Richard Holbrooke and Kofi Annan at the United Nations, October 2000

Tomas Muscionico/Contact Press Images

Richard Holbrooke and Kofi Annan at the United Nations, New York City, October 2000

“Almost great” is George Packer’s measured judgment on the life and character of the American diplomat Richard Holbrooke, who was trying to broker an end to the war in Afghanistan when he died suddenly in 2010. Holbrooke left the war pretty much as he found it, and peace is no closer now, nearly a decade later, but that isn’t what explains the cruel precision of Packer’s judgment. It’s the man. Holbrooke had the serious intent, the energy, the friends, the wit, and even the luck needed to accomplish great things, but he fell short. Packer circles the question of why in his new biography, Our Man: Richard Holbrooke and the End of the American Century, but the force of the man survives the interrogation. Holbrooke spills out in all directions in the manner of Walt Whitman, who waved aside the contradictions that others saw, saying, “I am large, I contain multitudes.”

Holbrooke was not only physically big but had an emphatic personality, could dominate a room, made friends and kept most of them, read widely and greedily, and was a bit overwhelming when he turned his attention on you. It is evident that Packer got the full treatment. They met when Holbrooke had been hovering at the edge of great for decades. As a young Foreign Service officer in Vietnam he knew the war was lost before General William Westmoreland took command of US forces there in 1964. He told early bosses he would be an assistant secretary of state by the age of thirty-five and was (for East Asian and Pacific affairs), and later under President Bill Clinton he served as the American ambassador to Germany and to the United Nations.

The accomplishment cited in the first paragraph of all his obituaries came in the mid-1990s, between his two ambassadorships, when he was an assistant secretary of state for the second time (for European and Canadian affairs). His writ included the warring states of the former Yugoslavia, which were led by intransigent men waging a genocidal war. In the fall of 1995 Holbrooke reasoned and coaxed and threatened these men into signing a peace agreement named for the Ohio city where he achieved what many considered a miracle—the Dayton Accords. That peace has been kept for twenty-three years, and Holbrooke was trying to do the same in Afghanistan in 2009 when Packer published a profile in The New Yorker of the man he already considered a friend.

“What I’m thinking about,” Packer wrote fifteen months later, on the day Holbrooke died,

is not Holbrooke’s role on the world stage, but Richard on the phone for six minutes, or seated across the table, eyebrows lifted and mouth slightly open with barely suppressed mirth. He was the most excellent company. My wife and I were supposed to have dinner with Richard and Kati [Marton, his wife] this Friday. I’ll always wish that evening had come sooner.

It was the warmth, energy, and big presence of Holbrooke that put Packer under his spell, the way a man might fall in love with the city of Rome, all at once and forever. In the first lines of his prologue, Packer puts aside the usual stern mien of a biographer. “Holbrooke?” the writer begins. “Yes, I knew him. I can’t get his voice out of my head.”

But who is this writer? It’s Packer’s book, so it must be him—but the voice is not quite 100 percent Packer’s. This prologue is a risky start. Its writer doesn’t cite anything that Packer in his diligence has not learned for himself, but he knows it the way a guy at the next desk, or an early boss, or a sometime rival for a big job might know it. We may think of this writer—this narrator—as the kind of person, perhaps even a composite of all the people, who told Packer what he knows. Packer is a late arrival; the narrator has been there from the beginning. “Do you mind if we hurry through the early years?” he asks the reader early on. Later he remarks, “I haven’t told you about Holbrooke and women.” It’s the narrator who places Holbrooke in time and explains why Holbrooke is our man—the perfect example of “our feeling that we could do anything…our confidence and energy…our excess and blindness…. That’s the reason to tell you this story. That’s why I can’t get his voice out of my head.”

Holbrooke was not without blemish. He could be abrupt, dismissive, vain, and self-absorbed. Packer is frank about all that but remains in thrall. His Holbrooke is a man who wins, who holds and returns regard. The inevitable question, then, is whether Packer can write a six-hundred-page book about Holbrooke that sees him whole, blinks at nothing, and reaches a judgment we can trust.

