In the winter of 2009, President Obama was in the Situation Room, polling his national security team about what to do in Afghanistan, where a United States preoccupied by Iraq had allowed the Taliban to regroup, threatening the gains American troops had made in six years of fighting. After going around the conference table soliciting opinions, he turned to a video screen on the far wall that flickered with the image of Richard Holbrooke. Holbrooke, whom Obama had named his special representative for Afghanistan and Pakistan a few weeks earlier, was joining the meeting from Kabul.
A broad-shouldered, barrel-chested man with tousled graying hair and a voice that bristled with portent, Holbrooke was the most storied diplomat of his generation. In a restless career that had spanned nearly fifty years, from Kennedy to Obama, he had accompanied Averell Harriman to Paris for the Vietnam peace talks in 1968; been named the youngest assistant secretary of state for East Asian and Pacific affairs in the history of the State Department, at age thirty-six; served as Bill Clinton’s ambassador to Germany and representative to the United Nations; and brokered the Dayton Accords, ending the cruel civil war in Bosnia. He thought he knew how to talk to presidents.
“Not since Clark Clifford counseled Lyndon Johnson on the Vietnam War has a commander in chief faced such a momentous decision,” Holbrooke intoned, glancing down to read from notes.
“Richard,” Obama interrupted. “Do people really talk like that?”
A chagrined Holbrooke clammed up while the younger aides in the room traded eye-rolling glances. Moments like that made it clear why Richard Holbrooke was going to be a bad fit in the Obama administration. A man of high drama and an acute sense of his place in history, he ruffled feathers in a White House that prided itself on a lack of drama and operated on the principle that the president—and the president alone—makes history. Holbrooke was, in short, not Obama’s kind of guy.
But he was Hillary’s kind of guy. She relished his larger-than-life persona, tolerated his excesses, and defended him against the dart throwers in the White House. She would save his job several times, most dramatically in March 2010, and grieved after his sudden death from a torn aorta nine months later. At his memorial service at the Kennedy Center, Clinton delivered a heartfelt eulogy, reminiscing about the Teletubby-like yellow “sleeping suit” he used to change into on overnight plane trips, and recounting how he once trailed her into a ladies’ room in Pakistan to badger her about something or other. “There was no escaping him,” Clinton said.
It was clear she didn’t want to.
Holbrooke is a rare case in which personal chemistry helps illuminate the deeper differences between Clinton and Obama. The same characteristics that endeared him to Clinton rubbed the president the wrong way. The Henry Luce–American Century worldview he brought to the table was inspiring to Clinton but hopelessly outdated to Obama. He was the embodiment of the generational clash between a young president who came of age after Vietnam and an older secretary of state steeped in the triumphs and tragedies of Democratic foreign policy—many of which bore Holbrooke’s imprint.
It was this Democratic establishment that the upstart senator from Illinois had taken on and beaten in the election. Although Holbrooke was folded into the Obama foreign policy campaign team after Clinton’s defeat—playing a cameo role in an epic cast of three hundred advisers—he was forever marked as a Clinton man. At times, it felt almost like Obama’s aides used him as a proxy for their lingering resentments against Hillary. Certainly, Holbrooke exemplified Clinton’s view of the American role in the world: brash, intrepid, confident that the United States was indispensable to cracking the world’s toughest problems. She admired his wearing-down of the Serbian dictator Slobodan Milosevic at Dayton in 1995, which had produced a major foreign policy achievement for her husband. She liked the way he threw himself at impossible missions, speaking with such passion about helping Afghans to grow crops other than opium poppies, that she dubbed the native New Yorker “Farmer Holbrooke.”
It didn’t hurt that Holbrooke had cultivated her for years. He supported her candidacy in 2008 and was assumed to be a lock for secretary of state in a Hillary Clinton administration. When she ended up at the State Department, she wanted him to be her deputy, a request Obama’s aides denied. They were still bruised by his sharp elbows during the campaign, when he had warned Democratic foreign policy experts who were supporting Obama that they were putting their careers at risk. But Clinton insisted on giving him a major role, and the White House couldn’t argue, given his résumé. With his long interest in Afghanistan, desire to be in the thick of things, and appetite for intractable problems, it was no wonder Holbrooke angled for the Afghanistan and Pakistan portfolio.
“He wanted to be a ‘Great Man,’ so he could change history,” Clinton said in her eulogy, as Obama shifted uncomfortably in his chair behind her onstage. “He was, and he did.”
Holbrooke, however, fatally misread his new president and the political currents in which Obama was operating. He was unable to navigate the shoals in a White House–centric administration. He talked out of both sides of his mouth, appearing to back a troop surge in the Situation Room but privately telling journalists and his friends in New York it would never work. He ran a talented but chronically disorganized shop in the State Department, and he talked constantly with reporters at a time when the White House was determined to control the public narrative. In the end, he fell short of the Olympian goal he set for himself—negotiating a political settlement with the Taliban—though his defenders argue that some in the White House stymied his efforts in a petty attempt to deny him another Dayton.
