paragraphs. As oblivious as he could be to the sensitivities of people around him, 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.
As a child, he idolized scientists: Einstein, Fermi. But his interests turned to the wider world. After his father succumbed to colon cancer, he grew close to the family of his classmate, David Rusk, whose father Dean would soon become Kennedy’s secretary of state, and who visited Holbrooke’s class at Scarsdale High School to extol the virtues of the Foreign Service. At the time, it was journalism that captivated Holbrooke. He was sports editor at his high school’s newspaper, then editor in chief of his college’s, the Brown Daily Herald, where his analyses of Cold War tensions ran under announcements for cheerleading tryouts. As a sophomore, he convinced his editors to send him to the 1960 Four Powers Summit in Paris, where Western leaders were set to meet with Nikita Khrushchev to try to ease tensions over the division of Berlin. The summit was a spectacular failure. Days before, the Soviets shot down a U-2 spy plane and the ensuing confrontation soon shut down the talks. James “Scotty” Reston of the New York Times, whom Holbrooke idolized and who gave the young student journalist a job fetching drinks for the Times team in Paris, told Holbrooke: “Whether you go into journalism or the Foreign Service as a career, you will always be able to say, ‘I started my career at the worst diplomatic fiasco ever held.’” He was wrong: Holbrooke would see worse. After graduating from Brown, he tried and failed to get a job at the Times and decided to take the Foreign Service exam. So it was that newly minted Foreign Service officer Richard Holbrooke arrived at Tan Son Nhut airport in Saigon on a muggy June night in 1963.
VIETNAM WAS THE FIRST modern test of American “counter-insurgency”—the strategy of securing a vulnerable population while winning its loyalty through social programs. During a Foreign Service training course, Holbrooke and his Vietnam-bound contemporaries—including Anthony Lake, who would later become Clinton’s national security advisor—whiled away sweltering nights playing a game called “fan ball,” which involved throwing a tennis ball at a ceiling fan, then scrambling to chase it as it ricocheted around the room. (They could hardly have designed a more conspicuous Vietnam metaphor if they tried.) At the time of his arrival, twenty-two-year-old Holbrooke was single and could be sent to the rural frontlines to oversee development programs. It gave him an unvarnished view of mounting failures that his superiors in Washington lacked.
He also witnessed the precipitous militarization of policymaking in Vietnam. During a trip with the 9th Marine Regiment in rural Da Nang, Holbrooke watched General Lewis Walt, commander of the Marine Amphibious Force, kneel and push away semicircles of sand in front of him, showing how the Americans would supposedly push out the Vietcong, making way for the South Vietnamese and good governance. A group of Vietnamese children looked on, chattering curiously. Holbrooke, never one to mince words, pointed out: “But the VC will just move in behind you.” The general, and Americans across Vietnam, kept on pushing for years. “Despite the hours and days of instruction they had in ‘counterinsurgency,’ despite all the briefings which emphasized the political nature of the war, they could not understand what was going on or how to deal with it,” Holbrooke wrote in one unpublished memo. The insurgents would not give up, and the locals “were not going to switch sides in return for some free soap.”
Holbrooke dissented, loudly. During his time in the provinces, he once argued openly with General William Westmoreland, the commander of US forces in Vietnam.
“How old are you?” Westmoreland finally asked, exasperated.
“Twenty-four.”
“What makes you think you know so much?”
“I don’t know,” said Holbrooke, “but I’ve been here two years and I’ve spent all of the time in the field.”
Westmoreland was reporting back to Washington his conviction that he could break the insurgency through increasing levels of force. As Holbrooke ascended to positions at the White House and State Department, he sent vigorous, often unsolicited memos to his bosses. “I have never seen the Americans in such disarray,” he wrote in one when he was just twenty-six. Forty years later, when I was working for him as the military pushed for a troop surge in Afghanistan, Holbrooke unearthed the memo and had me forward it to his Vietnam buddies.
When the Department of Defense launched the top-secret review of Vietnam eventually known as the Pentagon Papers, an official named Leslie Gelb, who went on to become the head of the Council on Foreign Relations and a lifelong friend to Holbrooke, tapped the iconoclastic young diplomat to write one volume. Holbrooke’s contributions were scathing. The counterinsurgency was “faultily conceived and clumsily executed.” The hawks, he argued, had dangerously commandeered policymaking.
When the legendary diplomat Averell Harriman headed a delegation to negotiate with the North Vietnamese, Holbrooke numbed his bosses into submission hustling for a spot on the team. He believed in the power of negotiation to end the war. “Holbrooke wants to always talk with the other side,” said Nicholas Katzenbach, the under secretary of state who was Holbrooke’s boss in the late 1960s. “He always thinks there’s some negotiation, some middle road.” But Paris was an agonizing failure. During a close presidential race, the Nixon campaign, it later emerged, worked to scuttle the talks, encouraging South Vietnam to drag its feet. Famously, the team wasted two months arguing over the shape of the negotiating table, as the war raged.
Shortly after Nixon took office, Holbrooke resigned and left government. “[I]t was neither foreordained nor inevitable that the war should continue, with another twenty-five thousand Americans and countless Vietnamese dead,” he later wrote. “A negotiated end to the war in 1968 was possible; the distance to peace was far smaller than most historians realize.” He’d seen the United States squander one chance to end a war; he wouldn’t let it happen again.
As the war in Afghanistan raged in September 2010, the State Department Historian’s Office released the final volume in the government’s official history of Vietnam. Richard Holbrooke walked from his office to the State Department’s George C. Marshall Conference Center to deliver remarks on the publication, which contained one of his early memos. It was a gray day, and he wore a gray, rumpled suit, and stood in front of a gray drop cloth. The fluorescent lights cast deep shadows under his eyes. He paused a little more often than usual. When an audience member asked about the parallels between Afghanistan and Vietnam, Holbrooke managed a wan smile. “I was wondering how long we could avoid that question.”
He spoke carefully. As Holbrooke’s contemporaries slipped from power and a new generation took hold, the word “Vietnam” increasingly registered as an unwelcome history lesson. But privately, I had heard him lay out the comparison. In Vietnam, the United States had been defeated by a country adjacent to the conflict, harboring enemy safe havens across a porous border; by our reliance on a corrupt partner government; and by an embrace of a failing counterinsurgency doctrine at the behest of the military establishment. In Afghanistan, he was witnessing echoes of all three dynamics—including yet another administration favoring military voices and missing opportunities for negotiation. “Dick Holbrooke was, of course, a friend of mine,” Henry Kissinger said. “It was a fair comparison,” he observed of the parallels Holbrooke
