It seemed almost foreordained that Richard Holbrooke would have a difficult, unhappy stint in the Obama administration. He had the wrong history, personality, and operating style to fit in with the Obama inner circle, much as Holbrooke struggled in his own fashion to do so. He was of the wrong generation, serving at the wrong time.
Holbrooke was a living symbol of the foreign-policy establishment against which the Obama team had campaigned. He had been serving Democratic presidents since the 1960s. The Obamians saw themselves as insurgents; Holbrooke had always tied himself to power, to worldly, prosperous Democrats like Averell and Pamela Harriman, Clark Clifford and the Clintons.*
Holbrooke would almost certainly have been secretary of state if Hillary Clinton had won the presidency. He might also have landed that job if Al Gore had won in 2000 or if John Kerry had beaten George Bush in 2004. After Obama appointed Clinton as secretary, she hoped to name Holbrooke her deputy, but Obama gave that job to Jim Steinberg, who had been a leading candidate for national security adviser.
Instead, in 2009, eager to return to government, Holbrooke took the lesser job he was offered, as the president’s special representative for Afghanistan and Pakistan, or “Af-Pak,” as he soon called it. He found himself, for the third time in his career, working within but not quite at the top of a Democratic administration, obliged to serve under those who seemed to know less history (and fewer powerful people) than he did. He was working for a secretary of state whom he had tutored in foreign policy and for a president who had been seven years old in 1968, when Holbrooke began working for Harriman at the Paris peace talks on Vietnam.
The rationale for giving Holbrooke the “Af-Pak” job was that while his outsize personality might create problems in Washington, he was especially good at fixing specific, hands-on problems overseas. Together, the wars against the Taliban in Afghanistan and against al-Qaida in Pakistan were among the highest priorities for the new administration. The Af-Pak assignment was meant to be a follow-on to the work Holbrooke had done in the Balkans during the Clinton administration. There, Holbrooke had managed to push, shove, and cadge the leaders of Bosnia, Serbia, and Croatia into accepting the Dayton peace settlement. His aggressive operating style had served him well in dealing with Serbia’s Slobodan Milosevic. a tough leader who needed to hear some blunt language and threats along with the standard diplomatic niceties.
The problem was that Hamid Karzai, the president of Afghanistan, did not stand in the same position as Milosevic in the 1990s. The Serbian leader was an adversary; Karzai was a shaky ally. Holbrooke could threaten Milosevic that if he balked, he might confront awesome American military power (and, indeed, the United States and its NATO allies eventually did bomb Belgrade). Holbrooke couldn’t similarly threaten Karzai with the bombing of Kabul. Ultimately, the Obama administration needed the help and cooperation of Karzai’s government. The applicable historical precedent for dealing with Karzai wasn’t Milosevic at all. Rather, the closer comparison was those leaders aligned with the United States in the Cold War who proved increasingly unpopular at home and obstreperous in dealing with Washington. Both Nguyen Van Thieu in South Vietnam and Ferdinand Marcos in the Philippines fit this description well.
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Holbrooke quickly ran into even more serious problems in Washington. In the fall of 2009, the underlying tension and mistrust between Holbrooke and the Obama White House boiled to the surface. The precipitating factor was a profile of Holbrooke in The New Yorker. Written by George Packer, the article was entitled “The Last Mission.” It told the story of Holbrooke’s career from his early days serving in the Vietnam War to his new job in the midst of the war in Afghanistan. There were reflections by Holbrooke on the lessons from Vietnam for Afghanistan, comparisons and contrasts between the two countries, and pictures of Holbrooke in both Vietnam and Afghanistan—all of them introduced by a glossy portrait photograph of Holbrooke, covering one and a third pages.
Denis McDonough, the deputy national security adviser, who rarely said or did anything without the president’s approval, summoned Holbrooke to the White House for a strained conversation. Holbrooke and McDonough were probably the two most press-conscious officials in the entire administration: Neither was modest about calling reporters to try to shape a story in advance or to complain about something after it appeared. But the similarities stopped there. Holbrooke called the press on matters involving himself or his own causes and issues; McDonough was a staff man who pushed, equally aggressively, on behalf of his boss Obama.
At their meeting, McDonough dressed down Holbrooke, pointing his finger for emphasis. He told Holbrooke that the president was unhappy about the magazine article, which had drawn attention to Holbrooke, not the administration, and portrayed Afghanistan in a way that centered on Holbrooke’s own story. The White House wanted to set the messages and images of the administration, and not have various individual actors send out a cacophony of ideas.
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On Sunday, Dec. 5, 2010, Richard Holbrooke played tennis on Long Island with Bill Drozdiak, the president of the American Council on Germany, a former foreign correspondent who became friendly with Holbrooke when both were living in Europe. They played for about an hour. Drozdiak thought Holbrooke seemed unusually pale, pudgy and out of shape, as if he’d been working too hard.