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WHEN HOLBROOKE’S ASSIGNMENT first leaked, 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 UN 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. Two days after the parties on inauguration eve, Holbrooke stood in front of a crowd of current and former diplomats in the Benjamin Franklin State Dining Room, the grandest ceremonial chamber on the State Department’s eighth floor. The room was renovated in the 1980s in a classical style meant to evoke the great reception halls of continental Europe. Ornate Corinthian pillars, clad in red plaster and painted with faux-marble veins, lined the walls. Portuguese cut-glass chandeliers hung around a ceiling molding of the Great Seal of the United States: a bald eagle, one set of talons grasping a bundle of arrows, the other an olive branch. Holbrooke was flanked by Barack Obama and Hillary Clinton on his right, and Joe Biden and the administration’s newly appointed Middle East peace envoy, George Mitchell, on his left.

“It’s an extraordinarily moving thing for me to return to this building again, having entered it so many years ago as a junior Foreign Service officer,” he began. In Afghanistan, he described a war gone wrong; in Pakistan, a challenge “infinitely complex.” He thanked the president for paying tribute to diplomats on his second day in office, and Obama, in turn, stressed his “commitment to the importance of diplomacy” and his recognition “that America’s strength comes not just from the might of our arms.” Those convictions were tested during his eight years in office.

Holbrooke looked out at his wife, Kati, his sons David and Anthony, and colleagues he’d known across decades. He seemed emotional, his voice wavering. “I see my former roommate in Saigon, John Negroponte here,” he said. “We remember those days well, and I hope we will produce a better outcome this time.” The audience laughed. Obama was expressionless.

While other regional initiatives being announced by the new administration were headed by “envoys,” Holbrooke, in what was to be one of many annoyances for the White House, insisted that he be given a sui generis title: “Special Representative.” It was, in his view, a more concrete managerial term than “envoy”—a way to signal that he was building up a sizeable, operational team.

In 1970, a young Holbrooke had written an article in Foreign Policy, the upstart publication at which he would later become editor, decrying the sclerotic, siloed bureaucracy of the State Department. Returning decades later, he decided to shake things up. He began assembling a crack team with 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 UN and Open Society Institute, recognized Holbrooke on a Delta shuttle from DC 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.”

My own interview was, likewise, distinctive.

“WHAT SHOULD WE BE DOING DIFFERENTLY?” Holbrooke shouted over the hiss of the shower he was taking in the middle of that job interview. From the next room over, I laughed. I couldn’t help it.

It was the culmination of a sprawling, hours-long meeting, which had ranged from his office, to the secretary of state’s, to his townhouse in Georgetown. I had followed up on Clinton’s advice at the preinaugural party at The Fairfax and begun talking to Holbrooke and his chief of staff, Rosemarie Pauli. A little over a month later, in March 2009, I arrived at the State Department to meet with him in person. He barreled out of his office, lobbing policy questions at me. How would I reinvigorate trade in Central Asia? How would I maximize the impact of assistance to the Pakistanis? Never mind that I was a wet-behind-the-ears lawyer, with a modest foreign policy background in Africa, not Afghanistan. I’d worked with local nongovernmental groups in the developing world, and Holbrooke wanted to ramp up the United States’ emphasis on those groups—a change of culture in a war zone where most of the implementation happened through powerful American contractors. He wanted nontraditional answers, unencumbered by government experience.

The State Department, in DC’s Foggy Bottom neighborhood, is an imposing slab of stripped classical architecture, clad in limestone and built, in portions, in the 1930s and 1950s. The earliest part of the complex was intended for the growing War Department after World War I, though with the construction of the more ambitious Pentagon, it never actually became the military’s headquarters. The looming rear entrance to the building is still known as the War Department—a flourish of irony, for the seat of American peacemaking. The Department is a literal hierarchy, with opulent ceremonial rooms for receiving foreign dignitaries on the eighth floor, the secretary’s office on the seventh, and offices of roughly descending importance on the floors beneath. During Holbrooke’s prodigious turn as assistant secretary in his mid-thirties, he had occupied an office complex on the sixth floor. Now, he’d been relegated to the first, next to the cafeteria—where Robin Raphel was later deposited, and across the hall from the Department newsstand, where Holbrooke would load up on junk food between meetings.

Our walk-and-talk started in his office and moved into the hallway, then up to the seventh floor and the secretary of state’s ornate, wood-paneled office. 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 and I, and a veteran CIA officer Holbrooke was also lobbying to join his team, Frank Archibald, met with Clinton briefly in the antechamber outside her office. He outlined a dazzling vision for the roles we’d play. Repackaged and artfully marketed by Holbrooke, 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. Amiri, 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 Times to Dean Rusk and Averell Harriman. He wanted to be the man that people would say was that kind of man, and he was.

