Hillary Clinton sat in the hideaway study off her ceremonial office in the State Department, sipping tea and taking stock of her first year on the job. The study is more like a den—cozy and wood paneled, lined with bookshelves that displayed mementos from Clinton’s three decades in the public eye: a baseball signed by the Chicago Cubs star Ernie Banks, a carved wooden figure of a pregnant African woman, a statue of her heroine, Eleanor Roosevelt. The intimate setting lent itself to a less formal interview than the usual ones with Clinton in the nouveau opulence of her outer office, with its crystal chandelier, marble fireplace, and obligatory portrait of Thomas Jefferson, America’s first secretary of state. On the morning of February 26, 2010, however, Clinton was talking about something more sensitive than mere foreign affairs: her relationship with Barack Obama. To say she chose her words carefully doesn’t do justice to the delicacy of the exercise. She was like a bomb-squad technician, deciding which color wire to snip as the timer ticked down to zero.
“We’ve developed, I think, a very good rapport, really positive back and forth about everything you can imagine,” Clinton said about the man she had described during the 2008 campaign as naïve, irresponsible, and hopelessly unprepared to be president. “And we’ve had some interesting and even unusual experiences along the way.”
She leaned forward as she spoke, gesturing with her hands and laughing easily. There was more warmth than one had in exchanges with Obama, but less of an expectation that she might say something revealing. Clinton singled out, as she often did, the United Nations climate change summit in Copenhagen the previous December, where she and Obama had gate-crashed a meeting of leaders from China, India, and Brazil, and over the next seventy-five minutes persuaded the balky leaders to accept a nonbinding agreement that saved the summit from collapse. For Clinton and Obama, it was a bonding moment, proof that these former rivals could work together without a script.
It was also, in the tentative, early days of this rivalry turned partnership, extremely unusual.
A more telling anecdote, one Clinton never discussed publicly, had come six months earlier, in June 2009, when the new president traveled to Egypt to deliver a landmark speech to the Islamic world. Clinton was in the audience at Cairo University that day, drawing cheers and applause from the crowd that craned to see her as she entered the vaulted auditorium just before Obama, a handbag slung over her tan jacket. She had flown there overnight from a Latin American summit in Honduras, leaving in the middle of a rancorous negotiation over the diplomatic status of Cuba, so she wouldn’t miss the most important address of Obama’s young presidency. But the picture of solidarity belied a more complicated backstory: As the trip was getting under way, she had declined a request from the White House chief of staff, Rahm Emanuel, to peel off from the presidential entourage after the speech and fly to Jerusalem to meet with officials of Israel’s new government.
For weeks, the content and choreography of Obama’s big speech had been the subject of fierce debate inside the West Wing. Some of his advisers wanted him to seize the moment and lay down a new peace initiative for Israel and the Palestinians. Others disagreed, saying that in keeping with his pledge to wind down the Iraq War, his focus should be on a restart with the Islamic world. Some argued that Obama should visit Israel after Egypt to show America’s solidarity with its other main ally in the region. Others, including Ben Rhodes, said no, that would turn this historic gesture into yet another exercise in American shuttle diplomacy, diluting his message that a new era was dawning for the United States in the Middle East.
Obama opted not to go. Emanuel, worried that skipping over Jerusalem would bruise the feelings of the Israelis, proposed that Clinton do damage control. He went way back with Hillary, having worked for Bill Clinton’s campaign in 1992 and later in the White House as a senior adviser for policy and strategy. He and the First Lady had crossed swords during those years, but Emanuel had been there for the highs and lows of the Clinton presidency—from planning Bill’s first inaugural to helping draft the statement in which the president admitted his affair with Monica Lewinsky. Emanuel was also a staunch defender of Israel; he had once served as a civilian volunteer for the Israeli Defense Forces. Despite those credentials and their long history, when Emanuel asked Clinton to go to Israel in Obama’s stead and show the president’s commitment to a close ally, she turned him down cold.
“She couldn’t, wouldn’t, and didn’t,” said a former senior administration official who was told of the exchange.
Those in Obama’s inner circle thought her refusal smacked of self-interest, the reaction of a cabinet member who still thought and acted like an independent political figure. Clinton had her own long-standing ties to Israel and American Jews, and Obama’s demand that Israel halt the building of settlements in the West Bank, which she had faithfully delivered that spring, had already landed her in hot water with both. In those early days, with the bitterness of the campaign still a raw memory, some people in the West Wing concluded that Clinton was more concerned about protecting her flanks than the president’s. “There were times when it was like two principals,” the official said, “and each was judging it through the lens of their own interests.”