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Efforts to portray the life of Richard Holbrooke hinge on its major disappointment—his failure to become secretary of state. How we explain that—not the ambition but the failure—can tell us the sort of man he was. Holbrooke himself traced the first murmur of his ambition to the diplomat Dean Rusk, the father of his best friend while he was growing up in Scarsdale, New York. He spent a lot of time in the Rusk household after the death of his own father in 1957. A year later, at a breakfast gathering of the senior class at Scarsdale High School, the elder Rusk made a suggestion. “When you’re thinking of careers,” he said, “think of the Foreign Service.” Holbrooke remembered that in his junior year at Brown University when President Kennedy chose Rusk to be his secretary of state.

After he wangled a dream job with The New York Times that summer, he told college friends that he knew what he wanted to be: managing editor of the Times or secretary of state. When the Times declined to offer him a job after his graduation in 1962, he took the Foreign Service exam, passed it, and was sworn in a month later. In June 1963, following basic language and area training, he departed for Vietnam just as the long-simmering war was about to spin out of control.

From the moment Holbrooke’s plane touched down in Saigon, his career was swept along by events. The career lasted almost fifty years, but the three Saigon years were the ones that fixed his view of America in the world. Holbrooke arrived when the Kennedy administration was making up its mind that the Saigon government of President Ngo Dinh Diem and his family had to go. The last straw was Diem’s sister-in-law making barbecue jokes about Buddhist monks who had burned themselves alive to protest the war. Holbrooke was too far down the ladder to know anything of Washington’s plotting to get rid of Diem, but something was clearly brewing. “In that strange Saigon atmosphere of ritual suicide and tennis,” Packer writes, “the tension gathered like the saturating air before the afternoon rain.”

Holbrooke’s education began on his second day in-country, when a former military officer, George Melvin, took him north on “Bloody Route 13”—so named for the frequency of attacks on American vehicles. They were heading into the countryside where the official program was to challenge the Hanoi-controlled Vietcong for the allegiance (later invariably referred to as “the hearts and minds”) of rural South Vietnamese. Land reform and rural development were only part of the plan. The unofficial program, Melvin told Holbrooke, also included “certain things that he should never tell anyone,” and “other things that he wouldn’t understand and shouldn’t know or ask about, things on the dark side of the fight that it was wise to keep from higher-ups.” Melvin believed the challenge in Vietnam was political, not a matter of maneuver and firepower. “We have to take the revolution away from the VC,” he said repeatedly.

The rest of Holbrooke’s education, which continued until his departure in the spring of 1966, brought a steadily deepening sense of just how improbable was the plan to take the revolution away from the Vietcong by Ivy Leaguers fresh out of college like Holbrooke, Boston Brahmins who worked too little and drank too much like Ambassador Henry Cabot Lodge Jr., and Hollywood-handsome generals like Westmoreland who thought the Vietcong would be crushed by American firepower. Holbrooke soon grasped the hopeless nature of the task. In a letter to his wife, Litty, from the Mekong Delta, he mocked officials who imagined that “one division of Americans would clean this place up.” He had already learned that “a division of Marines would be bled to death in the swamps and paddies…and never make a dent.” Take that observation, cube it, and you have a good idea of what Holbrooke learned about the limits of American power.

Packer’s hundred pages on the American failure in Vietnam tell the story as forcefully as any hundred pages ever written about the war. The CIA-backed overthrow and murder of Diem and his brother left the Saigon government in tatters, and it never recovered. The war grew steadily bigger but never moved closer to victory. Packer charts Holbrooke’s progress through the four stages of disillusion about the war—learning to be skeptical of official assessments, doubting the tactics, questioning the strategy, and finally admitting that “the United States could never win.” What’s shocking is not how quickly Holbrooke grasped the futility of American efforts, but how readily he concluded there was nothing he could do about it. “The fight sometimes doesn’t even seem worth it,” he wrote in a letter home before his first year was up. “But there is no choice, really, is there?”