After meeting with the secretary, we had returned to Holbrooke’s office suite on the first floor, where he’d picked up his luggage. He had just returned from a trip and had to go home to change before an afternoon meeting at the White House. He passed me a suitcase and out we went to hail a cab, not interrupting the flow of questions. Would I favor more overt United States branding on USAID assistance in the region? How would I enlist local watchdog groups in ensuring electoral transparency? I had just recovered from several years in a wheelchair, the result of a bone marrow infection left untreated while working in Sudan. Holbrooke was aware of this but characteristically oblivious to it in the moment. I hobbled after him with his luggage. When we arrived at his Georgetown town house, 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—virtually everyone 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.

Many Holbrooke wooed hesitated. Rina Amiri, worried about her outspoken views on human rights being muted, held out for a month. Barnett Rubin made it a condition that he be allowed to keep his academic perch at NYU part time. I myself wasn’t convinced. 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 forty 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. Fuck that.”

But 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,” Henry Kissinger said. “If you say no, you’ll eventually get to yes, but the journey will be very painful.” We all said yes.

By the summer, Holbrooke had assembled his Ocean’s Eleven heist team—about thirty of us, from different disciplines and agencies, with and without government experience. In the Pakistani press, the colorful additions to the team were watched closely, and generally celebrated. Others took a dimmer view. “He got this strange band of characters around him. Don’t attribute that to me,” a senior military leader told me. “His efforts to bring into the State Department representatives from all of the agencies that had a kind of stake or contribution to our efforts, I thought was absolutely brilliant,” Hillary Clinton said, “and everybody else was fighting tooth and nail.”

It was only later, when I worked in the wider State Department bureaucracy as Clinton’s director of global youth issues during the Arab Spring, that I realized how singular life was in the Office of the Special Representative for Afghanistan and Pakistan—quickly acronymed, like all things in government, to SRAP. The drab, low-ceilinged office space next to the cafeteria was about as far from the colorful open workspaces of Silicon Valley as you could imagine, but it had the feeling of a start-up. The office was soon graced with cameos from eclectic and unexpected faces. Holbrooke hosted a procession of journalists, to whom he remained as close as he had in previous jobs. Prominent lawmakers visited. He met with Angelina Jolie about refugees and Natalie Portman about microfinance. Holbrooke knew what he was doing was counterculture, and he believed it to be historic. There were reminders of his view of our place in history everywhere. Even his office was a shrine to wars that came before. In framed pictures on the walls, there he was, smiling in the Mekong Delta; there he was with Bill Clinton in East Timor, or in Sarajevo flanked by armed guards. “Are you keeping a journal?” he’d ask me. “One day you’ll write about this.”

CLINTON HAD TOLD HOLBROOKE he would be the direct civilian counterpart to General David Petraeus, who was then the commander of US Central Command (CENTCOM), the powerful Pentagon division responsible for Iraq and Afghanistan and Pakistan. “He has more airplanes than I have telephones,” Holbrooke later grumbled. Petraeus was a small man with a wiry physique honed through a daily, predawn workout regimen that had become catnip for profile writers: five miles of running, followed by twenty chin-ups—a torturous modification involving a full leg-raise until his shoelaces toucehed the bar—and then a hundred push-ups. At a 2016 meeting of the shadowy Bilderberg Group in Dresden, Petraeus, by then in his sixties, was accosted by twenty-something-year-old reporters shouting questions. He sprinted away. They tried, and failed, to catch him. He had once taken an M-16 shot to the chest during a live fire training exercise and lived to tell the tale. Legend had it that he ate one meal a day and never slept more than four hours. I once had the misfortune to stand in line at a buffet next to him. His eyes flicked down to my plate of mac and cheese. “I’m … going for a run later,” I offered defensively. He clapped a hand on my shoulder. “Really? Think you can keep up?” (I have never gone for a run in my life.)

Petraeus, like Holbrooke, was a larger-than-life operator who knew how to build a public narrative and use it to his advantage. He too, had the ear of every reporter in Washington, a direct line to the op-ed pages, and a tendency to surround himself with experts who could help propagate his message outside of the government. He was, enraptured profiles noted, a scholar-general, and this was true—he had been an ace student at West Point before receiving a doctorate from Princeton’s Woodrow Wilson School of Public and International Affairs. His doctoral dissertation was titled “The American Military and the Lessons of Vietnam: A Study of Military Influence and the Use of Force in the Post-Vietnam Era.”

