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Authors: Derek Chollet

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Many foreign policy pundits seemed to be fixing for a fight with Putin. And given his behavior, such a fight is tempting. Yet as in Ukraine, by acting defensively Putin got himself into a situation that will continue to be costly. “Putin acted in Ukraine in repsonse to a client state that was about to slip out his grasp, [and] he improvised in a way to hang on to his control there,” Obama told Jeffrey Goldberg. “He's done the exact same thing in Syria, at enormous cost to the well-being of his own country.”
9

This is why, in Syria as in Ukraine, Obama has been determined to make America's response to Russia meaningful yet proportional. He doesn't see it as a return to the Cold War of two countries of equal clout or capability, which is exactly the kind of status Putin craves. “This is not some superpower contest,” Obama has said. “And anybody that frames it in that way isn't paying attention to what is happening on the chessboard.”
10

T
HE
O
BAMA ADMINISTRATION
has also grappled with whether to “do more” to enable Ukraine to stand up against Russia. This was the crux of the heated debate over whether the United States should provide weapons to Ukraine that came to a head in 2015.

Simply put, the Ukrainians were outgunned. They suffered severe losses in the early days of the fighting, and with the Russians on the side of the separatists, it was never going to be a fair fight. In the initial days of the crisis the Ukrainians gave the Pentagon long lists of what military equipment they wanted, which seemed to be just about everything—from blankets to fighter jets. When we asked
them to prioritize what they needed, we would often get different answers depending on which officials we spoke with. While we agreed to provide nonlethal support and start training (the latter more important over the long-term), our deliberations became knotted over the question of lethal assistance.

This was one of the few occasions I can recall in the Obama administration in which just about every senior official was for doing something that the president opposed. He had many reasons. Because Russia would simply counter with even more of its own assistance to the rebels, the president was skeptical that providing lethal support would make a huge difference in changing the military balance. And he was most worried that such support would escalate the crisis, only increasing the bloodshed or, worse, giving Putin a pretext to go further and invade all of Ukraine. Such concerns were shared by key European governments, especially the Germans (who were vital to the sanctions and diplomacy) but even the usually hard-line Baltic countries, who feared Russian retaliation.

Obama supported the Ukrainian leaders, yet I think he has never been entirely comfortable with them. In deciding whether the US should do more, he wants to know whether the Ukrainians were truly committed to reform. This was often hard to see. Obama and the new Ukrainian president, the former candy tycoon Petro Poroshenko, had a difficult first meeting in Warsaw in 2014, and his concerns about the Ukrainians were compounded when Poroshenko visited Washington in September 2014 and gave a speech before Congress criticizing the administration for not giving lethal assistance. I remember reflecting at the time that Poroshenko had received some bad advice from his allies in Washington if he thought that the best way to get the administration to do more would be to belittle the support that he was getting.

Obama also worried about the potential unintended consequences of providing lethal assistance. After the MH-17 civilian
airliner was shot down over the skies of Ukraine by Russian-backed separatists in July 2014, killing nearly 300 civilians, Obama privately pointed out that this kind of thing can happen when you provide lethal assistance to a group that you don't entirely control (the same argument applied about whether to support the Libyan opposition in 2011 or the Syrian opposition in 2012).

The president said it was unlikely that Putin intended for a civilian airliner to be shot down, but that his support for the rebels had, in fact, led to it. Obama knew that he too would be accountable for the way that any assistance the US provided would be used. That said, this was not an ironclad rule. At the exact moment in the summer of 2014 that we were carefully considering every last ounce of assistance we'd be providing to the Ukrainians, and whether any of it could risk escalation or misuse, we were vigorously trying to resupply the Kurds in Iraq, another non-state actor, with thousands of tons of ammunition and weapons to assist them in their fight against ISIS.

I came to believe that it made sense to provide Ukraine with some lethal capabilities, such as Javelin anti-tank missiles (although I too was initially worried about escalation, I concluded that the risks were manageable). But at the same time, I never thought providing lethal assistance would be the decisive step that some of the proponents claimed, especially those outside government. Such weapons would take care of some Russian-supplied armor, raising the costs for Moscow and boosting Ukrainian morale. However, given the time it takes to procure and deliver such assistance, as well as the limited quantities under consideration, they would not have altered the military balance substantially.