In the years since his death, the stories of Holbrooke’s humiliations have become the stuff of Foggy Bottom lore. There was the time Jim Jones, the national security adviser, promised he would soon get rid of Holbrooke in a letter to Ambassador Karl Eikenberry in Kabul, and then accidentally copied it to a long list of administration officials. Or the time Holbrooke was kept waiting on a tarmac overseas, with no flight, while junior White House aides emailed each other about whether the Pentagon should approve a military jet to pick him up. Or how he could never get a one-on-one with the president, whom he had asked, rather poignantly, at their first meeting to call him Richard rather than Dick because that’s what his wife wanted.
Five months before his death, Holbrooke, with history on his mind, began recording a diary that offered a window into his anguished frame of mind. The recordings, often made late at night, burn with his ambition to broker a deal with the Taliban, but also with his frustration with a White House that did not value his experience or heed his advice. Obama, he noted, had promised to pursue direct talks with Iran during the campaign, even at the risk of being labeled naïve by Clinton. But when Holbrooke proposed opening a channel to the Iranians to win their support for a political settlement in Afghanistan, Obama’s aides rejected him. “It’s hard to explain that one,” he lamented, calling it a “singular failure of this administration.” Left unsaid was the fact that Holbrooke might have been the wrong salesman for the idea, given the White House’s abiding suspicion of his ambition.
For veterans of the Obama administration, Holbrooke serves as a kind of Rorschach test: he was either the victim of a callow, insular White House, so determined to keep him on the sidelines that they were willing to put their entire Afghan policy at risk; or he was a Clinton-era relic who made enemies, refused to be a team player, and failed to adapt to the age of Obama.
To some, he was both.
“The game he wanted to play was this high-stakes, high-drama game,” said Vikram Singh, a former deputy to Holbrooke who is now vice president at the Center for American Progress, a left-leaning think tank. “It’s not like Richard tried to change himself to fit the no-drama tone and tenor of this administration, which surprised me and did not serve him well.” Derek Chollet, a onetime Holbrooke speechwriter who worked in the Obama White House, said his old boss’s Vietnam references had sent eyes rolling in the Clinton years, too. The difference was that Clinton’s aides viewed him as a talent worth the cost; Obama’s did not. “Rather than seeing Holbrooke as an asset to be used,” he said, “they saw him more as someone who had to be tolerated—and barely tolerated, at that.”
Holbrooke recognized he had a potential ally in Hillary early in her husband’s administration. In March 1995, writing in Foreign Affairs magazine, he had described the American and European response to the Yugoslav civil war as “the greatest collective security failure of the West since the 1930s.” His hyperbolic criticism didn’t sit well with his friends on the NSC staff, whom, after all, he was casting in the role of Hitler’s appeasers. Hillary, though, agreed with him. That summer, when Holbrooke was put in charge of negotiations to end the war in Bosnia and was frustrated by Bill Clinton’s reluctance to take military action, he privately reached out to her for help. Bosnia, he warned, was a “cancer on the presidency”—a message that she wasted no time passing on to Bill. Three years later, when his critics tried to derail his nomination as ambassador to the United Nations, the First Lady stood by him. Holbrooke, she wrote, “had acquired fervent enemies, generally for reasons to his credit. He was ferociously intelligent, strong, often blunt and fearless.”
After the Clintons left the White House and Hillary began her own political ascent, Holbrooke became a constant presence in her life, buttering her up in ways large and small. Each year, he and his wife, Kati Marton, invited her to a holiday dinner at their elegant apartment on Central Park West. One year, Hillary expressed admiration for the work of the Salvation Army; at the dinner the next year, Holbrooke hired a Salvation Army marching band to parade through his dining room, playing Christmas carols. By 2007, Holbrooke was a leading voice on her foreign policy advisory team. That was when he warned fellow Democrats such as Susan Rice and Philip Gordon about the career consequences of signing up with Obama instead of Clinton.
When Obama was elected, he invited Holbrooke to his transition office in Chicago to interview for secretary of state. It was all rather perfunctory: The president-elect had already zeroed in on Clinton for the job. But she had to undergo a vetting process. If that turned up something troublesome enough to disqualify her, Holbrooke would be a credible fallback. The session went badly; Obama seemed immune to his blustering charm. “He took to his first meeting with the president-elect a freight train of negatives—the collected grievances of those who disliked him or with whom he had disagreed in the past,” said Frank Wisner, a diplomat whose friendship with Holbrooke dated back to Vietnam. “He was bigger than life when he came through the door, and he had all these enemies, lots of them. He angered a lot of people because he had this incredible drive and determination.”
Finding a suitable job for Holbrooke was never easy. He had ended up on thin ice in virtually every government post he had held, going back to the Carter administration. Jimmy Carter ordered Zbigniew Brzezinski to cut him out of a meeting with Deng Xiaoping because he was worried that Holbrooke, with his overbearing personality, would upset the delicate negotiations. At the outset of the Clinton administration, he wanted to be ambassador to Japan but was rebuffed by the national security adviser, Anthony Lake, an old colleague with whom he’d long had a complicated relationship. Feeling shut out, a frustrated Holbrooke took off for Southeast Asia and Europe and found himself, improbably, on New Year’s Eve in a freezing hotel room in war-torn Sarajevo.
“If I don’t make my views known to the new team, I will not have done enough to help the desperate people we have just seen,” Holbrooke wrote in his journal. “But if I push my views, I will appear too aggressive. I feel trapped.” He could have written the same words sixteen years later, after Obama’s election left Holbrooke jockeying again for a job in a Democratic administration. But there was one difference: Obama was ready to act in Afghanistan in a way that Bill Clinton had not been in Bosnia.
