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With that, he stepped out of the Beast and began to work his way down the receiving line. I got out and walked, my bare feet sticking against the worn leather of my shoes, to a spot under the wing of the plane where clusters of people stood, journalists recording the moment for posterity, staff posed for pictures with one another. The scene was entirely familiar to me after flying well over a million miles around the world on this plane, but it was about to disappear forever.
Barack Obama shook the last hand and made his way up the stairs. He always moved with ease, like an athlete playing a basketball game at slightly less than a hundred percent, holding some energy in reserve for the key moments of the fourth quarter. A man constantly in the public eye who hid important parts of himself. Over the last two years, I’d seen him become increasingly comfortable being both himself and the president—in individual moments, singing “Amazing Grace” in a black church that had been targeted by a white supremacist in Charleston; or in policies, ending an approach to Cuba that he had long told me he opposed. This evolution had made him more effective, more interesting, and ultimately more appreciated in these waning days of his time in office. This was one possible and painful answer to the question he had raised in the Beast: We were right, but all that progress depended upon him, and now he was out of time.
For the first time in eight years, there was no trip left to plan. Obama would board the plane as a successful two-term African American president and a vessel for the aspirations of billions of people around the world. But he was about to hand power over to a man who represented every political, economic, and social force that his own identity opposed. One joke that he told in the days after the election expressed his frustration at how this would impact the rest of his life: “I feel like Michael Corleone,” he’d say. “I almost got out.”
I was twenty-nine years old when I went to work for the Obama campaign. From the tarmac in Lima, I could no longer recognize the person who had moved out to Chicago to write speeches and live in a studio apartment with a few scattered Ikea items and a mattress on the floor. The catastrophes of 9/11 and the Iraq War had propelled me there, in search of a better story about America, and myself. I’d spent eight years pursuing it in a windowless West Wing office where I could hear rats scurrying in the ceiling above me and could walk into meetings where the fate of nations was discussed. I’d experienced highs I could never have anticipated, such as walking into the Vatican to tell a cardinal we were normalizing relations with Cuba. I’d suffered lows I couldn’t yet understand, being demonized by the same forces that led to the rise of Donald Trump. Most of all, I’d subsumed my own story into the story of Barack Obama—his campaign, his presidency, the place where he was leading us.
Standing there, I struggled to find some feeling within myself that would sum up what it felt like to watch our country represented abroad for the last time by this man—decent and determined, at times reticent, at others bolder than any politician I’d seen. But watching him make his way up the stairs of the plane, all I could conjure up was a flood of disconnected images from trips past: a sea of humanity waiting to hear him speak in Berlin; a greeting party of drummers in the middle of the night in Ghana; millions of smiling people lining all the routes of our motorcade in Vietnam; the unlikely sight of Havana from the window of Air Force One. The sense of excitement that people had, all those people in all those places, all those faces looking back with hope. That is what I’d been looking for when I moved out to Chicago ten years before. And that, I realized, would no longer greet an American president abroad, so it was hard to feel anything other than tired and sad. I could not remember what I was like when the story began, and I had no idea what I—or the world—would be like after it was over.
There are more stars in the sky than grains of sand on the earth.
Obama reached the top of the stairs, and I thought he might stop for just an extra moment to take it all in, to offer himself some opportunity to mine the kind of thoughts that were racing through my head. But whatever memories were passing through his own head, however he felt about the hundreds of places he’d been as president and the millions of people he’d seen, despite the uncertainty that now awaited, he offered only a routine wave before disappearing through the doorway of the plane and into the journey home.
What if we were wrong?
CHAPTER 1
IN THE BEGINNING
The first time I met Barack Obama, I didn’t want to say a word.
It was a sleepy May afternoon in 2007, and I was sitting in my windowless office at the Woodrow Wilson International Center for Scholars, a D.C. think tank like dozens of others. I was underemployed and debating moving back home to New York when I got a call from Mark Lippert, who was Obama’s top foreign policy aide in the Senate. Lippert was a young guy, like me, and I had come to expect phone calls from him every few days with random taskings; he was working for the most exciting politician to come along in years, and he clearly enjoyed the fact that anyone would take his call at any time.
“Ben,” he said, “I was wondering if it’s not too much trouble for you to come over and do debate prep with Obama?”
I gripped the phone a little more tightly. For the last few months I’d been doing everything I could to work my way onto the Obama campaign—writing floor statements on Iraq, drafting an op-ed on Ireland (“O’Bama”), editing speeches and debate memos. I had never gotten near the man, and I was starting to wonder if my volunteer work would ever turn into anything else.
“When is it?” I asked.
“It’s right now.”
The session was at a law firm a couple of blocks away, and I walked slowly, gathering my thoughts. Like all the work I’d done for the campaign, this felt like some sort of test, only no grade was issued at the end and no one would tell me if I’d passed. When I got there, I was directed to a set of glass doors that led into a large conference room. I could see at least fifteen people around a long table strewn with binders, stacks of paper, and soda cans. Obama was seated at the head of the table with his feet up. Lippert met me at the door, pulled me outside, and told me they were debating whether Obama should vote for a spending bill in Congress that would fund the so-called surge in Iraq. “I thought, why not call the Iraq guy?” he said.
