senior Bush administration officials said they seldom, if ever, confronted Pakistan about the support for terrorists, for fear of jeopardizing the counterterrorism alliance. Hayden recalled only one such direct conversation, late in the administration, in which Musharraf “fobbed it off on retired ISI officers. You know, the ones who supported the ‘mooj’ during the Soviet War.” The US had helped create Pakistan’s state sponsorship of militant Islam in that era, and now it couldn’t put the genie back in the bottle. If it wanted to, Hayden argued, that would take more than the narrow confines of intelligence and military cooperation. “Look, I mean, the director of the CIA is not going to cause the government of Pakistan to change course based upon a conversation he has in either Washington or Islamabad,” he said. “That requires a whole government effort of long-term … and really powerful sanctions that I saw no evidence that we were prepared to make.” He was describing the urgent need for a larger diplomatic effort that would never take place.
The result of Pakistan’s double-dealing, and the United States’ relative tolerance of it, was a slide into violent turmoil on the Afghan side of the border, with the Taliban steadily resurging over the course of the Bush administration. American and NATO operations offered periodic pushback, but the supply of fighters always replenished from the safe havens in Pakistan. Over the course of Bush’s second term, the insurgency gained strength, staging devastating attacks, sometimes with the Pakistani military providing cover from across the border, firing on American and Afghan soldiers. The Taliban’s gains allowed them to establish a parallel government in the country’s south and then east—complete with governors and judges. By the beginning of the Obama administration, America was losing.
AS AFGHANISTAN AND PAKISTAN unraveled, Richard Holbrooke was still chasing the role he felt he was born to play: secretary of state. I first met him as he came close yet again in 2004, throwing his weight behind John Kerry’s failed bid for the presidency. Holbrooke was a private citizen then, working as an investment banker again, but still a fixture at United Nations and charity functions. I was working with UNICEF, in New York and several conflict zones. In Sudan, I began cranking out Wall Street Journal and International Herald Tribune columns about a gathering ethnic cleansing campaign there. For years, Holbrooke was religious about sending appraisals of my stories: “Ronan, this is a splendid, vivid piece … You should try to get lift-off on this issue with State and the UN. I’ll send it around.” Or, just as often: “Next time, put a bit more emphasis on solutions so that it comes across as more than an anti-UN rant.”
He took correspondence seriously. In that 2010 State Department speech marking the release of the Vietnam documents, he lamented that “in all likelihood, the volumes being released now will never be matched again … with emails and video teleconferences, documentation just isn’t what it used to be.” He was, by the time I knew him, a practitioner of dying arts. That I was far too young for any of it—a teenager, when I interned for him during his time advising the Kerry campaign—never seemed to faze him. It made sense: he himself had perfected the art of being too young and outspoken for his station. He let me in, and I was green enough to think nothing of it.
Holbrooke was on the outside then, a role that would become familiar in the following years. So it was on January 19, 2009, the night before President Barack Obama’s inauguration and the prime moment for the preinaugural parties that send DC elites into a frenzy of invitation chasing every four years. One such party, hosted by Republican socialite Buffy Cafritz and her husband Bill, had been a venue for bipartisan schmoozing since the 1980s. Most years, it drew 250 or 300 guests. This year, more than 500 packed the ballroom of The Fairfax at Embassy Row, humming with excitement. Movie star jostled politician jostled reporter. They huddled, cocktails in hand, necks craning for marquee names from the new administration. Change was in the air, and everyone wanted to be a part of it.
You can feel the energy of a crowd of political operators change when someone worth currying favor with walks in. When Bill and Hillary Clinton walked in that night—she, defeated on the campaign trail but lifted by her nomination as Barack Obama’s new secretary of state—the dimly lit ballroom practically tilted. Hillary Clinton smiled a wide, frozen smile and nodded her way through the crush. Huma Abedin, Clinton’s longtime body woman, trailed behind, thumbs pounding on her BlackBerry.
Richard Holbrooke had been studying the crowd with undisguised intensity, eyes darting across the sea of faces as he half paid attention to our conversation. He was standing at the outskirts of the ballroom in an ill-fitting charcoal suit and a purple and white tie. At sixty-seven, he was overweight and graying; a universe and a generation apart from the lanky Foreign Service officer smiling from behind horn-rimmed glasses in photos from the Mekong Delta. But the smirk and the piercing eyes were the same.
We caught up briefly. But Holbrooke’s focus never left the crowd. He was “on.” This was work. When Clinton entered the scene, he departed with a clipped “We’ll talk later,” and strode over to her, fast enough to attract a few sideways glances. He and Clinton had been close since her husband’s presidency, when Holbrooke was at times a mentor during her early years on the international stage. During the coming administration, she would prove to be his staunchest defender. But he never seemed on sure footing in those years, even with her. Every moment of precious face time counted. “One could not be with him for even the briefest period without knowing how badly he wanted to succeed,” the war reporter David Halberstam wrote after becoming close with Holbrooke in Vietnam. That night at the Fairfax was Exhibit A.
IN BACKING HILLARY CLINTON, Holbrooke had, once again, bet on the wrong horse. But he was scrappy as ever, and the moment Clinton lost the 2008 primary, he began a campaign to break into an Obama administration to which he was very much an outsider. He worked the phones, calling anyone he could think of until, finally, friends told him to rein it in. For a time, he held a record for having appeared more often than anyone else on the PBS interview show hosted by Charlie Rose. In an August 2008 appearance, he tried, frantically, to pivot toward Obama.
“I supported Senator Clinton, based on an old and close personal relationship and long-standing commitments. But I—I’ve read Senator Obama’s positions extremely carefully … and there was no major position he took which I would disagree on …”
“He also brought together a group of thirteen foreign policy people … And a lot of people noted that your name—your presence was not there,” Rose fired back. Holbrooke never had much of a poker face, and looked, for a moment, almost despairing. “And they were disappointed, frankly,” Rose went on, “because they think you are one of the principal spokespeople for foreign policy on the Democratic side of the aisle, because of your wide experience and your—”
“—My frequent appearances on your program.” He laughed a little too hard.
“Your frequent appearances on this program. Why weren’t you there?”
“I think I was doing a program with you.”
“Be candid with me. Tell me why you weren’t there and what was the story?”
Holbrooke glanced to the side then said, in a tone that suggested he’d rather douse himself in gasoline and self-immolate on that oak table than admit what he said next: “I wasn’t there because I wasn’t invited.” To which he added quickly: “I don’t have any problem. They can have anyone they want at a meeting. Actually, I was out of the city on that day