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 and I couldn’t have gone anyway.”
Rose asked if he’d spoken to Obama, and Holbrooke instead responded with a list of advisers he had ties to. “We have all worked together, Susan Rice, Tony Blinken for Biden, Greg Craig. I worked closely with all of Senator Obama’s current team. I know them well.”
But the truth was, Richard Holbrooke had precious little currency with Obama’s team. He had indeed worked with Susan Rice, during the Clinton administration. To say they didn’t get along would be putting it mildly. During one meeting, the feud got so bad that she flipped him the bird in front of a room full of staffers. Holbrooke allies in turn called her a “pipsqueak” with a “chip on her shoulder” in the press. Officials who worked with both said she felt Holbrooke had trampled over her. (“He tried to trample over me,” she clarified. “I don’t think he succeeded.”) Holbrooke’s relationship with Blinken, likewise, wasn’t enough to prevent his boss, Vice President Joe Biden, from telling Obama “he’s the most egotistical bastard I’ve ever met.” (Though Biden did admit Holbrooke was “maybe the right guy” to tackle the war in Afghanistan.) And Greg Craig, whom Holbrooke also listed, would soon fall out of favor with the Obama camp.
To many Obama loyalists, Richard Holbrooke was the enemy: part of the old guard of foreign policy elites that had accreted around the Clintons and dismissed Obama and his inner circle as upstarts. Holbrooke had avoided publicly criticizing the young senator from Illinois, but he had also leaned into his role as a Hillary loyalist, calling other foreign policy experts and signaling that support for Obama might mean throwing away job opportunities in a Clinton presidency (and, presumably, a Holbrooke State Department). Like much of the Democratic foreign policy establishment, he also wore the scarlet letter of his initial support for the war in Iraq. Later, he wrote and spoke about the disastrous repercussions of that invasion, including the neglect of Afghanistan. But in the eyes of many in the new administration, he remained exactly what Obama had run against.
There was also a divide of culture. Obama had run on excitement and change, not history or experience. He would later describe himself as “probably the first president who is young enough that the Vietnam War wasn’t at the core of my development.” When the United States finally pulled out of Vietnam in 1975, he was just thirteen, “so I grew up with none of the baggage that arose out of the dispute of the Vietnam War.” With a few notable exceptions, he surrounded himself with young men of the same generational outlook. Perhaps the most sustained and influential voice on foreign policy in the White House, Ben Rhodes, was given his bespoke role—deputy