Sometimes the desire to control escalation went too far, causing the White House to litigate every step we could take to support the Ukrainians. One such episode from the spring of 2014 bordered on the comical. After we had decided to provide non-lethal military assistance to the Ukrainians, the question was how we would get it there. The quickest route would be via military aircraft, but senior
White House officials were concerned that the image of US military cargo planes with their “grey tails” could be provocative to Moscow. After hours of meetings on this subject, we finally decided to transport the materiel by trucking it into Ukraine overland. It seemed a bit too cautious, but problem solved.

A few weeks later, I arrived in Kiev for my first visit to conduct defense talks with the Ukrainian leadership (I flew commercial). After we landed at the airport and were taxiing toward the gate, I looked out the window and was surprised to find sitting on the runway two hulking US Air Force C-17s, with their grey tails in full glory for all to see. It was the communications and security advance team for Vice President Biden, who was scheduled to stop in Kiev a few days later. In all our earnest deliberations back in Washington about how to deliver nonlethal assistance, no one stopped to think that the mere fact the vice president was traveling to Kiev could create the very “escalatory” image that we were supposed to avoid. If the Russians noticed, they didn't care.

C
RITICS ALSO HAVE
clamored for Obama to “do more” to reassure America's Eastern and Central European allies, who justifiably worry that they are next in Putin's crosshairs. These allies know that most of the reassurance measures and the funding for them are temporary. With President Putin expected to stay in office into the 2020s, Europeans want to secure a more lasting American commitment. To be sure, there is more the United States can do here—such as adding to the troops and military capabilities it has already deployed, or making its “persistent” rotational troop presence a permanent one.

But the challenge for President Obama has been—as it will be for his successor—how to do “more” of this while simultaneously addressing other global priorities, especially addressing the security needs in the Middle East and executing the rebalance to Asia amid resource constraints. In the three most important strategic arenas for the
United States—Europe, the Middle East, and Asia—our partners are anxious about the future, and all want more of the US. But they have maximalist desires that are impossible for the US to meet equally. Just as the world is asking for more, the dynamic in Washington leaves us with less. Obama has tried to reassure partners by balancing these competing demands and trade-offs in a way that is sustainable. Once again, doing more of everything is not a strategy.

F
INALLY, THERE IS
the argument that in Ukraine the US has ceded too much control to the Europeans (especially the Germans) and should have asserted more leadership in the diplomacy with the Russians. The United States has been an active and essential player behind the diplomatic scenes. But for at least three reasons, Obama was determined to avoid getting drawn into the direct US–Russian negotiation over Ukraine.

First, he believed that doing so would give Putin exactly the superpower status he wanted. Second, he believed that having the Europeans in the lead would send a stronger message of unity, in particular, because the Europeans had greater economic leverage over Russia. Moreover, having German Chancellor Angela Merkel in charge would increase the chances that the European Union member states would support and sustain tough sanctions, with Germany corralling and pressuring other countries (which is what happened). And third, there was a question of bandwidth. It was hard to reconcile the time and energy required to lead the diplomacy on Ukraine with the demands on the United States elsewhere around the world, especially after ISIS took over much of Iraq and Syria in the summer of 2014. For all these reasons, the division of labor seemed sensible—and most likely to bring the desired result.

T
O SUM UP
, one can see how Obama's response to the Ukraine crisis, Russia's escalation in Syria, and Moscow's challenge generally is
another example of the Long Game. The steps taken so far against Russia have been more robust than those of most of Obama's predecessors when faced with similar circumstances. These moves have been aimed at achieving a sustainable support relationship for Ukraine that will show benefits over time. They have been designed to reassure and bolster our NATO partners in a way that is balanced and sustainable. The US has shown a willingness to let the Europeans lead in diplomacy, while working vigorously behind the scenes to husband its diplomatic resources for other demands around the world.