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Here the reader rebels. Of course there was a choice, but Holbrooke couldn’t square it with a career in the Foreign Service. This is the line he never crossed. As late as the spring of 1969, he wrote to his friend Anthony Lake, who had just joined President Nixon’s National Security Council, “We have to get out of Vietnam. The war has already spread a poison through our nation.” Holbrooke was willing to tell Lake something they both knew, but he was not willing to wreck his career with futile efforts to tell everybody else. Give his honest opinion on the best way forward, yes; go public with disagreement or even resign, no. That realism, in Packer’s view, was the poison spread by the war. “Vietnam fixed [Democratic doves] with the dreaded label ‘soft,’” he writes; “in government that label could destroy you.” Staying on the safe side of the line was the price Holbrooke paid to keep his professional hopes alive.

Holbrooke’s ambition to be secretary of state was never casual and sank its teeth in deeper as he read history and made powerful friends. He admired secretaries of state like George Marshall (1947–1949) and Dean Acheson (1949–1953) for deserving the job, getting the job, and doing something world-changing with the job—the Marshall Plan, which helped Europe recover from World War II, followed by Acheson’s success in building a grand alliance to defend the West in the early years of the cold war.

In the late 1980s Holbrooke spent four years writing an “as-told-to” memoir for Clark Clifford, who had held a string of high-level jobs close to great events over a twenty-year period—exactly the sort of career Holbrooke wanted for himself. Holbrooke was an able writer, and Counsel to the President is arguably his most revealing work. It builds to the moment in Clifford’s career that gave him a firm place in history—what he did as President Lyndon Johnson’s secretary of defense in 1968.

March 1968, when Clifford took office, was the great either-or moment in modern American history after World War II. General Westmoreland had just requested 200,000 more troops following the countrywide attacks by the Vietcong known as the Tet Offensive. That would have brought the total number of American troops in Vietnam to more than 700,000. The choice was bleak: telling Westmoreland no in an admission of failure or digging in deeper with no end in sight. Johnson was ready to give Westmoreland what he wanted, and at the outset Clifford was ready to go along. But he didn’t. He asked questions, got others involved, forced Johnson to face facts, and pushed him, decisively in Holbrooke’s view, to choose peace talks over endless war. Clifford rose to the moment in 1968, and Holbrooke believed, given a comparable challenge, that he could do the same. Packer tells us that Holbrooke wrote “every damn sentence” of the Clifford memoir, and he infused it with the passion and focus he hoped someone would bring to a similar account of his own life someday.

Richard Holbrooke in South Vietnam, 1960s

Vladimir Lehovich

Richard Holbrooke in South Vietnam, 1960s

Packer strains to isolate the exact thing that set Holbrooke apart and gave him a chance at the greatness Clifford achieved. Holbrooke certainly had ability, and he was given at least two moments of opportunity. The first came in the summer of 1995, when he and three aides headed for Sarajevo to try to end a war. Packer tells us a good deal about these aides, who shared all the dangers of work in a war zone, put in as many hours as Holbrooke, knew as much, and were just as smart. He describes all three as “the kind of career officials who commuted to their offices from the Virginia suburbs in suits and ties…worked long hours and might receive a department award now and then but were unknown outside their circle of colleagues.”

There was no ceiling, but they rose no higher. “If they didn’t make it to the treetops,” Packer observes, “it wasn’t for lack of ability or dedication but want of that demon ambition.” That’s where he comes down: it’s the sheer wanting that brings the most important jobs within reach. This wanting is something colleagues notice early. Packer remarks that in 1972, when Holbrooke’s first marriage broke up, “he had accomplished nothing of importance, yet people began to talk about him as someone destined for great things.”

“But ambition is not a pretty thing up close,” Packer also notes:

It’s wild and crass…. It brings a noticeable smell into the room. It’s a man cajoling a bereaved widow to include him among her late husband’s eulogists, then rearranging name cards so that he can chat up the right dinner guest after the service.

