that he had decided to take the question to Congress. Subsequent accounts of the meeting described his closest aides being as surprised as the rest of us, with some arguing that it was a bad move.

There were many reasons for the president’s hesitation. As he later explained to the journalist Jeffrey Goldberg, he worried Assad would use the UN inspectors on the ground as human shields (as had happened in Bosnia and Iraq in the 1990s) and that the strikes would merely dent Syria’s massive chemical weapons arsenal, creating an even more dangerous situation. Most fundamentally, Obama believed that intervening in Syria could prove to be such a consequential decision—one that could evolve in an unpredictable and dangerous way, consuming the remainder of his presidency—that he was convinced it would be a grave mistake to act in haste and without the country fully engaged in what we were getting into.

As he would later explain in an address to the nation: “I believe our democracy is stronger when the president acts with the support of Congress. And I believe that America acts more effectively abroad when we stand together. This is especially true after a decade that put more and more war-making power in the hands of the president, and more and more burdens on the shoulders of our troops, while sidelining the people’s representatives from the critical decisions about when we use force.”3

For years we had been struggling over what to do about Syria. We had stepped up to the brink of conducting air strikes before, only to pull back. Recent experience had taught us to expect the worst. After a decade that had been dominated by the war in Iraq—a conflict that had begun with promises of easy victory and limited American sacrifices, only to bring terrible costs—the country needed to be in this together. Our eyes were wide open about what might come, and we had concluded the risks were worth it, but we wanted the American people to understand and support our case as well.

Moreover, Obama wanted to make a larger point about the exercise of presidential power and the use of force—something, he later said, he had been “brooding on for some time.”4 Having taught constitutional law before entering politics, he often thought in terms of precedents. He knew that his successors would be measured by his actions.

Since his first presidential campaign, Obama had argued that presidents had the constitutional authority to use force on their own, especially in an instance of a direct threat to America’s security or an immediate emergency like genocide. But in instances in which there was no immediate threat and therefore more time to consider the full spectrum of potential responses (like in Syria), it was always preferable to act with the support of the Congress and with as many allies as possible.5 As Obama said to his aides gathered in the Oval Office debating his decision, he wanted to “break the cycle” of presidents not going to Congress before using force. His recent experience in Libya—in which the US acted without congressional authorization, something I think in retrospect he saw as a mistake—only reinforced this conviction.

So when the president stepped into the sunny Rose Garden that Saturday morning, he announced that he had made two decisions: first, that the US would act against Syria, and second, that he would seek explicit authorization from Congress to do so. “I’ve long believed that our power is rooted not just in our military might,” he said, “but in our example as a government of the people, by the people, and for the people.” With that, the administration set out on a different campaign than the military one we had been preparing for: to convince the American people that intervening in Syria was in the country’s interest.

NOW THAT ALL of Washington had a stake in the decision, the next three weeks were a frenzy of political drama, raucous debate, and second-guessing. Despite Syria having dominated the news for so long, few politicians had thought deeply about it, relieved that it was not their problem. None were happy to share the responsibility of being accountable for what America would or would not do about it. And the foreign policy punditocracy was pirouetting between the wisdom of getting involved in Syria and Obama’s decision to have this debate at all.

What transpired was one of the most revealing episodes in eight years of Obama’s foreign policy. Despite the administration’s strong advocacy and the support from a small minority of hawkish politicians, Congress and the American people proved strongly opposed to the use of force. They did not want to risk getting involved in another conflict like Iraq. In the end, however, the threat of military action ended up achieving something no one had imagined possible: the peaceful removal of most of Syria’s chemical weapons.

Yet, while the outcome unquestionably made America safer, the episode is almost universally seen—by the national security establishment, foreign officials, including those from our closest allies, the media, and even current and former members of the administration—as one of Obama’s most consequential mistakes, an enduring symbol of his foreign policy failures. That the outcome and the interpretation should be so at odds reveals how poorly understood foreign policy is once it is reduced to politicized sound bites and ninety-second news items. They simply eliminate the complexities of the problem and the knotted history that has created it.


Since the Syria crisis erupted in 2011, what to do about its massive chemical weapons stockpile was one of the most perplexing—and scariest—issues the Obama administration faced. At over 1,300 metric tons spread out over as many as forty-five sites in a country about twice the size of Virginia, Syria’s arsenal of chemical weapons was the world’s third-largest. It was ten times greater than the (erroneous) CIA estimate in October 2002 of Iraq’s chemical weapons, and fifty times more than Libya declared in late 2011. Since the Syrian regime denied it even possessed these weapons, what we knew about them came from intelligence gathered by the US and others. But often these were just informed guesses, so we could never be sure of the stockpile’s scale (which we thought could even be larger) or level of security.

Among the many concerns emanating from the Syrian catastrophe, chemical weapons dominated our attention. We worried whether Assad would use those weapons against his own people. We thought he might lash out and use them to attack an ally like Israel. And we were perhaps most focused on the possibility that the weapons would get in the hands of extremists who were gaining strength and taking hold of territory inside Syria.