When comparing Russia's recent behavior in Ukraine and Syria alongside the US approach, one sees two starkly contrasting approaches to wielding influence—and very different perceptions of what it means to be “strong.” With Russia's military incursions, Putin is trying to protect a sphere of influence and create facts on the ground. Yet as Obama has often put it, Syria is not a great “prize,” and Russia's actions leave it reviled and isolated in the region and around the world. The fact Putin “invades Crimea or is trying to prop up Assad doesn't suddenly make him a player,” Obama says.
11
While such actions may create the veneer of strength in the moment, leading some to conclude Obama has been outfoxed and outmanned, it is difficult to argue that Russia's decisions improve its position for the future.

As leaders, Obama and Putin could not be more different. If Putin has his own version of the long game, it is hard to observe. He is no great strategist. He doesn't play chess—he plays checkers, or maybe just rolls the dice, all with an almost cartoonish machismo. Few believe that's a recipe for future success. Yet still critics urge Obama to be “strong” and make the kinds of choices that would cause him to be, well, more like Putin.

CHAPTER 7

PLAYING ALL FOUR QUARTERS

O
f all the issues Obama inherited, he was most determined to test a new approach with Iran. The position the United States found itself in at the beginning of his first term illustrated one of the most troubling of George W. Bush's legacies: by acting in a way it thought “tough,” refusing even to try to talk with Iran, the Bush administration left the US with little leverage and few tools to halt Tehran's efforts toward developing a nuclear weapon. The “axis of evil” rhetoric sounded strong, but had only served to back the United States into a corner.

When Obama came into office, Iran had the wind at its back. There were many reasons: the Iraq War had taken out Tehran's main enemy, Saddam Hussein, only to replace his regime with a sympathetic, Shia-led government. Iran's coffers were flush with oil revenues, which it poured into modernizing its military and projecting its nefarious influence throughout the Middle East. Iran was fueling its main proxies—Hezbollah in Lebanon and Hamas in the Gaza Strip—each of which posed a grave threat to Israel.

Iran's nuclear capabilities were barreling forward unchecked. When the Bush administration came into office in 2001, Iran did not have any centrifuges for enriching uranium, one of the two pathways to make enough nuclear material for a bomb. By 2003, it had around 100 centrifuges, and by 2009, it had over 5,000. Iran denied that this kind of crash development was for weapons, an assertion few believed—after all, it kept most of its nuclear infrastructure hidden from the world in hardened bunkers buried deep inside remote mountains. If Iran got a nuclear weapon, it would be a game-changer for the Middle East, threatening America's closest partners and potentially setting off a regional nuclear arms race. While these concerns were widely shared around the world, most saw the US policy as the main obstacle to addressing the issue.

Without a US-led diplomatic process to pressure Iran to come clean and cease its nuclear weapons activities, Obama found his options limited. Each carried substantial risks: he could gamble that the status quo would lead Iran to change its mind (which we thought was a fantasy); he could accept an Iran with nuclear weapons (which would be deeply destabilizing); he could use military force to set back Iran's program (something we were neither sure would work nor adequately prepared for at the time); or he could try to change the game by trying a new approach (which might not work).

Faced with these choices, the president was determined to make a major push on Iran. Yet while the administration agreed on what it wanted to achieve, the way to get there was very complex, and Obama's strategy shaped nearly every aspect of his foreign policy. Robert Gates accurately describes the diplomatic and military play to deal with Iran's nuclear program as a kind of national security black hole, “directly or indirectly pulling into its gravitational force our relationships with Europe, Russia, China, Israel, and the Gulf Arab states.”
1

THE DUAL TRACK

The US needed to manufacture some leverage, so Obama pursued a “dual track” policy of engagement and pressure. Each part of the strategy was essential to the other, requiring careful choreography and following an intricate logic. It was based on a core assumption: by refusing to try to engage Iran in meaningful discussions, the United States had allowed Tehran to gain the upper hand by portraying Washington as the problem, making it harder to rally the world to bring meaningful pressure.

Therefore, instead of being a sign of a weakness, engagement was the key ingredient to gaining strength: by engaging, the United States would put the onus on Iran and test whether it was serious in proving its nuclear efforts were for peaceful purposes. If it was (which we doubted), all the better, and we could proceed with negotiations. If it wasn't (which we expected), then we would be able to use its intransigence to expose its true intentions. That would give the United States critical leverage to go to our partners—especially in Europe and Russia—to join us in making Iran pay a price for not cooperating. In this way, engagement was a form of pressure required to reposition the US, now giving it the upper hand.

