My walk-and-talk with Richard Holbrooke started in his office at the the State Department’s headquarters in Foggy Bottom, then moved into the hallway and up to the seventh floor and the secretary of state’s ornate, wood-paneled office. It was early 2009, and President Obama had recently appointed Holbrooke as his special representative for Afghanistan. He moved briskly through the entire conversation, only occasionally making eye contact, aides hurrying after him and handing him papers. He paused my answers frequently to take calls on his BlackBerry. This was not real-life government, where meetings are seated and staid. This was government as dramatized by Aaron Sorkin.
Holbrooke was a diplomatic giant, whose service dated back to his years as a young Foreign Service officer in Vietnam, and who had brokered peace in Bosnia in 1995. But he always struck me as vast in other ways—not so much taller but somehow more expansive than his six-foot, one-inch frame. He had pale eyes and a gaze like a bird of prey, but also an irrepressible twinkle, his thin lips always on the verge of a smirk. His eruptions of temper were legendary, but he would just as often go still, dropping his voice to a near whisper. He deployed both tactics in a singular negotiating style he compared to “a combination of chess and mountain climbing”—flattering, bullying, charming and intimidating his way to persuasion. He was oblivious to social graces in the pursuit of his goals. While making an impassioned point, he once followed Hillary Clinton into a women’s room—in Pakistan, she would stress in the retelling. But he was a detailed observer of the world and indomitable in his excitement about it. In other words, he was the rare asshole who was worth it.
Holbrooke and I, along with Frank Archibald, a veteran CIA officer Holbrooke was also lobbying to join his team, met with Clinton, then serving as Obama’s newly minted secretary of state, in the antechamber outside her office. Holbrooke outlined a dazzling vision for the roles we’d play. Repackaged and artfully marketed by him, every underling was a one-person revolution. Archibald was going to single-handedly heal suspicions between State and the CIA. I was going to realign American assistance to NGOs. Another team member, I heard him say on numerous occasions, had written the Afghan constitution. (As he worked up a particular lather about this at one function, she leaned in and whispered in my ear: “I did not write the Afghan constitution.”)
None of us had any business interviewing with the secretary of state for our jobs, but many of us did, through dint of Holbrooke’s willpower. Holbrooke had leaned on the patronage of great men himself, from Scotty Reston at the New York Times to former Secretary of State Dean Rusk and diplomat Averell Harriman. He wanted to be the man that people would say was that kind of man, and he was.
Later, when the interview moved from the State Department to Holbrooke’s Georgetown townhouse, he headed upstairs—not asking, naturally, just carrying on with the conversation. He left the bathroom door ajar and peed. “What about negotiations with the Taliban?” he asked demurely.
“Really?” I said.
“What?” he replied innocently from behind the bathroom door, as if this were the most normal thing in the world. And for him, it was: everyone, including Clinton, seemed to have a story about Holbrooke meetings in bathrooms. He poked his head out, unbuttoning his shirt. “I’m going to hop in the shower.” I stood outside the door. The job interview continued over the hiss of the water.
When Holbrooke’s assignment in the Obama administration first leaked in December 2008, the role was framed as “a special envoy for India, Pakistan and Afghanistan.” This was not sloppy reporting. Though his mandate was ultimately downsized to include only the latter two countries, Holbrooke had initially envisioned sweeping, region-wide negotiations. “Afghanistan’s future cannot be secured by a counterinsurgency effort alone,” he wrote in 2008. “It will also require regional agreements that give Afghanistan’s neighbors a stake in the settlement. That includes Iran—as well as China, India and Russia. But the most important neighbor is, of course, Pakistan, which can destabilize Afghanistan at will—and has.” In Bosnia, Holbrooke had juggled similarly fractious parties: not only Bosnian Muslims, Croats and Serbs, but also Russia, the European allies and organizations like the U.N. and NATO. Here, he again saw a need for a grand, strategic approach.
This ambitious plan for another Mission: Impossible–style political settlement built on old-school diplomacy quickly collided with the realities of the new administration.
He began assembling a crack team that would grow to include officials detailed from across the government. There were representatives from USAID and the Department of Agriculture, the Treasury and the Department of Justice, the Pentagon and the CIA and the FBI. Then there were the outsiders—counterculture thinkers drawn from civil society, business and academia. Vali Nasr, the Iranian-American scholar of Middle East studies, had received a midnight text in December. It was characteristically theatrical: “If you work for anyone else, I will break your knees.” And then, anticipating Nasr’s preference for an Iran-focused job: “This matters more. This is what the president is focused on. This is where you want to be.”