At the White House and Pentagon, we constantly puzzled over how practically to take out the chemical weapons. The scope of the problem made it overwhelming, hanging like a dark shadow over every aspect of our deliberations. On numerous occasions intelligence indicated that such weapons were about to be used or the security of a storage depot was under threat, and the administration would scramble to prevent something from happening. Sometimes that meant talking directly to the Syrian regime to warn it off, or getting the Russians to pressure Assad, or preparing military options. Some of these scares found their way into press reports; many did not.6

This was the context for President Obama’s first utterance about the use of chemical weapons as a “red line” in an August 2012 White House press briefing. The president had been very focused about the disposition of chemical weapons, and had sat through hours of tense briefings on the subject. While he believed the Syrian conflict touched many American interests—humanitarian, regional stability, and the rise of extremists—chemical weapons security was most urgent and directly threatened US national security. So when the president was asked by NBC journalist Chuck Todd about what might happen if there were indications the chemical weapons were insecure or about to be used, Obama spoke openly about his determination not to allow the weapons to be used or end up in the wrong hands.

“That’s an issue that doesn’t just concern Syria,” he warned. “It concerns our close allies in the region, including Israel. It concerns us.” The president said he had made very clear to Assad and others that “a red line for us is [when] we start seeing a whole bunch of chemical weapons moving around or being utilized.” He further described it as something that would “change my calculus” regarding the use of force.7

Obama considered this a statement of fact rather than a new policy declaration—this wasn’t the conclusion of a policy process or formal decision. In diplomacy, there is always a danger in thinking out loud. Some of his aides were surprised that he went as far as he did—I was one. The president’s statement was undeniably true—if chemical weapons were used it would be a game-changer, regardless of whether he had publicly called it a red line or not—but we had not yet fleshed out a plan to enforce such a threat. In the months that followed, we scrambled to develop our military plans and establish the legal rationale for action.

As the August 2012 statement became widely interpreted as a sacrosanct commitment to act militarily rather than a self-evident analytical comment—therefore turning every stray report of Syria crossing the red line into a dramatic test of US resolve—Obama surely came to regret that he had taken the bait and uttered it in the first place. It serves as another reminder why it is never wise for a president to answer a hypothetical question.8

BY THE SPRING of 2013, concerns about Syria’s chemical weapons had reached a fever pitch. There had been a steady stream of reports about chemical weapons use on a small scale, and importantly, solid intelligence with corroborating soil and blood samples. Mindful of the lessons of Iraq, the administration pressed the intelligence community for greater specificity. But we were careful to give intelligence analysts the space to make their conclusions—we all remembered that the Bush team had been accused of pressuring the intelligence community into concluding that Saddam had chemical weapons to justify intervention in 2003, and no one wanted to repeat that mistake.

The Israelis were especially worried. Syria’s massive arsenal had been designed for use against them. So while they stayed quiet over most aspects of the Syria conflict (as long as the unrest did not turn on them) they had become very agitated about the security of the chemical weapons. The essence of Israel’s military doctrine is to possess the capability to eliminate any threat by itself, yet Israeli defense officials had no answer to the threat of Syria’s chemical arsenal. Of their many security concerns, this was their highest priority.

During a visit to the Israeli Defense Ministry at that time, I met with their senior official in charge of defending against weapons of mass destruction, who explained how they were distributing gas masks and antidotes to every Israeli citizen.9 To address these concerns, the US had increased information sharing with Israel about the whereabouts and security of Syria’s chemical stockpiles, and we started joint contingency planning about what we might do if such weapons got on the loose.

Israeli Prime Minister Benjamin Netanyahu was seized with the issue. He used his first meeting with the new secretary of defense, Chuck Hagel, in April 2013, to make a strong case for action. Meeting in his Jerusalem office, I recall Netanyahu raised his usual concerns about Iran and Hamas, yet at that moment he was most animated about Syria.

Nearly leaping out of his chair, the prime minister said we needed “to think outside the box,” even suggesting that together the British, Americans, and Israelis should divide responsibility for securing each of Syria’s estimated forty-five chemical weapons sites. I remember he urged us to discuss what we could do specifically—such as mining the sites to make them too dangerous to enter, seizing them with special operations forces, or destroying them with airstrikes. Although most of this seemed a bit too creative and we did not pursue any of these ideas with the Israelis, Netanyahu’s stern message to us was clear. We knew we’d have to do something. The question was when and how.

THE NETANYAHU MEETING coincided with an ominous milestone in the Syria conflict. On April 25, the White House announced for the first time that the intelligence community assessed the Syrian regime had used chemical weapons on a small scale. With the red line crossed, the question of what we would do about it surged front and center.10

None of the options were appealing. This was a stark example of the fact that for many foreign policy problems, the choice is not between bad and good, but bad and worse. The challenge seemed so massive and complex that it was hard to know where to begin. At a White House meeting to discuss military actions, one senior Pentagon colleague remarked that “Iran is a tough problem, but it pales in comparison with Syria.” The storage facilities were dispersed throughout the country, and there didn’t seem to be any way to secure them without putting boots on the ground. Military planners estimated that this could take as many as 75,000 troops. The sites would be hard to blow up safely from the air, and we worried about the toxic chemical plumes airstrikes could create.