Holbrooke and Petraeus both interrogated America’s misadventures in Vietnam, but they came up with diametrically opposed answers. Holbrooke believed counterinsurgency doctrine—or COIN, as it came to be known—was a recipe for quagmire, breeding dependency in local populations. Petraeus believed in the doctrine and built a career championing its revival. In Iraq he relied on a sweeping COIN strategy. Broadly speaking, that meant a large deployment of troops, integrated within Iraqi society over a long period of time, securing communities while getting the bad guys. Petraeus had emerged from that conflict a hero. Critics argued that he benefitted from events outside his control—like al-Qaeda leader Muqtada al-Sadr declaring a unilateral ceasefire. Others contended that his accomplishments fell apart after his departure, or that they were exaggerated to begin with. (That included then-senator Hillary Clinton, who, in a 2007 congressional hearing, accused Petraeus of presenting an overly optimistic assessment of the Iraq troop surge at a time when she was seeking to create distance from her Iraq vote. “I think the reports that you provide to us really require the willing suspension of disbelief,” she said.) But in Petraeus’s view, COIN had worked in Iraq, and for his many ardent supporters in the Pentagon, it became gospel. In Afghanistan, he intended to put COIN to the test a second time.

Shortly after Hillary Clinton accepted Obama’s job offer, she, Petraeus, and Holbrooke sat around the fireplace at her Georgian-style mansion near DC’s Embassy Row and shared a bottle of wine. “I worked really hard to make sure Richard had relationships with the generals,” Clinton said. “I invited him and Dave Petraeus, who hadn’t met each other, to come to my house and to talk about what each of them thought needed to be done.” She knew Petraeus—who had just become commander of CENTCOM—would play a defining role in some of her greatest international challenges.

That night at Clinton’s home marked the first of a series of dinners and drinks between the two men, and the partnership was often characterized as a strong one in the press. “Richard did share Petraeus’s interest in an aggressive counterinsurgency strategy,” Clinton recalled, “but focused on increasing the credibility of the government in Kabul and trying to weaken the appeal of the Taliban. Richard wasn’t sure that adding more troops would assist that, he thought it would maybe undermine goodwill.”

The truth was, Petraeus and Holbrooke were wary of each other. Organized, tightly controlled Petraeus (though, subsequent years of scandal would suggest, not so tightly controlled in some areas) was often uncomfortable with Holbrooke’s freewheeling improvisation. New York Times reporter Mark Landler later recalled Petraeus arriving for a meeting as he interviewed Holbrooke, and Petraeus’s dismay both at Holbrooke’s impromptu suggestion that Landler stay on with the two of them, and at Holbrooke’s shoeless feet propped on a coffee table. “Richard, why aren’t you wearing shoes?” Petraeus asked, horrified. Holbrooke said he was more comfortable that way.

I first met Petraeus at the Kabul headquarters of ISAF—the NATO mission in Afghanistan. I’d presented a PowerPoint (the military loves PowerPoints) on civil society in Afghanistan, and afterwards Holbrooke, in his typical manner of elevating subordinates, introduced me to the general. “So, you’re working for my diplomatic wingman,” Petraeus said, rising from his seat to shake my hand. Petraeus called Holbrooke his “wingman” a lot, in private and in the press. Holbrooke hated it. He didn’t particularly relish being anyone’s wingman. And the power imbalance, and what Holbrooke took to be Petraeus’s ribbing about it, struck a deeper nerve, running against the grain of Holbrooke’s belief that military power should be used to support diplomatic goals. “His job should be to drop the bombs when I tell him to,” Holbrooke told our team testily. Petraeus later told me he intended “wingman” to be a show of respect. But he admitted that the relationship was fraught. “He was a difficult partner at various times. I think he had ADD and some other things. Very difficult for him to stay focused,” he recalled. “Richard came in thinking, ‘I am Richard Holbrooke’ and the administration came in thinking, ‘I am Barack Obama.’ Seriously bright people. But they were supposedly going to be able to do something that nobody else could do.”

AS THE NEW ADMINISTRATION ASSEMBLED, Obama ordered a sweeping review of America’s role in Afghanistan and Pakistan. The process was so torturous that the journalist Bob Woodward managed to spin an entire book out of disgruntled accounts of it. For ten meetings spanning more than twenty-five hours, the president heard arguments and proposals. Countless more meetings were conducted by lower-ranking officials. 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. “We cannot achieve our objectives without more troops,” Petraeus argued. After the very first National Security Council meeting on the subject, he said he was going to move forward on the pending troop surge. White House Chief of Staff Rahm Emanuel had to rein him in: “Hold on,” he said, according to leaked accounts. “General, I appreciate you’re doing your job, but I didn’t hear the president of the United States give that order.”