A few months earlier, I had finished working for the Iraq Study Group, a collection of former officials and foreign policy experts who had been asked to come up with a strategy for the Iraq War. My boss at the time, Lee Hamilton, was cochair, along with James Baker. Hamilton was a throwback—a crew-cut Democrat from southern Indiana who had served thirty-four years in Congress. He wasn’t just a moderate—he was a pragmatist who approached government without a trace of ideology. Baker was what the Republican Party used to be—a business-friendly operator who took governing as seriously as making money. Throughout our work, in meetings with members of the Bush administration that he’d helped put into power through his efforts on the Florida recount after the 2000 election, Baker’s understanding of the scale of the mess that had been made in Iraq seemed to morph into a kind of paternal disappointment—he’d given the keys to his kids and they’d crashed the car.
For me, the project opened a window into a war that I’d watched unfold with swelling anger. As part of our work, we’d gone to Iraq in the summer of 2006, flying into Baghdad in a cargo plane with a group of servicemembers starting their tour, sitting in silence because the roar of the engine made it too difficult to be heard. I looked closely at the faces of these men and women who would soon be threatened by car bombs and improvised explosive devices, but they betrayed no emotion at all—just blank stares. The plane dropped sharply into Baghdad International Airport, making tight corkscrew turns to avoid antiaircraft fire. We flew in helicopters to the Green Zone. Down below, I could smell burning sewage and see the faces of children looking up at us with vacant expressions.
For several days, we stayed on the em
bassy compound in small trailers. At night, we went to a bar—the Camel’s Back—where contractors got hammered and danced on tables. There were two beds in each trailer and a shared bathroom. A flak jacket was next to each bed in case of incoming mortar or rocket fire. I had the place to myself except for one night when I came back to find a bearded guy, perfectly fit and totally naked, standing in the bathroom. I noticed some neatly arranged Special Forces gear by his bed. We didn’t say a word to each other. When I woke at dawn, he was gone. Years later, I would become familiar with the work that people like him did as I learned about it thousands of miles away in the basement of the White House.
During our stay, we were driven in armored vehicles to lavish compounds filled with gold-plated furniture and thick curtains left behind by Saddam Hussein. We met with Iraq’s political leaders, American military officers, and a mix of diplomats, journalists, and clerics. We heard about violence between Sunni and Shia sects that was killing Iraqis just beyond the walls of the Green Zone—bodies in sewers, family members assassinated, nightmarish stories of group executions. We’d recap at night in James Baker’s trailer, where he’d drink straight vodka in a tracksuit and just shake his head at how screwed up things were. The United States had nearly 150,000 troops supporting the Iraqi Security Forces, but everyone spoke of a series of militias as the main drivers of politics. One American general told us that unless the different sects reconciled, “all the troops in the world could not bring security to Iraq.”
Each night, helicopters brought wounded Americans to a temporary hospital. When we visited, Hamilton spoke to a medic who gave us an overview of the work they did. “My job,” he said, “is to keep these folks alive until we can get them up to surgery.” He explained that our troops wear armor that covers your upper body well; what it does not cover is the lower extremities, nor does it guard against the force of the blasts that can cause trauma to the brain. Were it not for this armor, he said, the American dead in Iraq would be closer to the number of those killed in Vietnam; but for those who survive those wounds, life can become a permanent and painful struggle.
Just being there for a few days showed me how the most pivotal moment of my life had led to moral wreckage and strategic disaster. I moved to Washington in the spring of 2002, as the drumbeat for war in Iraq was sounding louder. I moved because I was a New Yorker and 9/11 upended everything I had been thinking about what I was going to do with my life. I had been teaching at a community college during the day, getting a master’s in fiction writing at night, and working on a city council campaign. On September 11, 2001, I was handing out flyers at a polling site on a north Brooklyn street when I saw the second plane hit, stared at plumes of black smoke billowing in the sky, and then watched the first tower crumple to the ground. Mobile phone service was down and I didn’t know if lower Manhattan had been destroyed. A man with some kind of European accent grabbed my arm and said, over and over, “This is sabotage.” For days after, the air had the acrid smell of seared metal, melted wires, and death.
I wanted to be a part of what happened next, and I was repelled by the reflexive liberalism of my New York University surroundings—the professor who suggested that we sing “God Bless Afghanistan” to the tune of “God Bless America,” the preemptive protests against American military intervention, the reflexive distrust of Bush. I visited an Army recruiter under the Queensboro Bridge. After leaving with a pile of materials and getting a few follow-up phone calls, I decided that I couldn’t see myself in uniform. Instead, I would move to Washington to write about the events reshaping my world. I had never considered being a speechwriter, and I had never heard of Lee Hamilton, but one reference led to another and soon I found myself at the Wilson Center, one small cog in the vast machinery of people who think, talk, and write about American foreign policy. I was a liberal, skeptical of military adventurism in our history, and something seemed off about toppling Saddam Hussein because of something done by Osama bin Laden. But when you’re putting on a tie and riding the D.C. metro with a bunch of other twenty-five-year-olds to a think tank a few blocks from the White House, angry about 9/11 and determined to be taken seriously, you listen to what the older, more experienced people say. The moment Colin Powell made his case for war to the United Nations, I was on board.