To the president’s critics, the decision was a no-brainer. With the red line crossed, they wanted America to act immediately, and to them Obama’s caution was more inept than prudent. In March 2013, the top two senators on the Armed Services Committee, Arizona Republican John McCain and Michigan Democrat Carl Levin, urged the president to use precision strikes to destroy Assad’s aircraft and SCUD missile batteries.11 The conservative commentator Charles Krauthammer urged Obama to establish a no-fly zone by destroying Assad’s air defenses.12 And Hillary Clinton’s former director of policy planning (and my former boss) Anne-Marie Slaughter took to the pages of the Washington Post to argue that “standing by while Assad gasses his people will guarantee that, whatever else Obama may achieve, he will be remembered as a president who proclaimed a new beginning with the Muslim world but presided over a deadly chapter in the same old story.”13

The media joined the bandwagon as well, constantly peppering administration officials with questions about why they weren’t intervening, almost taunting them to do so. But this seemed all part of another same old story: once we did act, and things would not improve and in fact might get worse, the mood in favor of action would likely shift. As one White House official described at the time, “The pressures on us to intervene now are enormous. But the day after you do something, the pressures go in the other direction.”14

THIS CONTRADICTORY AND thankless dynamic—clamoring for military action, then expressing outrage that you are actually (or even considering) doing so—characterized the intense congressional debate about using force in Syria in September 2013, following the large-scale chemical attack.

Always mindful to protect their constitutional powers, congressional leaders initially praised the president’s decision to ask for their support. But as public opinion polls showed most Americans skeptical of using force, the mood on the Hill quickly soured. Phone calls were pouring into congressional offices to urge a vote against action. A survey by the Pew Research Center at that time found that 48 percent of the public opposed air strikes against Syria; just 29 percent supported them.15

Immediately after the president’s Rose Garden announcement, teams of administration officials flooded Capitol Hill to brief members and their staffs on all aspects of the issue—from the specifics of the attack and everything we knew about Syria’s chemical weapons program to the types of targets we would hit and the kinds of weapons we would use. Members of Congress were suddenly very worried about the risks. They wanted to know for sure that using military force would work, that once we destroyed the sites the chemical weapons would be kept secure, and that Assad would not retaliate against our troops or allies like Israel.

They demanded answers to questions to which there were no certainties. Although we were confident the planned strikes would affect Assad’s thinking, we could not guarantee it—nor could we say for certain what might happen next. The best we could offer was that we believed the strikes would degrade some of Assad’s capabilities and deter him from acting again. We could not promise that a military response would solve the problem. In fact we had to prepare for the possibility that it may backfire.


  • “Derek Chollet defines and explains the Obama foreign policy as grand strategy. The Long Game goes against the conventional wisdom of our moment. Though an insider's account, it views the present as history and puts down a marker that will shape how historians interpret the Obama years.” –George Packer, author of The Assassins' Gate and The Unwinding

    “Foreign policy in the 21st century requires realism mixed with an element of idealism in order to navigate the intensifying anarchy of the world system. Derek Chollet shows this philosophy in action in this terrifically brisk, insider account of the Obama Administration's travails in the Middle East, Asia, and Europe. Agree with it or not, I know of no more compelling defense of Obama's record.” –Robert D. Kaplan, Senior Fellow at The Center for a New American Security and author of In Europe's Shadow: Two Cold Wars and a Thirty-Year Journey Through Romania and Beyond
  • “Derek Chollet offers a well-argued and convincing defence of President Obama's approach to the world. Chollet is an example of the kind of scholar-policymaker that is such a feature of American statecraft…Chollet's detailed and knowledgeable discussion of the policy options provides a revealing picture of the nature and complexity of the US's policy dilemmas.”—Gideon Rachman, Financial Times

    “[Derek Chollet] is likely to be the closest anyone will come to understanding the thinking behind a foreign policy that has many critics…”—The Economist

    “A measured insider's account of President Barack Obama's foreign policy…[Chollet] relies on his heavyweight credentials and personal perspective in a spirited, thoughtful defense of how Obama responded to both George W. Bush's missteps and the spiraling chaos that has greeted his own goals…A cogent, detailed policy review.” —Kirkus Reviews

    “Chollet has laid out a clear and compelling picture, and his text is positioned to become one of the definitive summaries of the Obama approach.” —National Interest

On Sale
Jun 28, 2016
Page Count
288 pages

Derek Chollet

About the Author

Derek Chollet is counselor and senior advisor for security and defense policy at The German Marshall Fund of the United States, an advisor to Beacon Global Strategies, and an Adjunct Senior Research Scholar at Columbia University’s Saltzman Institute of War and Peace Studies. From 2012 – 2015, Chollet was the U.S. Assistant Secretary of Defense for International Security Affairs, where he managed U.S. defense policy toward Europe (including NATO), the Middle East, Africa, and the Western Hemisphere.

Chollet has also been a fellow at The Center for a New American Security (CNAS), the Brookings Institution, the Center for Strategic and International Studies (CSIS), and the American Academy in Berlin. He has been a visiting scholar and adjunct professor at The George Washington University and an adjunct associate professor at Georgetown University.

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