Holbrooke was nominally the co-chair of the review process, along with retired CIA veteran Bruce Riedel and, according to Riedel, 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. The review threw into sharp relief the generational and cultural chasm between Holbrooke and Obama. In a February 2009 National Security Council meeting, Holbrooke compared the deliberations to those Lyndon Johnson conducted with his advisers during Vietnam. “History should not be forgotten,” he said. The room fell silent. Obama muttered: “ghosts.” When Holbrooke brought up Vietnam again several months later, the president was less demure. “Richard,” he snapped, cutting him off. “Do people really talk like that?” 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.

But the more meaningful divide was with the military. Holbrooke was no dove. He had supported the invasion in Iraq, and at the outset of the review, he 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 in another tape. “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.”

After one meeting, he emerged, exhausted, and told Vali Nasr something absurd: Secretary of Defense Robert Gates had bigger folders. His maps and charts were more colorful. The SRAP team had cranked out voluminous policy papers, but they were going unread by many of the president’s advisers. “Who can make graphics?” he asked in one meeting. Everyone looked at me. “Ageism,” I muttered, and went to work making technicolor PowerPoints out of his policy proposals, which he dictated in minute detail. Often, they focused on political and diplomatic solutions he felt were being given short shrift by the White House. A series of concentric circles showed the complex landscape of global players he felt the United States needed to do more to engage—from international donors, to NATO states, to rising powers like India and China. Triangles linked by arrows illustrated trilateral relations between Pakistan, India and the US. A flow chart, titled “Changing Pakistan’s Behavior Toward the Taliban,” offered a storybook simplification of his plan for the most difficult bilateral relationship in the world:

1 Focus on entire country with new US-led international assistance and new commitments campaign …

2 … Which builds pro-US-sentiment …

3 … Which helps turn the Pakistani government and Pakistani military toward our position …

4 … Which gets Pakistan’s military to take more action against the Taliban and Al Qaeda.

The graphics did little to move the needle. 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 advisor, did as well. So did his deputy in charge of Afghanistan, Retired Lieutenant General Doug Lute. Hillary Clinton, despite her advocacy for Holbrooke, was fundamentally a hawk. “There’s plenty of blame,” Ben Rhodes, the deputy national security advisor, later recalled. Holbrooke’s “biggest defender was Hillary, and yet she constantly sided with the generals in the policy discussions.”

“I was convinced that Richard was right about the need for both a major diplomatic campaign and a civilian surge,” Clinton said. “I did disagree with him that additional troops weren’t needed to make that work, because I thought, given how the Bush administration had kind of lost interest in Afghanistan because of their hyper-concern about Iraq, that the Taliban was really on the upsurge and that there had to be some demonstration that we’d be willing to push back on them.”

Holbrooke had to hold his tongue, but he knew force alone couldn’t solve the crisis in Afghanistan. “My position was very precise,” he said over a meal with Bob Woodward, who recorded the conversation. “I will support you in any position you take cause you’re my boss but you need to know my actual views. I have serious concerns about the fact that our troops are going to be spread too thin and I’m most concerned we’re going to get into a mission/resource mismatch. A lot of people thought I was overly influenced by Vietnam. It didn’t matter to me. At least I had some experience there.”

“I always had such regret about the Holbrooke thing,” Rhodes said. “It went wrong and it feels very unnecessary when I look back.” It was, he reflected, like “Holbrooke was in a game of musical chairs, and he was the guy without a chair to sit in.”

One of the Kafkaesque qualities of the period was the profusion of seemingly duplicative reviews—not just the White House’s process led by Riedel, but prior assessments by Petraeus, and one by Stanley McChrystal, the new general in charge of Afghanistan. Just before McChrystal released his recommendations, Holbrooke told our team exactly how the process would play out. There would be three choices. “A ‘high-risk’ option,” he said, gesturing above eyeline, “that is what they always call it, which will call for maybe very few troops. Low troops, high risk. Then there will be a ‘low-risk’ option,” he said, moving his hand down, “which will ask for double the number they are actually looking for. In the middle will be what they want.” Holbrooke had seen this movie before. The first recommendation of the final Riedel report was for a “fully resourced” counterinsurgency in Afghanistan. After months of dithering, the President chose COIN, and a deployment of 30,000 additional troops.

Obama announced the surge with an expiration date: two years later, in mid-2011, withdrawals would begin. Conspicuously absent from either the Riedel report or the president’s announcement was any commitment to negotiation, either with Pakistan over the terrorist safe havens, or with the Taliban in Afghanistan. There was “no discussion at all of diplomacy and a political settlement,” Vali Nasr recalled. “Holbrooke wanted the president to consider this option, but the White House was not buying it. The military wanted to stay in charge, and going against the military would make the president look weak.”