Now here I was, a few years later, seeing what that war had wrought. We began writing the Iraq Study Group report by committee, but after a few drafts, Baker’s staff guy called me and asked me to take the lead. I’d stay up all night agonizing over sentence structure and whether the group was going far enough in calling for an end to the war. The first sentence of the report said “the situation in Iraq is grave and deteriorating,” and the report called for a phased withdrawal of U.S. troops. Instead, Bush put more troops into the country. To me, the experience clarified two things: First, the people who were supposed to know better had gotten us into a moral and strategic disaster; second, you can’t change things unless you change the people making the decisions. I had a decent policy job, but I wanted to get into politics. And I wanted to work for Barack Obama.
Lippert and I walked into the conference room, and I took a seat near the back end of the table farthest from Obama. From the moment I saw his speech at the Democratic convention in 2004, I had wanted him to run for president. He had been against the war when nearly everyone else went along with it. He used language that sounded authentic and moral at a time when our politics was anything but. There was also something else, something intangible. The events of my twenties felt historic, but the people involved did not. I wanted a hero—someone who could make sense of what was happening around me and in some way redeem it.
I was seated next to Tony Lake, who—along with Susan Rice—was leading a network of foreign policy advisors for the campaign. Lake was a soft-spoken older guy with the smart but slightly scattered demeanor of a professor at a small liberal arts college, which he’d been for many years. He’d also been Bill Clinton’s first national security advisor. Rice had also worked for Clinton, becoming the assistant secretary of state for Africa. Since then, she’d been a leading Democratic voice on foreign policy—unabashedly ambitious, well-spoken, and prolific—who risked her relationship with the Clintons to work for Obama. Still, over the last few months, I’d come to suspect that the network led by Lake and Rice was mostly about giving people a way to feel connected to a candidate they were unlikely to ever meet. Most of the work I’d done that actually reached Obama was coordinated by Lippert and another campaign staffer, Denis McDonough. It was Lippert, after all, who had brought me into this room.
David Axelrod was the principal strategist, and as I took my seat he was giving a long description of the political dilemma—Democratic primary voters would want any vote on the Iraq War to be a no, but if Obama voted no, a future Republican general election candidate would say that Obama failed to fund our troops in battle. The ghosts of the 2004 election, when Republicans painted John Kerry as soft on terrorism, lingered in the room. “I’m sure they’re having the same discussion in the Clinton campaign,” Axelrod said.
“Hillary will vote however I vote,” Obama said. I was struck by his confidence; it could have seemed like arrogance, except he was so casual in his tone.
The conversation meandered around the room. Most everyone was neutral—describing the dilemma, as Axelrod did, but offering no clear recommendation. It felt as if the political advisors leaned no but didn’t want to say so. When it got to Susan, she made the case for voting yes. Compact, permanently composed, and the only African American in the room other than Obama, she spoke in sharp, declarative language. “This is about the bullets that go in the weapons that defend our troops,” she said. “This is a commander in chief moment.”
As she spoke, I felt panic welling up inside me. I didn’t want to be called on. At the time, I had a profound fear of public speaking. If a group was familiar to me, I didn’t have a problem. But here, I wouldn’t be abl
e to conceal my nerves. I imagined myself staring blankly, then choking on my words. There, at the head of the table, was Barack Obama. What would he think if I couldn’t get through a paragraph of advice?
To avoid having to speak in front of the group, I figured I’d give Lake my views. I leaned over and began to tell him why I thought Obama should vote no. Obama, a former law professor, has a trait that I would witness thousands of times in the years to come. He likes to call on just about everyone in a room. And he doesn’t like it when people have side conversations. “Tony,” he called out from the other end of the table. “You have a view you want to share?”
“Why don’t we ask Ben?” Tony said.
“Who’s Ben?” Obama asked.
“He helped write the Iraq Study Group report,” Lippert said.
“Well, what do you think?” Obama looked at me. Nerves in my stomach became tightness in my chest, dryness in my throat. There was no way I could speak in paragraphs. So I had to do something different that would break up my speaking.
“Well,” I said. “You oppose the surge, right?”
“Sure,” Obama said. I took a deep breath.
“And you’ve introduced legislation to draw down our troops in Iraq and impose more conditions on the Iraqis to reconcile, right?” I asked.
“Yes,” Obama said.
“And this legislation funds the surge and rejects your plan, right?”
“Yes.”
Obama seemed to be getting irritated, so I got to the point. “Well, why would you vote to fund a policy that you oppose, that you don’t think will resolve the situation in Iraq, and that contradicts the legislation that you’ve introduced? You should vote no.”
The room was quiet for a moment. Obama leaned forward and tapped the table with his hand. “Okay, I think we’ve talked about this enough,” he said. “I’ll make a decision when I go up to the Hill.”