Though Holbrooke initially regarded the Afghanistan assignment as yet another consolation prize—for not being named deputy secretary of state—he set about turning his new gig into something worthy of his stature. He insisted on being called the special representative for Afghanistan and Pakistan (SRAP), a designation meant to underscore he was the president’s emissary, not some run-of-the-mill special envoy. He coined the phrase “Af-Pak” and was delighted to see it enter the diplomatic lexicon (never mind that some Pakistanis regarded the term “Pak” as an ethnic slur).
Assigned a nondescript warren of offices outside the State Department’s cafeteria that used to house the cashier, Holbrooke quickly assembled a mini-empire of experts from the Pentagon, the CIA, and other agencies. He attracted big names such as Barnett Rubin, a leading scholar on Afghanistan from New York University; Vali Nasr, an Iranian-born academic who had written widely on the Islamic world; and newcomers such as Rina Amiri, an Afghan-born woman who bravely advocated for women’s rights in her native country. He also drew from his New York social world, naming Ronan Farrow as an adviser. Holbrooke had known Farrow since he was fifteen, taking him on as a speechwriter in 2004 as a favor to his celebrity mother, Mia Farrow.
Holbrooke’s empire building antagonized his State Department colleagues, particularly in the Bureau of South and Central Asian Affairs, which he Balkanized to create the SRAP office. In bureaucratic matters, he had all the finesse of a steamroller. When Clinton named Tom Nides, an affable investment banker, as a deputy secretary of state with a portfolio that included the civilian surge into Afghanistan, Holbrooke invited him to lunch at Kinkead’s, a seafood place on Pennsylvania Avenue.
“I just want to make sure you know this,” Holbrooke said, as they unfolded their napkins. “I don’t work for you.”
“Richard, I’m sure you don’t work for me,” Nides replied, even though he clearly outranked him.
In Holbrooke, however, the White House had someone with peerless credentials for the job. As a young diplomat in Vietnam, he had developed firm views about counterinsurgencies, the centerpiece of Obama’s strategy in Afghanistan (he believed they bred a crippling dependency). In the Balkans, he had learned the value of backing up American diplomacy with the threat of NATO bombing raids. As a private citizen, he had traveled to Afghanistan in 2006, where he had met with a jailed Taliban militant as well as with President Hamid Karzai. Holbrooke relished the thin air of the Hindu Kush; he viewed Afghanistan as an even greater challenge than Vietnam. Given his age, then sixty-seven, it would probably be the last big one of his life.
Barney Rubin, who knew more about the Taliban than anyone in the government, argued there was an opening for reconciliation talks, even in early 2009. But nobody was listening to him. Most believed the Taliban were in no mood to negotiate; they were waiting to see what the new president would do. Days after Obama took office, he had asked Bruce Riedel, a savvy former CIA analyst and foreign policy adviser to his campaign, to conduct a quick policy review on Afghanistan. Though Holbrooke was nominally a cochairman of the exercise, he felt shunted aside, especially when he learned that Riedel had presented his recommendations to the president during a flight to Los Angeles on Air Force One (the first of several times that Holbrooke would be left off the presidential plane). Riedel’s forty-four-page report, drawn up in barely two months, called for a “fully resourced counterinsurgency campaign” that would require thousands of American soldiers and civilians to secure the country, train Afghan troops, and help Afghans build the institutions for a stable society. The report flatly rejected the idea of reconciliation, saying the Taliban were “not reconcilable.” It became the template for how the administration dealt with Afghanistan in the years to come.
Holbrooke’s response was to busy himself in other areas that could help the country, like the upcoming Afghan elections, for which he desperately wanted to find a candidate to challenge Karzai. He threw himself into such projects as sending crop specialists from the Agriculture Department to Afghanistan to wean its farmers off poppies. At a meeting in February 2009, while the Riedel report was still being written, Holbrooke began laying out his agrarian vision for the country. Suddenly, Bob Gates cut him off.
“Aw, Richard, nobody in the Department of Agriculture has a clue about how to farm anything,” he said. “That’s not what the Department of Agriculture does. The Department of Agriculture pays people not to farm. If you want farmers, you should go to Texas A&M or someplace like that, where they actually know what they’re talking about.”
If Gates thought Holbrooke was looking for help in the wrong places, his insights about agriculture in Afghanistan were on target. Years earlier, he had written that the Bush administration’s policy of eradicating poppy crops—by burning, spraying, or tilling them under—was counterproductive because it left Afghan farmers penniless, hopeless, and ripe for recruitment by the Taliban. “It wasn’t just a waste of money,” Holbrooke told The Washington Post in early 2009. “This was actually a benefit to the enemy.”
His solution was to set up a system of credit to entice farmers to diversify into legitimate crops such as saffron or pomegranates. Ignoring Gates’s jibe, he pushed the USDA to send fifty-two experts to Afghanistan on one-year assignments, where they offered the farmers advice on irrigation and helped install windmills and open nurseries. He got a kick out of Clinton’s “Farmer Holbrooke” nickname because it was so incongruous for a Manhattan-born urbanite whose prior exposure to agriculture consisted of the organic farm stands he passed on the way to the Hamptons.