In Packer’s view the “wild and crass” element is what gives ambition its force. To go far, a man or woman has first got to be noticed, then kept in mind and taken into account. “If you cut out the destructive element,” Packer says of Holbrooke, “you would kill the thing that made him almost great.”

In 1995 Holbrooke’s ambition brought him to Bosnia. There to help him were the three able officials Packer has described as unknown outside their own circle of colleagues. They were all middle-aged with wives and two kids each, and they were all in the group with Holbrooke on August 19, 1995, that was forced by fate and politics to take the more dangerous of two routes down into the city of Sarajevo for a round of peace talks. Two military vehicles set out on the steep, winding road over Mount Igman—a Humvee in front with Holbrooke and General Wesley Clark, followed by an armored personnel carrier (APC) with Holbrooke’s three aides.

The disaster that ensued can be recounted in a sentence or two, but Packer devotes twenty pages to his narrative of what happened that day, beginning with his careful introduction and naming of the aides: Robert Frasure, Joseph Kruzel, and Nelson Drew. “It was the most dramatic story of Holbrooke’s life,” he says. He offers two versions of the story: a brief, semiofficial account centering on Holbrooke and Clark; and a second, much longer version in “absurd detail,” which he believes “comes as close to the fleeting truth as we are likely to get.”

In Packer’s first version of the story, the Humvee with Holbrooke and Clark is halted in mid-trip by some French trucks pulled up at the side of the road. A soldier is shouting. Holbrooke and Clark are told that a vehicle has gone off the side of the mountain back up the road. “Then it hit us. They were talking about our armoured personnel carrier!” The rest of that version relates what Holbrooke and Clark did next.

In Packer’s second version of the story, the Humvee sets off down the mountain and the APC follows a moment later. Both are soon going too fast but the Humvee is lucky: it speeds along. The heavier APC is unlucky. It is trying to catch up. As the road winds down the mountain with a cliff wall on one side and a steep drop on the other, the turns are too tight, the road too narrow, patches of gravel make slippery going, and the heavier APC in the rear, trying to keep up with the Humvee, hits a bump, skids to the right, and goes over the edge of the road onto a steep wooded slope, rolling over and over down the mountain as many as thirty or forty times, crashing finally into a big tree a thousand feet down. Some of the occupants are thrown out, some crushed inside. Finding out what happened, seeking and bringing help, and reporting the accident all took time. By day’s end it was known that Frasure, Kruzel, and Drew had all been killed.

Responsibility for the disaster was never established in any official way, but Packer in his second version of the story offers the reader his own take on “the fleeting truth.” The Humvee taking Holbrooke down into Sarajevo started off too fast; the heavier APC, trying to keep up, went off the road. “Holbrooke was the mission leader,” Packer writes, “and he loved speed.”

Packer’s tone in delivering this judgment is restrained; he is not looking for someone to blame but trying to establish what happened. The horror of the accident helps to explain what followed: Holbrooke’s forceful demands to the warring generals in Sarajevo that led a couple of months later to the Dayton Accords. That impressive success put him on President Clinton’s shortlist of plausible candidates to replace Warren Christopher as secretary of state at the beginning of Clinton’s second term. While the president was pondering his choice, Vice President Al Gore urged Holbrooke to fly home from a trip to Bhutan to make his case. Holbrooke imagined, hoped, and may even have allowed himself to believe that his dream was within reach. But Hillary Clinton had something different in mind; she wanted Bill to be the first president to nominate a woman as secretary of state. Other factors played a part, but that was the big one; the job went to Madeleine Albright instead. Holbrooke told his State Department friend Strobe Talbott, “For the first time in my life I feel old.”

Other moments of hope followed. In 2004 Holbrooke was one of John Kerry’s principal foreign policy advisers in his campaign against President George W. Bush, but Packer thinks Kerry had a different candidate in mind for secretary of state. “Joe Biden,” he writes, “had the inside track.”