Barnett Rubin, a New York University professor and authority on Afghan history and culture, got a call as well. Rina Amiri, an Afghan activist who had worked with the U.N., recognized Holbrooke on a Delta shuttle from Washington, D.C., to New York and began pressing him about the upcoming Afghan elections. Holbrooke was impressed, and told her he was assembling a team. “I know,” she said, “but I’m here to lobby you.”
“I’m very efficient,” he said. “I just turned your lobbying into a job interview.”
Many of those Holbrooke wooed hesitated. Amiri, worried about her outspoken views on human rights being muted, held out for a month. Rubin made it a condition that he be allowed to keep his academic perch at NYU part time.
I myself wasn’t convinced. I had first worked for Holbrooke in 2004, when he was throwing his weight behind John Kerry’s failed bid for the presidency. That I was far too young for any of it—a teenager, during that earliest internship—never seemed to faze him. It made sense: He himself had perfected the art of being too young and outspoken for his station, pushing back against military escalation in Vietnam during his early days there. Holbrooke let me in, and I was green enough to think nothing of it.
But joining the State Department wasn’t a glamorous career move. “I would go to Davis Polk,” one law school classmate wrote to me, referring to the law firm where I had a job offer. “What is the point of these technocratic positions? Do you really want to spend 40 years trying to move your way up? If you work really hard you might end up where Holbrooke is himself, which is a whole lot of nowhere, really.”
Nevertheless, Holbrooke brought to every job he ever held a visionary quality that transcended practical considerations. He talked openly about changing the world. “If Richard calls you and asks you for something, just say yes,” former Secretary of State Henry Kissinger once said. “If you say no, you’ll eventually get to yes, but the journey will be very painful.”
We all said yes.
As the new administration assembled, Obama ordered a sweeping review of America’s role in Afghanistan and Pakistan. The fundamental question: how many troops to deploy and when. The military had already requested a surge of 30,000 troops when Obama began his term, and during the review, military leaders fought tooth and nail for a fully resourced counterinsurgency, with as many troops as possible, as fast as possible, to remain as long as possible. Holbrooke was nominally the co-chair of the review process, along with retired CIA veteran Bruce Riedel and, according to Riedel, CENTCOM commander Gen. David Petraeus as an “unacknowledged third co-chair.” But Holbrooke was sidelined—by Riedel, who had greater access to the president, by a series of generals, and by the White House itself.
Holbrooke was no dove. At the outset of the review, he had endorsed an initial deployment of troops in advance of the Afghan elections as a stopgap. But he felt military engagement should be organized around the goal of achieving a political settlement. He was alarmed by the force of persuasion the military voices at the NSC table commanded, sometimes crowding out nonmilitary solutions. “I told David Axelrod that we had been dominated much too long by pure mil-think,” he said later. “Military thinking and military domination. And while I had great respect for the military, uh, and Petraeus was brilliant, I liked them as individuals and they were great Americans, they should not dictate political strategy, which is what’s happening now.”
Advocates for a full troop surge were more numerous and had better access than voices of caution. Riedel rode on Air Force One with the president, and briefed him without others present. Secretary of Defense Bob Gates supported his generals and their lobbying for a robust troop surge. Retired General Jim Jones, the national security adviser, did as well. So did his deputy in charge of Afghanistan, Retired Lieutenant General Doug Lute. Holbrooke, with his lessons from Vietnam and his history of loyalty to the kind of Washington, D.C., establishment Obama had run against, was less welcome. Holbrooke had begun taping audio diaries of his experiences, with an eye toward history (and a memoir). “In some of the early NSC meetings with the president, I referred to Vietnam and was told by Hillary that the president did not want any references to Vietnam,” he said in one, his voice sounding tired on the scratchy tape. “I was very struck by this, since I thought there were obviously relevant issues.” “He was incredibly unhappy with the way he was personally treated,” Hillary Clinton reflected. “I was too.
Because I thought a lot of what he was offering had real merit and it didn’t somehow fit into the worldview that the White House had.” Holbrooke had allowed himself to be categorized not as someone to be heard but as someone to be tolerated.
A negotiated settlement with the Taliban was the white whale to Holbrooke’s Ahab throughout his time in the Obama administration. Time and time again, he pushed on the subject only to be rebuffed. Holbrooke longed to make his case to the president and lobbied for a meeting, but he never got one.