Clinton’s patience with Holbrooke was not limitless, however. In one meeting with Pakistani officials, when he wasn’t letting other people speak, she told him to pipe down. Other times, she advised him not to pick fights. At a long session at her house in 2009, she and Jake Sullivan counseled Holbrooke about how to deal with the White House. “She would rein him in, and she would just say, ‘Stop, Richard,’ ” Rosemarie Pauli, Holbrooke’s longtime chief of staff, recalled. “And he would listen to her, because he respected her.” When Holbrooke clashed with Clinton, they tended to make up quickly. On August 9, 2010, he recorded in his diary, they had argued over a strategy memo he was writing for the president on the reconciliation process. Two hours later, Clinton called Holbrooke back to say that the blowup had been a misunderstanding, and that they should start over. “Hillary,” he said, “does not like to apologize or ever say she was wrong, so I understood that to be a gesture.”
In July 2010, Holbrooke brokered an agreement between Pakistan and Afghanistan that would allow Afghan farmers to transport their goods across Pakistan to sell in India. It wasn’t as glamorous as Dayton, but it reinforced Holbrooke’s argument that to stabilize Afghanistan, Pakistan needed to be more cooperative. Shortly after Clinton presided over the handshakes in Islamabad, Holbrooke turned up in the filing center, next to a swimming pool at the American embassy, where the diplomatic press corps were racing to make their deadlines. He had brought along Pakistan’s ambassador to Washington, Husain Haqqani, and a case of warm champagne. As the reporters hunched over their keyboards, he filled plastic cups and delivered a detailed briefing, unfazed that they were too busy to listen.
Clinton and Holbrooke shared a propensity to wear out people with their enthusiasm for wonky issues. But unlike Clinton, who views the world as a series of problems to be solved, one after the other, Holbrooke considered himself a grand strategist. Even as his office was churning out arcane reports on agricultural diversification, he was looking for ways to play a decisive role in Afghanistan’s future. His first foray into the country’s internal affairs would backfire badly.
Holbrooke’s low opinion of Hamid Karzai was no secret when he joined the administration. In a March 2008 op-ed column for The Washington Post, he criticized Karzai for not arresting the fearsome Uzbek warlord Abdul Rashid Dostum after he had attacked and brutalized a rival commander, allegedly with a beer bottle. “Excuses were made,” he wrote, “but none justified his open disregard for justice.” When Karzai was running for another five-year term as president in August 2009, Holbrooke openly rooted for someone to knock him off. He expressed admiration for one of the challengers, Ashraf Ghani, a well-spoken former World Bank official who had been finance minister, even encouraging James Carville to offer him advice. Holbrooke was ridiculed for his infatuation with Ghani, who, though a member of the dominant Pashtun tribe, lacked a political base. (Holbrooke was a better political handicapper than he got credit for: Ghani finally won the presidency in 2014 after surviving a grueling election against his rival, Abdullah Abdullah.)
On August 21, the morning after Afghans had gone to the polls, Holbrooke was in Kabul, warning colleagues that there might have to be a runoff. With so many allegations of vote rigging, Holbrooke expected Karzai would not get the necessary 50 percent of the vote. At a tense lunch later that day, Karzai accused Holbrooke of meddling. “There can’t be a runoff,” Karzai said. “There won’t be a runoff.” In an interview later, Holbrooke acknowledged it was a “frank exchange”—diplomatic code for a shouting match. The damage had been done: His relationship with Karzai was in tatters, and his detractors in the White House now had an opening to undermine him.
Holbrooke was right about the need for a runoff. But when it came time for the United States to have a “come to Jesus” moment with Karzai, the White House chose John Kerry, then the chairman of the Senate Foreign Relations Committee, to be the messenger. Kerry spent hours with Karzai, strolling through the gardens of the presidential palace. He told him about his own frustrations with allegations of voter fraud in Ohio, where he had lost in 2004 to George W. Bush, and Al Gore’s misery four years earlier in Florida. Clinton, barely a year past her own bitter defeat, called Karzai to back up Kerry’s words. Karzai acquiesced to a runoff that November, but after Abdullah pulled out, he was declared the victor.
“John performed brilliantly in every respect,” Clinton told me. “It really came from deep down inside him. He understood the difficult intellectual and psychological struggle that Karzai was going through.” Kerry’s yeoman’s service made him a prime candidate to succeed Clinton as secretary of state in a second term. Holbrooke, who was angling to succeed Clinton himself, had to watch as his job was done by someone else.
When Obama made his first trip as president to Afghanistan in March 2010, three months after ordering the deployment of thirty thousand additional American troops there, his special representative was left off Air Force One. The snub hurt Holbrooke with the status-conscious Afghans and Pakistanis, and it revealed that his problems in the White House went beyond Obama’s campaign veterans. His bigger foes, it turned out, were Jim Jones, the laid-back marine general serving as national security adviser, and Doug Lute, the hardworking Bush administration official whom Obama kept on to run Afghanistan policy in the NSC. “Lute and Jones just blocked him,” a Holbrooke loyalist said. “He never had a chance with them.”
