BOSTON — U.S. President Barack Obama’s special representative to Afghanistan and Pakistan, Richard Holbrooke, who died Monday, held deep doubts about the war he was publicly defending — thoughts he is reported to have expressed on his death bed.

In the last conversation I had with him, just before a recent trip to Afghanistan, he expressed some of his concerns. Although upbeat in public, in private he was not at all sure that Obama’s surge, or Gen. David Petraeus’ counterinsurgency strategy, were going to work.

“The war won’t end with a military victory,” he said. “We all know that. Even Petraeus admits that. But there is no agreement on how it will end.

“In Vietnam, in Serbia, you knew which phone to pick up to end the war,” he said. “But given the fractured nature of the Taliban, we don’t have a phone number. That is unique in American history.” There are “at least five groups” affiliated with the Taliban — "even more when you look closely,” he said. “Are we talking about fragmenting the enemy and making deals? Or are we talking about a grand bargain to include them all?”

(Read about Holbrooke's legacy in Afghanistan and Pakistan.)

Holbrooke said one might get the “tribes to come in from the cold.” That could be done if you said to them, stop fighting us and we will let you control your valley. “That’s what Petraeus did in Anbar [Iraq.] He even took people who were murdering Americans and made very smart deals with them. History will tell whether its permanent,” but it worked well in the short run, because it "allowed Obama’s withdrawal policy to succeed.” But that was no guarantee it would end the war in Afghanistan.

Petraeus and Obama fundamentally disagree about how long America should be prepared to stay on and fight in Afghanistan, Holbrooke said, but the irony is that “now Petraeus will decide the fate of the Obama administration.” After having fired two generals, Obama cannot afford to lose Petraeus lest he seem incapable of working with the military.

Holbrooke, alone in the Obama team, was old enough to have held a responsible job in Vietnam, and the experience haunts him. He kept bringing up the lessons of Vietnam within the Obama administration, which the president and his team did not always appreciate. But although he might question tactics, Holbrooke always felt that Afghanistan was strategically important — far more than Vietnam.

The Afghan people did not want the Taliban back, he said, “but the international community will not give us time if the Taliban keep surging, and they have matched Petraeus surge for surge.”

Holbrooke complained that the military, until the arrival of Gen. William Caldwell a year ago, had failed in its task of building up an Afghan army and police force. Caldwell had turned things around, he said, but we were nine years too late out of the box. He saw a “tremendous debate” coming between Obama, who wanted “steep and deep” troop withdrawals, and Petraeus who wanted withdrawals to be “small and shallow.”

Holbrooke’s Vietnam experience reminded him that the overthrow of South Vietnam’s Ngo Dinh Diem simply led to a downward spiral, and he made it clear he would never be a party to a coup against Hamid Karzai.

But he called Karzai “a dark and difficult man” subject to wild mood changes. His own relationship with the Afghan president had been fractious, but he expressed fury against whoever it was in the White House who leaked the cable of Ambassador Karl Eikenberry saying Karzai was an inadequate partner and a slender reed on which to base our strategy. This simply infuriated Karzai for no good reason. The White House had leaked the cable, Holbrooke thought, to counter the military’s leak of Gen. Stanley McChrystal saying we had to have more and more troops.

Always a complicated man, Holbrooke, whom I had known for 40 years, sometimes gave the impression that his talents were put too much in the service of his ambition.

That impression was not always accurate. He could be humorous, kind to a fault, but never reluctant to state his views. At dinner parties he would erupt at someone he disagreed with, sometimes shouting down an errant guest. But on other occasions he could be spellbinding with his lucidity, vision and grasp of events.

When he was first being considered for his last government post, U.S. Vice President Joe Biden said, "He’s the most egotistical bastard I have ever met.” This remark was widely quoted when Bob Woodward reported it. But often left out was Biden’s follow-up: “… he may be the right guy for the job.”

Woodward wrote in his book “Obama’s Wars,” that “though absorbed with being a hero, Holbrooke was so committed to succeeding that he would focus his extraordinary talent, energy and ego on the assignment and might just pull it off.”

Ambassador to the U.N., to Germany, under secretary of state for Asia and for Europe, Peace Corps director in Morocco, Holbrooke came of age professionally in Vietnam. His finest hour was the Bosnian peace accords, which he achieved by banging reluctant Balkan heads together. Whether his tactics would work with Pakistanis and Afghans was always a question I had.

Despite Holbrooke’s brilliance and diplomatic achievements, the one post he really wanted, secretary of state, always alluded him. Al Gore, as vice president, lobbied for Holbrooke, but President Bill Clinton chose Madeleine Albright.

Before the 2000 election, Gore told me that Holbrooke would be his choice for State. In 2008 he came out for Hillary Clinton, and there was every indication she might also have picked him for the post. But, like their presidencies, it was never to be.

Related Stories