Instead, he argued for a diplomatic approach with anyone else in the administration he could get to. The toughest nut to crack was the military. Much of the leadership, including Petraeus, who subsequently became commander of U.S. forces in Afghanistan, felt that talking to the Taliban would interfere with their case for military escalation.
In September 2010, Holbrooke sent a memo to Clinton. “TO: HRC, FROM: RCH,” the memo began. “SUBJECT: AT THE CROSSROADS.” Over nine, single-spaced Times New Roman pages, Holbrooke made his case in stark terms. “I still believe that the importance to our national security of Afghanistan, Pakistan, and the region remains as high as ever,” he wrote. “But our current strategy will not succeed.”
In the memo, Holbrooke argued that the United States had missed critical openings for diplomacy, and pointed the finger squarely at the systematic military domination of the policy process.
That concern topped a list of challenges he included. Holbrooke argued that the lack of space for civilian voices, including his own painful freeze-out, had led to an unwillingness to step outside of that military thinking. This, in turn, had led to a failure to pursue broad-based strategic relationships at the moment the United States had exercised maximum leverage, due to its troop presence on the ground. The result was a bleak prognosis. “The best we can achieve in an acceptable period of time is a murky outcome, in which local violence continues but at a much reduced level.” But he still felt he could secure Pakistani buy-in to a regional agreement, and he still felt a deal with the Taliban was realistic—even “one that still protects women from a return to the worst parts of ‘the black years.’”
He was by then already closing in on talks with a high-level Taliban aide named Syed Tayyab Agha (a lifelong Yankees fan, Holbrooke called him A-Rod). Holbrooke was sober. The administration had lost important opportunities. But he wasn’t giving up.
On December 10, Holbrooke arrived late for a meeting with Clinton, her then-deputy chief of staff Jake Sullivan and Holbrooke’s then-deputy Frank Ruggiero. She was waiting in her outer office, a spacious room paneled in white and gilt wood, with tasseled blue and pink curtains and an array of colorfully upholstered chairs and couches. In my time reporting to her later, I only ever saw Clinton take the couch, with guests of honor in the large chair kitty-corner to her. She’d left it open for him that day.
“He came rushing in,” Clinton later said. “And, you know, he was saying, ‘Oh I’m so sorry, I’m so sorry.’” He sat down heavily and shrugged off his coat, rattling off a litany of his latest meetings. “That was typical Richard. It was, like, ‘I’m doing a million things and I’m trying to keep all the balls in the air,’” she remembered. As he was talking, a “scarlet red” flush went up his face, as Clinton recalled. He pressed his hands over his eyes, his chest heaving.
“Richard, what’s the matter?” Clinton asked.
“Something horrible is happening,” he said.
A few minutes later, Holbrooke was in an ambulance, strapped to a gurney, headed to nearby George Washington University Hospital, where Clinton had told her own internist to prepare the emergency room. In his typically brash style, he’d demanded that the ambulance take him to the more distant Sibley Memorial Hospital. Clinton over-ruled him. One of our deputies in the office of the Special Representative for Afghanistan and Pakistan (SRAP) team, Dan Feldman, rode with him and held his hand.
Holbrooke cracked wise until they put him under for surgery. “Get me anything you need,” he demanded. “A pig’s heart. Dan’s heart.”
When they told him about the risky nature of the procedure, he said, “I feel better. Now I know you’re not B.S.-ing me.” When one of his doctors, Jehan El-Bayoumi, made him promise to relax, he quipped, “You have to promise me that you’re going to end the war in Afghanistan.” Variations of the quote received so much coverage that P. J. Crowley, the State Department’s spokesperson, had to take to the podium in the press room and clarify that Holbrooke was joking. But the joke was only that he’d ever ask anybody else to do it.
Three nights later, hundreds of guests packed the Ben Franklin Room at the State Department as Hillary Clinton stood at the lectern where, two years earlier, she’d announced Holbrooke’s role. Foreign ambassadors to the United States were there, along with six members of Obama’s cabinet.