It was characteristic of Holbrooke not to gripe about these indignities, at least in public, or to allow them to slow him down. During this period, he was quietly working on Clinton to back his plan for reconciliation talks with the Taliban. She was frankly skeptical, but Holbrooke arranged a tutorial on the complexities of Afghan society, bringing in his experts to talk to her about the tribal links between the Taliban and Pashtun society. “He would say, ‘Don’t listen to me. Listen to Barney, listen to Vali, listen to Rina,’ ” Vali Nasr recalled. “And she would listen. I’m not saying she was sold, but she would say, ‘Why do you think that? How would that work?’ ”
Holbrooke’s problem was not Clinton. She accepted the argument that there had to be a political solution to the war, though in the early days, she saw more promise in trying to peel off lower-level Taliban fighters than in engaging the high command. His problem was the American generals fighting the war. In early 2009, Clinton brought Holbrooke together with David Petraeus for a get-to-know-you glass of wine at her home, after her own entente with Petraeus. He and Holbrooke began to meet regularly for dinner, and they propagated the narrative of a soldier-diplomat buddy act. It was good copy, and it made sense since a winning war effort would demand a high degree of civilian-military coordination. But behind the scenes, they tangled—a tug-of-war between two supremely ambitious figures that David Axelrod likened to the battle of wits between Sherlock Holmes and Professor Moriarty. Petraeus called Holbrooke his wingman, ostensibly evidence of their tight bond. Holbrooke held his tongue in public, but he bridled at the phrase, complaining to his wife, Kati, “Since when did the diplomat become the general’s wingman?”
The fastidious Petraeus was put off by Holbrooke’s slapdash style. The general once turned up for a meeting in the middle of an interview I was conducting with Holbrooke in early 2010. Rather than kick me out, Holbrooke invited me to stay on for a while, which left Petraeus visibly uncomfortable. As he held forth on the problems in Afghanistan, Holbrooke rested his stocking feet on a low coffee table. Petraeus stared at his wiggling Gold Toes before interrupting him to ask, “Richard, why aren’t you wearing shoes?” Holbrooke, who had bad feet and liked to pad around the office shoeless, waved his hand dismissively, declaring that he was more comfortable without them. Petraeus, glancing down at his own spit-shined shoes, was nonplussed.
Above all, Petraeus did not want Holbrooke’s diplomacy to interfere with his war planning. When I asked the general about the prospects for reconciliation in June 2010, shortly after he had replaced Stan McChrystal as the commander of the International Security Assistance Force, Petraeus made clear it was premature to enter into negotiations with the Taliban while his troops were still fighting to root them out of Afghan villages and towns. “This will not end like the Balkans,” he told me.
“Petraeus is strongly opposing all this,” Holbrooke recorded on August 6. “He says it’s too early and he wants to do it only when he says the time is right, which he says will be next year. Frankly, I just don’t believe him. I think the situation will still be an ambiguous muddle, with elements of progress and elements of retrogression.”
Holbrooke persisted, however. Despite resistance from the Pentagon, the CIA, and some in the White House, he eventually won Obama’s backing to open a secret channel to a Taliban emissary who claimed to represent the one-eyed Taliban leader, Mullah Muhammad Omar. He was an Afghan named Syed Tayyab Agha. Because the contact was so tenuous, Holbrooke opted not to go himself. He sent his deputy Frank Ruggiero and an official from the NSC, Jeff Hayes. To cover his bases with Petraeus, Holbrooke sent the pair to brief the general in Afghanistan after the meeting. “Petraeus was not at all interested,” said an administration official who took part in the session. “His response was, ‘Did you talk about ceasefires? They said, ‘No, that would come at the end of any process.’ And he said, ‘Good. As long as you didn’t talk about ceasefires, then I’ve got no issue with it.’ He was so nervous that the White House was going to blow the whistle and say, ‘Stop your military campaign.’ ”
Petraeus had reason to worry: At the White House, Holbrooke’s ideas on reconciliation were slowly gaining traction. Obama was not especially eager to talk to the Taliban but he was eager to wind down the war, and he recognized one might open the door to the other. Clinton and Bob Gates, though staunch supporters of the military’s counterinsurgency strategy, were attuned to the political pressures facing the president. But Holbrooke’s tensions with Obama’s aides continued to plague him. In this case, the infighting may have gotten in the way of pursuing a path to peace.
At issue was who would lead the talks with the Taliban. Holbrooke and Clinton assumed that, naturally, it would be the hero of Dayton. But Jones and Lute could not bear the thought of Holbrooke reenacting his Balkans triumph in Afghanistan. Lute was resentful of his high-handedness. He thought the United States, as a combatant, should not be at the table cutting a deal between the Taliban and the Afghan government. And anyway, Karzai, who had distrusted Holbrooke since the election, would never abide him as a mediator. So Lute came up with the idea of giving the assignment to Lakhdar Brahimi, a wizened Algerian diplomat then serving as the United Nations representative in Kabul. “Brahimi is a distinguished UN diplomat who knew Afghanistan and had a trusting relationship with Karzai,” Lute told me. “The UN had convening power among key players that the U.S. did not.”
Clinton had gotten wind of this scheme in advance and told Obama she opposed bringing in the UN envoy. When Lute and a colleague presented it to the president, they got a withering response. “This is screwed up,” the president said, according to someone who was in the room. “You guys come in here knowing that Secretary Clinton opposes this, and ask me to do an end-run around her?” (Lute said he did not recall the meeting with Obama and would not have tried to circumvent Clinton.)
