style="font-size:15px;"> In this White House, representatives of the dusty establishment were out of vogue. After a bruising race, Clinton loyalists were even less welcome—especially those with outsize personalities. “I think his whirlwind of activity, um, did cause some raised eyebrows in the White House,” Hillary Clinton said of Holbrooke. “They thought he was going outside the lines of the orderly policy process, the no-drama White House they were trying to run. And it was very painful for me.”
Two days after the election, Richard Holbrooke arrived in Chicago to interview with the president-elect. The meeting, which lasted thirty minutes, was an immediate disaster. According to friends Holbrooke called afterward. Obama greeted him as “Dick”—to which Holbrooke corrected him, saying that his wife, the writer Kati Marton, preferred that he be addressed as “Richard.” “That’s a joke, right?” Les Gelb, Holbrooke’s longtime friend who had involved him in the Pentagon Papers years earlier, recalled telling Holbrooke. “You didn’t really say that, did you?” It wasn’t. He did. Obama was annoyed—and later told several people so. “For some reason, President Obama thought he”—that is, Holbrooke—“had been treating him with some condescension,” Henry Kissinger said. “I do not know whether that’s true. But anyway, certainly Holbrooke had a lot more experience than the new people coming in.” In a sense, these were all characterizations of something simple: this was a job interview, like any other, and Obama just didn’t like the guy.
AMID THE SWEATY SCHMOOZING at the Fairfax on inauguration eve, Holbrooke was laser focused. Hillary Clinton becoming secretary of state was bittersweet, but also a reprieve. He would play a role in the administration. I watched as he and Clinton talked. He whispered in her ear. The two of them laughed. He made sure the assembled crowd saw it.
Clinton was at her most ebullient. The Obamas weren’t coming and she was the focus of every glance and whisper. She and I had attended the same law school, where several antediluvian professors spanned both of our enrollments. We’d met a number of times over the years, and she had always been kinder than she needed to be. Clinton had a preternatural knack for social recall, or at least artfully covering for memories she lacked. She professed to have read some of my foreign policy columns, and asked what I was doing next. I said I was deciding whether to go back to the law firm where I’d been a summer associate. She looked at me hard and said: “Talk to Holbrooke.”
She and Holbrooke had already begun crafting a new role for him, one she would later describe as, “by many metrics,” the most difficult in the administration. “Ever since my experience in Paris in 1968 as a junior member of the Vietnam negotiating team under Averell Harriman and Cyrus Vance,” Holbrooke once wrote, “I had wanted to test myself against the most difficult negotiations in the world.” He would get his wish.
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