“Ambassador Richard Holbrooke has been a giant of the diplomatic corps for almost 50 years,” Clinton began. “And this week, his doctors are learning what diplomats and dictators around the world have long known: There’s nobody tougher than Richard Holbrooke. He’s a fierce negotiator.” She paid somber tribute to Holbrooke’s staff, and to the dignitaries in attendance. “Now, in a moment,” she said, her voice rising festively, “You will be treated to another holiday delight, a musical performance from the incomparable Marvin Hamlisch and J. Mark McVey!” She stepped aside, revealing a shiny black grand piano behind her. Hamlisch and McVey began to perform an upbeat rendition of “Deck the Halls.” The World Children’s Choir joined in. Bright, TV-style lights set up around the stage cast an antiseptic glare on the proceedings.
Someone had decided that the most appropriate way to handle the annual State Department Christmas party for foreign ambassadors was to merge it with a Holbrooke tribute event. Standing there before the carolers and Christmas tree, I wasn’t sure.
The president arrived and called out our dazed team standing in the crowd from the lectern. “The SRAP team, where are they? Richard recruited them, he mentored them, and I want you to know that, in our meetings, he consistently gave you guys unbelievable credit. He was so proud, and is so proud, of the work that you do.” The foreign ambassadors applauded, murmuring appreciatively in several languages. We stared at the president. Holbrooke would have burst his aorta voluntarily if he’d known it would conjure up these fond recollections.
Three blocks away, Holbrooke lay in an induced coma with his chest cut open. After 20 hours of surgery, he was, the doctors said vaguely, “hanging in there.” The day before the party, they’d performed an additional surgery to restore circulation to his lower extremities. They’d registered a faint pulse in his feet. The condition of his most celebrated attribute—his brain—was completely unknown.
Because they’d kept his chest open, no one was allowed in the room with him, but the team had spent the past three days by the door anyway. We divided hospital duties into two-hour shifts, each taken on by a pair of staffers. The pair on duty would greet the eye-popping luminaries who began arriving to pay tribute. I’d shown in Vice President Joe Biden, Sen. John Kerry and his wife Teresa Heinz Kerry and PBS NewsHour anchor Judy Woodruff. I sat with future Treasury Secretary Jack Lew and Clinton’s chief of staff, Cheryl Mills, as they tried not to look horrified at doctors’ sketches of the torn aorta on a nearby table. People talked in vague terms about Holbrooke “feeling” the “positive energy.” But it felt like a wake.
I had passed my tolerance for grim Christmas carols at the party and returned to my desk on the first floor when Rina Amiri ran in and flung herself across the couch, sobbing. They were taking Holbrooke off life support. I trudged through the night back to the hospital with Rosemarie Pauli, Holbrooke’s tough-as-nails chief of staff, with whom he’d worked since Bosnia. It was bitterly cold, and a high wind had picked up. Street signs rattled. We arrived at the hospital and stood in the lobby as they unplugged him.
Clinton had been on her way from the State Department party to a dinner at the White House when she got the call. She redirected quickly and arrived in time to be with him at the end. Still wearing a double-breasted, silver-and-gold striped jacket with a flouncy Peter Pan collar that made her look like she was gift-wrapped, she stood under the hospital lights and pulled together the weeping team. I handed out tissues. “There’s our NGO guy, always helping,” she managed. “He was the closest thing to a father I had,” I said quietly, surprising myself. She hugged me. For a woman who’d just lost a friend of many years, Clinton was generous. “Well, I don’t know about you,” she told the group, “but I’m going to the nearest bar.”
As snow started falling outside, we crowded into the nearby lobby bar of the Ritz-Carlton hotel. We were joined by a growing group of mourners. Maureen White, the wife of financier and Obama adviser Steven Rattner, opened a tab. Clinton held court. And everyone exchanged stories about the inimitable Richard Holbrooke.
“I really believed that if Richard had lived, we would have been able to present to the administration some kind of peace deal,” Clinton later told me. “I really believe that. I’m not sure they would have accepted it, but with all the work he did, that [Holbrooke’s deputy] Frank Ruggiero did, the meetings that were underway. … I was very hopeful that, with the meeting we’d have at Lisbon, the NATO conference, we’d be able to build on the peace efforts that Richard was leading. And obviously that didn’t happen because of what, terribly, happened to him that December.” And perhaps that’s true.
As we filed out into the night at around 2 a.m., a lone, drunk woman with lank, graying hair called at me from a nearby table. “I know who you are,” she slurred, leering at us. “I know who you all are.”
“Have a good night,” I said, turning to leave.
“Don’t take it too hard, sweetheart,” she called after me. I glanced over my shoulder. She was grinning wide, showing a row of blood-red, wine-stained teeth. “Everything ends.”