For decades the United States had had its own economic sanctions against Tehran, but without the rest of the world aboard, the Iranians had not felt the pinch. They needed to face a meaningful choice. A higher price might force Iran to change its calculus and come to the table, or it could live in greater isolation with its nuclear ambitions frozen in place. But if that didn't work, then we could fall back on the option of using force—which by then the US military would have had more time to train and prepare for—with greater legitimacy and support because we had first tried the diplomatic route.

This was a quintessential Long Game play—and to use one of the sports analogies Obama likes, it required playing all four quarters of the game. Patience and thick skin were needed to see it through, as critics would pick apart every move and try to throw the strategy off course. Success would not come instantly; with progress coming incrementally, at any given moment it would often be hard to see if the strategy was working or not.

E
NGAGEMENT WAS THE
first step, one Obama took just minutes after being sworn in as president. In his first inaugural address, he offered an “outstretched hand” to foes like Iran. From that point forward, Obama worked to show that the United States was willing to talk, pursuing a series of unprecedented moves. He took to the airwaves and spoke directly to the Iranian people; sent letters to Iran's supreme leader with an offer to improve relations; and for the first time in decades allowed senior diplomats to meet alone with their Iranian counterparts to discuss possible solutions. Predictably, the Iranians resisted such overtures, responding to Obama with their customary anti-American bombast and rejecting steps designed to test their claims about their nuclear program's true intent.

Along with using Iran's belligerence as a way to create leverage, Obama also sought to expose Tehran's deception. For years the US intelligence community had been monitoring the construction of what was suspected to be a secret nuclear enrichment facility deep in a mountain near the Iranian city of Qom. The Iranians had lied about the existence of such a facility, and once the intelligence agencies had enough confidence in their evidence (a process they spent a lot of time carefully completing, lest they repeat their failures in Iraq), the administration decided to blow the whistle.

In September 2009 Obama joined with his counterparts from the UK and France to expose the revelation, sending a shockwave throughout the world and throwing Tehran back on its heels. Even
those who tended to give Iran the benefit of the doubt, such as Russia, were surprised and angered. Exposing Iran's deceptions, combined with Iran's failure to respond to Obama's engagement overtures, had laid the groundwork to increase the pressure.
2

Tom Donilon, the national security advisor who played the central role designing and implementing this approach inside the White House, described this as the “simultaneous multivector pressure strategy.” While this label did not exactly roll off the tongue, it accurately described the diversity and relentlessness with which the United States squeezed Iran as a way to gain leverage.

E
CONOMIC PRESSURE WAS
the key vector. By the end of 2009 the Obama administration had launched an intensive diplomatic effort to impose new international sanctions against Iran. These measures, which Secretary Clinton dubbed “crippling sanctions,” added up to an unprecedented framework of commercial and financial penalties. Imposed with the authority of the UN Security Council, they closed Iran's oil spigot and made it harder for Tehran to conduct business and banking worldwide.

Securing this global consensus took months of painstaking negotiations. Many of America's partners were skittish about taking these steps because of the financial costs they would suffer, in some cases losing billions of dollars in trade. Clinton worked tirelessly on this effort, cajoling and arm-twisting large powers such as Russia and China as well as appealing to smaller countries like Uganda and Lebanon. Looking back, this was the most successful US-led effort to bring the world around such a tough, costly, and risky policy in two decades, since the George H.W. Bush administration built a coalition against Saddam Hussein in 1990.

These steps had a profound impact on Iran's economy, which contracted severely. Inflation spiked by more than 40 percent, and the value of the Iranian currency plummeted. Oil exports fell by more
than half, costing Iran tens of billions of dollars. Foreign investors and big multinational companies fled. Prices skyrocketed. As evidence of this pain, Iran's leadership dropped its usual defiant assertions about their resilience and began to complain about the injustice of such an “economic assault.”

With this achievement, the United States finally had the upper hand. As Clinton later reflected, “During the Bush years Iran had managed to play the world's great powers against one another and avoided serious international sanctions for its misdeeds. The Obama administration changed that.”
3
But leverage from sanctions, however crippling, would not be enough. We needed to add military pressure as well.