It was not the first time Clinton had saved Holbrooke’s skin. A few months earlier, while Clinton was on a trip to Russia, General Jones had summoned Holbrooke to his corner office in the West Wing and told him he should plan his departure from the administration. A stunned Holbrooke, thinking he had just been fired, retreated to his rented house in Georgetown to consider his options. Tom Donilon, an old friend then serving as Jones’s deputy, advised him to do nothing. But Rosemarie Pauli—whom he had asked to come to the house, along with his press assistant, Ashley Bommer—urged him to appeal to the secretary of state. Holbrooke’s first call was to Jake Sullivan, whom he woke in a Moscow hotel room in the middle of the night.
A few hours later, Sullivan briefed Clinton, and another campaign to save Holbrooke began. She had asked Strobe Talbott, a mutual friend of hers and Holbrooke’s, to be part of an informal support group for him. The day after she returned from Russia, Talbott emailed her about a lunch he’d had with Donilon that was dominated by White House complaints about Holbrooke. “It sounded quite ominous re his immediate boss, and not great re the ultimate one,” he wrote, referring to Jones and Obama. Sullivan put together the equivalent of a legal brief for Clinton, itemizing the achievements of the SRAP staff and explaining the distinctive nature of Holbrooke’s leadership. Armed with that, she requested a meeting with the president.
“Jim Jones can’t fire Richard Holbrooke,” Clinton told Obama, according to two people who were briefed on their exchange. “I can. You can. If you want to fire him, it’s certainly your prerogative, but you’ll be doing it over the objections of your secretary of state.” Obama countermanded Jones, and Holbrooke lived to fight another day.
Nothing better exemplified Holbrooke’s troubles with the White House than the September 2009 issue of The New Yorker. It contained a long, admiring profile of him under the headline “The Last Mission.” While it did not trigger his dismissal, as would the explosive profile of Stan McChrystal in Rolling Stone a year later, it shared some of the same features: an exotic backdrop and a colorful narrative, based on unusual access to a swashbuckling hero who was not named Barack Obama. As soon as the magazine hit newsstands, Denis McDonough called Holbrooke on the carpet. He was particularly incensed that Holbrooke had allowed the writer, George Packer, to sit in on a meeting between him and Karzai. The State Department spokesman, P. J. Crowley, gave Clinton a heads-up on the article via Cheryl Mills. “Richard strayed shall we say from discussion of our strategy,” he emailed. Holbrooke’s cultivation of reporters had long been a sore spot with Obama’s aides, who tried to keep tight control over such contacts; this piece made them neuralgic.
It is true that Holbrooke was catnip to journalists, in part because they recognized him as a kindred spirit. A onetime news clerk at The New York Times, editor of Foreign Policy magazine, and columnist at The Washington Post, Holbrooke had moonlighted as a writer even as he established himself as a top-shelf diplomat. He offered reporters unsolicited critiques of their works, and his obsession with their coverage was comical. Dozing on a flight out of Afghanistan one night in 2010, I suddenly felt a silent presence over my left shoulder; it was Holbrooke peering at the half-written article on my open laptop. When I snapped the computer shut, he shrugged his shoulders and started a conversation about something else.
For all his palaver with journalists, Holbrooke was a better dispenser of analysis than scoops. When I asked him in the fall of 2010 whether the United States was ready to talk to the Taliban, he replied that it was an “over-the-horizon” issue. Not that far over the horizon, in reality: He was about to send his deputy to the first secret meeting, in a village outside Munich, Germany, with the Taliban emissary, whom he had dubbed A-Rod after the not-yet-disgraced New York Yankees slugger. Holbrooke said little about his alienation from the White House and never publicly criticized the president.
In December 2009, Obama traveled to West Point to announce the troop surge. Holbrooke, who told Clinton privately that he had deep doubts about the plan, was, as usual, not invited to go with him. So, instead, he flew to Brussels, where he convened a meeting of Af-Pak representatives from other countries and delivered a briefing on Obama’s decision. It all looked very coordinated but it was largely a way for Holbrooke to save face, to paper over being sidelined back home. However brave a front he put up, he privately despaired over his lack of entrée to the Oval Office.
Holbrooke’s audio diary became an outlet for his frustration with the White House. He was wounded when Clinton and Donilon told him that the president wanted him to drop his constant references to Vietnam. “I was very struck by this,” Holbrooke said, “since I thought there were obviously relevant issues.” He mixed jabs at Donilon (“Tom’s strengths are political and public affairs; he doesn’t have a strategic sense”) and Rahm Emanuel (“He’s smart, he’s quick, but he’s just not very nice, at least not to me”) with tidbits about his own Gatsby-like social life (an eightieth-birthday party for George Soros, held under a tent for five hundred at a Hamptons horse farm). But the recordings also captured the unabashed patriot and incurable romantic in Holbrooke. He talked about seeing a revival of South Pacific at Lincoln Center in August 2010 and being struck by the America of Rodgers and Hammerstein, a country at the zenith of its power after World War II. “The contrast with today,” he said, choking up. “It was very powerful, and I just kept thinking of where we were today, our nation, our lack of confidence in our own ability to lead, compared to where we are in 1949, when it came out, evoking an era only five to seven years earlier, when we had gone to the most distant corners of the globe and saved civilization.”