In 2008 Holbrooke fought hard for Hillary Clinton, but she lost to Barack Obama, and Holbrooke wasn’t on any list of Obama’s, short or long. There was never any warmth between the two men. When Hillary became secretary of state, she engineered a position for Holbrooke as the president’s special representative for Afghanistan and Pakistan. The last two years of Holbrooke’s life were spent trying to square that circle. By the end, Obama was exasperated and close to firing Holbrooke, but the real source of the distance between them had come much earlier, in the aftermath of September 11, when President Bush made up his mind to invade Iraq. Obama was disgusted by the way pushover Democrats had joined the parade. “By the time” Obama was elected, Packer writes, “Iraq was the letter ‘I’ stamped on the foreheads of Democrats like Holbrooke.”

George Packer joined The Atlantic as a staff writer last fall after fifteen years with The New Yorker. His book The Unwinding: An Inner History of the New America won a National Book Award in 2013. The prologue’s writer says he is content to be “a member of the class of lesser beings who aspire to a good life but not a great one,” but that is not Packer speaking. No book could achieve the intensity, completeness, and narrative depth of Our Man without the author’s belief that he had been put on this earth to do it. The strength of the book is its focus on Holbrooke’s character, which Packer pursues much as James Boswell pursued the human truth of Samuel Johnson. The point is not to analyze things—why Yugoslavia flew to pieces, or what Johnson did for the English language with his dictionary. The point is to winkle out and bring to light the whole truth of the man: what he was like in all his contradictions.

Iraq is the issue that explains how Holbrooke fell short, and it provides an illuminating moment when the lives of Holbrooke and Packer unexpectedly veer close. They were both agnostic on the question of Saddam Hussein’s alleged program to develop nuclear weapons, and they both thought he was a cruel, warlike, and unpredictable head of state, but neither seriously argued, and it is probable that neither believed, that the United States had a genuine cause for war or a legal right to invade. That being the case, why did they both support the Bush administration’s decision to invade Iraq in 2003?

Packer’s belief in the war lasted just long enough for him to defend it in his book The Assassins’ Gate: America in Iraq, published two years after the invasion. “The Iraq War was always winnable,” he wrote; “it still is.” But eight months later, in December 2005, he told an interviewer for a San Francisco website that he had changed his mind since he had written that line. “Now,” he said, “I’m quite grim.”

“You were ‘just barely’ pro-war when it started,” the interviewer said.

“It was just hope winning out, by a whisker, over fear,” Packer responded.

That was slicing it pretty thin. Over the next decade Packer reached a far stronger and clearer judgment on the war. “The war was a disaster for Iraq and the US alike,” he wrote in The New Yorker in 2013. “It was conceived in deceit and born in hubris, a historic folly that took the American eye off Al Qaeda and the Taliban, while shattering Iraq into a million bloody pieces.” Packer had to learn that; Holbrooke already knew it when he stood up to be counted for the war in 2003.

Packer does not skirt this moment in Our Man, but his account is brisk and soon concluded; it receives nothing like the intense twenty pages devoted to the APC crash on Mount Igman, much less the hundred-page account of what Holbrooke learned in Vietnam about the limits of military power. In the fall of 2002 Kerry told Holbrooke over dinner that he was thinking of running for president in 2004. It was a tricky moment. President Bush was pressing Congress for authority to attack Iraq, and Kerry, like every other Democrat, was on the spot. “Holbrooke told him point-blank that he had to vote for the resolution if he didn’t want to be seen as weak on national security,” Packer writes. “Holbrooke didn’t add that the same was true for himself in his quest to become Kerry’s secretary of state.”

“It might have been better,” Packer suggests, “to be stupidly, disastrously wrong in a sincerely held belief like some of us.” By this I don’t take Packer to mean practically better—more likely to win plaudits—but better for the soul.

Friends at the time told Holbrooke he was making a mistake to support the war, but he chose the road of realism. To be against that war in that moment, he felt, would mark a man as soft forever. Maybe. But that was a moment when the United States needed bucking up to say no to a rush to war. It was the moment when Holbrooke fell short in Obama’s eyes. Packer cites a whole lifetime of serious work to balance against Holbrooke’s decision to hold his tongue, but it’s hard not to feel that this was the moment that put the almost in almost great.