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 national security advisor for communications—at thirty-one. Staffers spent years swatting away a recurring comparison: White House as “frat house.”
In this White House, representatives of the dusty establishment were out of vogue. After a bruising race, Clinton loyalists were even less welcome—especially those with outsize personalities. “I think his whirlwind of activity, um, did cause some raised eyebrows in the White House,” Hillary Clinton said of Holbrooke. “They thought he was going outside the lines of the orderly policy process, the no-drama White House they were trying to run. And it was very painful for me.”
Two days after the election, Richard Holbrooke arrived in Chicago to interview with the president-elect. The meeting, which lasted thirty minutes, was an immediate disaster. According to friends Holbrooke called afterward. Obama greeted him as “Dick”—to which Holbrooke corrected him, saying that his wife, the writer Kati Marton, preferred that he be addressed as “Richard.” “That’s a joke, right?” Les Gelb, Holbrooke’s longtime friend who had involved him in the Pentagon Papers years earlier, recalled telling Holbrooke. “You didn’t really say that, did you?” It wasn’t. He did. Obama was annoyed—and later told several people so. “For some reason, President Obama thought he”—that is, Holbrooke—“had been treating him with some condescension,” Henry Kissinger said. “I do not know whether that’s true. But anyway, certainly Holbrooke had a lot more experience than the new people coming in.” In a sense, these were all characterizations of something simple: this was a job interview, like any other, and Obama just didn’t like the guy.
AMID THE SWEATY SCHMOOZING at the Fairfax on inauguration eve, Holbrooke was laser focused. Hillary Clinton becoming secretary of state was bittersweet, but also a reprieve. He would play a role in the administration. I watched as he and Clinton talked. He whispered in her ear. The two of them laughed. He made sure the assembled crowd saw it.
Clinton was at her most ebullient. The Obamas weren’t coming and she was the focus of every glance and whisper. She and I had attended the same law school, where several antediluvian professors spanned both of our enrollments. We’d met a number of times over the years, and she had always been kinder than she needed to be. Clinton had a preternatural knack for social recall, or at least artfully covering for memories she lacked. She professed to have read some of my foreign policy columns, and asked what I was doing next. I said I was deciding whether to go back to the law firm where I’d been a summer associate. She looked at me hard and said: “Talk to Holbrooke.”
She and Holbrooke had already begun crafting a new role for him, one she would later describe as, “by many metrics,” the most difficult in the administration. “Ever since my experience in Paris in 1968 as a junior member of the Vietnam negotiating team under Averell Harriman and Cyrus Vance,” Holbrooke once wrote, “I had wanted to test myself against the most difficult negotiations in the world.” He would get his wish.
WHEN HOLBROOKE’S ASSIGNMENT first leaked, the role was framed as “a special envoy for India, Pakistan and Afghanistan.” This was not sloppy reporting. Though his mandate was ultimately downsized to include only the latter two countries, Holbrooke had initially envisioned sweeping region-wide negotiations. “Afghanistan’s future cannot be secured by a counterinsurgency effort alone,” he wrote in 2008. “It will also require regional agreements that give Afghanistan’s neighbors a stake in the settlement. That includes Iran—as well as China, India, and Russia. But the most important neighbor is, of course, Pakistan, which can destabilize Afghanistan at will—and has.” In Bosnia, Holbrooke had juggled similarly fractious parties: not only Bosnian Muslims, Croats, and Serbs, but also Russia, the European allies, and organizations like the UN and NATO. Here, he again saw a need for a grand, strategic approach.
This ambitious plan for another Mission: Impossible–style political settlement built on old-school diplomacy quickly collided with the realities of the new administration. Two days after the parties on inauguration eve, Holbrooke stood in front of a crowd of current and former diplomats in the Benjamin Franklin State Dining Room, the grandest ceremonial chamber on the State Department’s eighth floor. The room was renovated in the 1980s in a classical style meant to evoke the great reception halls of continental Europe. Ornate Corinthian pillars, clad in red plaster and painted with faux-marble veins, lined the walls. Portuguese cut-glass chandeliers hung around a ceiling molding of the Great Seal of the United States: a bald eagle, one set of talons grasping a bundle of arrows, the other an olive branch. Holbrooke was flanked by Barack Obama and Hillary Clinton on his right, and Joe Biden and the administration’s newly appointed Middle East peace envoy, George Mitchell, on his left.
“It’s an extraordinarily moving thing for me to return to this building again, having entered it so many years ago as a junior Foreign Service officer,” he began.