By that fall, Holbrooke’s friends were advising him to leave on his own terms. He told them to mind their own business, but they were beginning to worry about his health. Though he was a sturdy man, his punishing work and travel were catching up with him. At lunch with Frank Wisner at the Metropolitan Club in New York, the two were tucking into their customary menu of congressional navy bean soup and two-dozen Cherrystone clams. Holbrooke, who ate with the same brio he did everything else, nicked the tip of his nose with the edge of a clamshell, and blood spurted out. “We had to get napkins to staunch the flow, and I said, ‘What the hell’s wrong with you?’ ” Wisner recalled. It was then that he learned his friend was taking heavy doses of Coumadin, a blood-thinning drug prescribed to people with heart disease.
A few days after the secret Taliban meeting in Germany—the first step in his gambit to negotiate a settlement with the Taliban—Holbrooke suffered the tear in his aorta that would kill him. The previous evening, he had dined at a Georgetown restaurant, 1789, with Michael Abramowitz, a former Washington Post reporter and the son of another renowned American diplomat, Morton Abramowitz. He recalled Holbrooke being subdued and tired but engaged. They chatted about trends in journalism (mostly negative, in Holbrooke’s view) and geopolitics (he saw the Caucasus as the next major flashpoint).
The next morning, Holbrooke dropped in on David Axelrod at the White House to plead yet again for a one-on-one with the president. Axelrod told him he would see what he could do. His assistant, worried about Holbrooke’s flushed appearance, offered him a glass of water. Then he went to Clinton’s office, where, during a session with her and Jake Sullivan, his face abruptly turned dark red and he was suffused by pain. Holbrooke was rushed to George Washington University Hospital, where he underwent twenty-one hours of emergency surgery and became the focus of a worldwide vigil. Hamid Karzai and President Asif Ali Zardari of Pakistan both called Kati Marton on her cellphone to offer their best wishes. In a twist Holbrooke would have appreciated, his heart surgeon, Farzad Najam, was from Pakistan.
Even in physical agony, Holbrooke’s combination of charm and intensity didn’t leave him. Told by the attending physician, Jehan El-Bayoumi, that he needed to relax, he said, “You have to promise me that you’re going to end the war in Afghanistan.” OK, she said, and then she asked him to close his eyes and imagine being on a beach. “I don’t like beaches,” he said. When she asked him what he wanted to imagine, Holbrooke replied, “a beautiful woman.” Suddenly, his eyes opened.
“You!” he exclaimed.
It is hard to know if things would have gone differently in Afghanistan had Richard Holbrooke not died on December 13, 2010. Some in the administration argue that Lute’s attempts to block Holbrooke from talking to the Taliban, by promoting a UN envoy in his place, paralyzed the process at a critical juncture. If the White House had simply made Holbrooke the negotiator, a former NSC official said, “the talks with the Taliban would have started earlier and progressed further.” But Obama was determined from day one to withdraw American soldiers from Afghanistan. By telegraphing his intentions so early and often, he may have foreclosed the possibility of any meaningful negotiation with the Taliban. They knew they could wait out the Americans.
The bittersweet postscript to Holbrooke’s last mission is that two months after he died, Clinton finally opened the door to reconciliation. In a speech at the Asia Society dedicated to her old friend, Clinton challenged the Taliban: “Break ties with al-Qaeda, give up your arms, and abide by the Afghan constitution, and you can rejoin Afghan society.” It was a familiar demand, but there was a twist: She now was saying that the Taliban could meet these criteria as a result of negotiations, not as a precondition for them. That made diplomacy possible in a way it had not been before.
With the door to talks open, the White House explored various channels, some rather far-fetched. One involved negotiating with the Taliban through an intermediary, Hamid Gul, a retired Pakistani general who had been the head of Pakistan’s powerful spy agency, the Inter-Services Intelligence Agency, or ISI, which had long had ties with the Taliban. On the American side, the emissary was to be Bruce Riedel, author of the first Afghan review. Like many of these schemes, the idea went nowhere.
Holbrooke’s successor, Marc Grossman, plunged into a delicate negotiation with the Taliban and Karzai, who was deeply suspicious of American efforts to broker a settlement without him. Grossman was a career diplomat as low-key as Holbrooke was larger-than-life, but he had one advantage: no baggage with the White House. In one of his first meetings, he revived Holbrooke’s idea of reaching out to Iran for help on Afghanistan. “Everyone said, ‘Sure, go ahead,’ ” a senior official recalled. Amazed at meeting so little resistance, Grossman asked his State Department colleagues to explain. “The White House didn’t allow Dick to do that,” one told him, “because they thought the only reason Dick wanted to talk to the Iranians was to be the one to talk to the Iranians.”
Grossman’s overture to Iran was unrequited; his diplomacy with the Taliban was doomed by Karzai’s suspicions and a chain of clumsy miscommunications over a political office the Taliban opened in Qatar. The militants hung a sign and raised a flag over the building, drawing fierce protests from Karzai, who said they were presenting themselves as a government-in-exile. When the United States finally achieved a diplomatic breakthrough with Iran five years later, the credit went to John Kerry, and, ultimately, to Obama. In the end, the only deal ever struck with the Taliban was a prisoner swap in which five of their fighters held in Guantánamo Bay, Cuba, were exchanged for Sergeant Bowe Bergdahl, an American soldier who walked off his base in Afghanistan and was captured and held by the Taliban for nearly five years. Given the army’s later charges that Bergdahl was a deserter, it was not much of a deal—a threadbare alternative to the grand bargain Holbrooke had in mind, not to mention a lingering political headache for the president.