O
BAMA HAD ALWAYS
made clear that for the “dual-track” strategy to succeed, the prospect of military force had to be real. “All options on the table” became the shorthand phrase Obama used over and over to make this point. While we hoped that diplomacy and sanctions would be enough to end Iran's nuclear threat, we needed the kind of insurance only military force could provide. The United States aimed to make clear that it could not accept merely “containing” Iran's nuclear threat, but would take necessary steps to “prevent” it. Iran had to understand that if diplomacy failed and they would not give up peacefully, the US military had other ways to take care of the problem.

This was more than a matter of semantics. Iran, and concerned partners like Israel and the Arab Gulf states, parsed each word uttered by the president and every other senior American official, looking closely for any sign of weakness. They wondered whether the leader who was working so hard to get the US out of wars would be willing to risk starting another. Complicating things further, they listened to senior American military and intelligence officials warn of the negative consequences of military action against Iran. While
truthful, such statements planted seeds of doubt about whether the United States would ever pull the trigger.

The president and his senior team went to great lengths to express his resolve to take military action, repeatedly asserting the “all options” mantra. Obama stressed this was not a “bluff.” The United States needed to show its partners in Israel and the Gulf Arab states that it would be there for them. But words of resolve could only take things so far; he knew that the United States had to demonstrate resolve, which started with ensuring it had the military capability in place to execute any option he ordered.

T
HE PROBLEM WAS
that as late as 2010, we were not ready. Although over time the US military could certainly muster the capacity to set back Iran's nuclear weapons ambitions, thus far it had neither readied the capability nor developed the adequate planning and processes to act quickly in the event that the president decided that diplomacy had failed or because something forced our hand (like an Israeli strike). As Defense Secretary Gates recalled, “There had been no discussion in either the Bush or Obama administrations…about momentous decisions that might be required within minutes if serious shooting broke out in the Gulf.”
4

During his first year in office, Obama directed the Pentagon to get ready for such a contingency, making clear that if he ever decided to strike, he did not want to be told it would take months to plan and prepare. Gates also sounded the alarm that the administration needed to think through how it would respond to contingencies such as an Iranian attack on US interests or an Israeli attack on Iran. How would the administration respond to an Iranian provocation? Would it back up Israel if Israel launched a surprise attack? For months Obama's senior team pored over such questions, the result being what the Pentagon called a series of “break glass” plans to handle them.
5

In addition to issues of planning and procedure, we needed to do more to ensure the military option was not an idle threat. This required having operational capabilities both to deter Iran from lashing out and, critically, to destroy Iran's nuclear facilities if so ordered. Maintaining the necessary forces in the region—or military “posture”—required a lot of tough resource decisions. One of the ironies of reducing the American military presence in Iraq was that it became harder to ensure the US maintained enough firepower nearby to deal with Iran. The White House was intensely focused on what we described as “setting the theater,” often pushing the Pentagon to keep certain capabilities—like personnel, ships, and aircraft—in place when they were scheduled to deploy elsewhere. The result was a robust enough force presence to make good on Obama's pledge that he was not bluffing.

Although the administration tended to let the American military presence speak for itself—Obama once said it wasn't “sound policy” to advertise “what our intentions are”—at times we did speak more openly about it to send a message. One important example was a December 2013 speech by then-Secretary of Defense Hagel in Bahrain.

At that time, with diplomacy with Iran getting some traction, we thought it necessary to make clear that nothing had changed in the US military posture and that “all options” remained on the table (in fact, throughout the negotiations, the Pentagon had never been instructed to change anything about its preparations against Iran). So, in an unusual step, the defense secretary specifically itemized the capabilities the US military had in and around the Persian Gulf, including over 35,000 military personnel, the most advanced fighter aircraft, and over forty naval ships (including an aircraft carrier strike group). Even with American forces out of Iraq, withdrawing from Afghanistan, rebalancing to Asia, and facing budget cuts at home, we wanted to show that the United States had some heft near to Iran. This robust footprint—which is significantly greater than what was
deployed in the Middle East before 9/11—also contradicts the notion that the US has “retreated” from the region (and these numbers increased when the campaign against ISIS began in 2014).

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