href="#litres_trial_promo">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