“Richard was a big-picture guy in a small-picture administration,” said Husain Haqqani, who met him for breakfast at the Four Seasons Hotel in Georgetown the day before he became ill and recalled Holbrooke venting frustration at his inability to build trust with Pakistan’s military commanders. “How could you have a special representative who was not special, and not representative of the president?”
A few weeks after Holbrooke’s death, his widow, Kati Marton, was invited to lunch at the White House mess by Samantha Power, who had been one of his acolytes. She ran into Denis McDonough, who expressed his sympathies and said, “Kati, if there’s anything we can do, let us know.”
“Only because Samantha was next to me, did I not say, ‘I wish you had made that offer to Richard when he was alive,’ ” she told me. “That the president couldn’t take ten minutes because Richard wasn’t cool enough, wasn’t a temperamental soul mate? That speaks to a very specific lacuna in the president’s character—that he’s not ultimately comfortable beyond his very narrow zone.”
Marton, a writer and former ABC News correspondent, waged a campaign to bury her husband at Arlington National Cemetery, even though he did not meet the requirement of having been an active or retired member of the military. She asked Clinton and the former chairman of the Joint Chiefs of Staff Mike Mullen to send letters on his behalf. Holbrooke’s “public service was inextricably intertwined with our military,” Clinton wrote on September 8, 2011, “and, more than once, Richard found himself on the front lines, the living embodiment of ‘one mission, one team.’ ” Six weeks later, the army secretary, John McHugh, wrote back to Marton to say, “Ambassador Holbrooke, unfortunately, is not eligible to be laid to rest at Arlington.” Marton thinks the White House could have intervened to waive the rule.
Holbrooke’s eldest son, David, made a nuanced HBO documentary about his father, The Diplomat. His research for the film left him with a more philosophical view of Holbrooke’s ordeal. Looking back, he says, his father’s generational disconnect with Obama could have been foretold in an encounter his son had with the president on the day Holbrooke was appointed. Shaking Obama’s hand, David, who was forty-three at the time and plays respectable, middle-aged basketball, told him, “Any time you want to ball up, let me know.” Obama laughed and asked him what kind of game he had; David, who is six foot six, replied that he resembled Horace Grant, the solid, if unspectacular, power forward who played for the 1990s Chicago Bulls. “My dad would probably have said Bob Cousy,” David said, referring to the Boston Celtics superstar whose heyday was in the fifties and sixties.
Clinton has said little in public about Holbrooke’s travails. Privately, friends say, she is still offended by the way the White House treated her friend. In her memoir, she did not bother to quote from Obama’s eulogy, in which he placed his envoy in a line of diplomatic giants from Dean Acheson to Clark Clifford. Much has been made of the cringeworthy dynamics at his memorial service: the pinched president, praising the man he never had time for; the emotional secretary of state, mourning the man who didn’t leave her alone. Perhaps the strangest moment, missed by all but the lip-readers in the front row, came when one of Holbrooke’s oldest friends, Leslie Gelb, described him as being “like Odysseus”—“a leader of men, and women, and interns.” The audience cracked up at the word “interns,” but Bill Clinton, who was sitting onstage where the acoustics were poor, didn’t catch it.
He leaned over to Hillary for clarification.
“Interns,” she mouthed, her eyes narrowing. “He said ‘interns.’ ”
Obama’s remarks were faultlessly dignified but utterly impersonal. Only once, for a moment, did his mask drop. “So full of life,” he said of Holbrooke’s over-the-top energy, “he was a man both confident in himself and curious about others.” At the word “confident,” a smile flashed across Obama’s face and he cast a knowing glance at the audience. Though he placed Holbrooke in the pantheon of Democratic statesmen, it was precisely this status that made Obama and his aides suspicious of him. They were determined to break free of that cohort and its well-worn nostrums—nostrums to which Clinton wholeheartedly subscribed. In the process, however, they failed to benefit from the decades of experience he brought with him. “I can understand the desire to think more creatively and to change things and to think there’s an old guard,” said Dan Feldman, a Holbrooke deputy who later served as the special envoy, “but not at the expense of losing institutional memory and history.”
In retrospect, the president’s aides admitted, they could have handled some things differently. “If Obama having a one-hour lunch with Holbrooke would have made him feel that much better, we could have done that,” Ben Rhodes told me. The White House also could have made it clearer that when it forbade him from giving television interviews, it was because, in the throes of the Great Recession, the administration wanted only economic officials on television. Afghanistan was a distraction for a domestically focused president. That speaks to a larger truth about Holbrooke: His job title never matched his self-image.
“I don’t think the president was aware that there was so much drama surrounding Richard Holbrooke,” Rhodes said, in a comment that would have cut his special representative to the quick.
After Holbrooke’s death, the drama was hard for Obama to avoid. In the flood of elegies to him, a narrative took hold: His relentless turf battles with the White House had worsened his health problems; the rigors of his last mission somehow had precipitated his death. The president began to take it personally. At a White House meeting on Afghanistan a few weeks later, said a person who was there, Obama complained, “I’m sick of people writing about how I killed Richard Holbrooke.”