The lack of a high-level American visitor to Israel that summer would have lasting repercussions on the relationship between Obama and the Israeli government. Many in Israel never overcame their suspicion of the new president; his personal rapport with Prime Minister Benjamin Netanyahu, cool to start with, would deteriorate into mutual loathing. Not only did Obama skip Jerusalem, Israeli officials say, he gave them no heads-up about what his message would be in Egypt. “The Cairo speech is a foundational document,” said Michael Oren, who was Israel’s ambassador to Washington during much of the Obama presidency. “That it was given without any consultation with us is just amazing.” Among the president’s top aides, the episode came to be seen as a major unforced error. Emanuel refused to discuss any exchanges he had with Clinton on the subject, but he did admit that the Cairo trip had been mishandled. “I will take my fair share of lumps on it,” he told me. “You can’t go to the region and not go to your closest ally. Someone should have gone: the president, the vice president, the chief of staff, the secretary of state.”
Six months later, at the climate change summit in Copenhagen, it was Clinton who needed Obama to get on a plane.
She had gone to the meeting with mixed feelings. For days leading up to it, her advisers worried that she was walking into a minefield. There were deep divisions among the countries attending, and little hope of bridging them in time to produce an agreement. But Clinton had named a special envoy for climate change, Todd Stern, as a symbol of America’s resolve to join the fight against climate change, and he sent a memo to Clinton’s aides, urging that she come. Once there, Clinton found a situation so chaotic and dysfunctional that she likened it to an eighth-grade student council meeting. The summit had devolved into another grudge match between the developed and developing worlds. China, India, and Brazil were refusing to sign an agreement that would commit them to even incremental steps to curb emissions. Diplomats from 193 countries wandered the bright hallways of the Bella Center in a state of fretful entropy.
With failure looming, Clinton telephoned Obama and urged him to fly to Copenhagen to try to break the deadlock. His political advisers were opposed, not wanting to pull the boss away from a crowded domestic agenda for a diplomatic caper that looked as if it was going to end badly. Obama, though, had promised, like Clinton, to get serious about climate change. He trusted her diagnosis: that only the American president could broker a compromise. So on the evening of December 3, 2009, he ordered Air Force One fueled up for a flight to Denmark.
Twenty-four hours later, he was being briefed by an exasperated Clinton inside a small coffee bar in a shopping mall adjacent to the conference center that had been closed for the meeting. When it became clear that the Chinese delegation was trying to water down any agreement, holing up in a conference room with windows taped over to conceal their dealings from the Americans, Obama and Clinton decided to take matters into their own hands. They set off to confront the Chinese in person, fast-walking down a hallway and up a flight of stairs, panicked aides in chase, before they ran into a Chinese official in the doorway, waving his arms and shouting “Not ready yet.”
Confusion swirled as Clinton and Obama tried to find out who was in the room with the Chinese. An advance person told them it was the Indians, the Brazilians, and the South Africans. Now Clinton was mad: The Indians had told American officials they had already left for the airport. A major developing country was lying to avoid dealing with the United States on climate change? She and Obama looked at each other in disbelief. “C’mon, let’s just do this,” he said to Clinton. She moved first, ducking under the outstretched arm of a Chinese security guard and barging into the room, which drew a collective gasp from the leaders huddled around a conference table. Obama was right behind her. “Hi, everybody!” he bellowed, like a dad coming home early to find his teenage kids throwing a keg party in the backyard. “Mr. Prime Minister, are you ready to see me now?” he said, turning to face the nonplussed Chinese premier, Wen Jiabao, who was anything but.
Taking seats at the cramped conference table, Obama and Clinton began sketching out the terms of a deal like the lawyers they were, their aides scribbling on pieces of paper that they pushed back and forth across the table. The nonbinding agreement to monitor pollution reduction standards and set a goal to limit the rise in global temperatures was a mushy compromise, one that would look even mushier six years later, when nearly two hundred countries agreed to a binding deal in Paris. In the annals of global climate change negotiations, Copenhagen does not occupy a place of honor.
For Clinton and Obama, however, that hardly mattered. Copenhagen was a crucible for them personally, proof that they had finally put the past behind them. To Rahm Emanuel, the episode showed that whatever their past tensions, they shared an elemental bond: Both were political animals, attuned to the practices and prevarications of other politicians. And foreign policy, he added, is just another form of politics. “Yes, there’s history,” Emanuel went on, dropping his voice half an octave to mock those who would argue that a spat between superpowers is really all that different from a food fight between Chicago aldermen. “Someone did this or that four thousand years ago. But every person you’re dealing with is a person who’s dealing with politics.”
Copenhagen also drove home the sort of world Clinton and Obama would deal with over the coming years: messy, rife with shifting alliances, and hungry for American leadership, even if many resented that leadership. Though they often differed over how to assert America’s role, Clinton and Obama were united in the belief that preserving a lawful world order should be a paramount goal of the United States in the twenty-first century. “I think they each had an aha moment in Copenhagen, both with each other and in terms of looking at everyone else,” said Jake Sullivan, a thirty-nine-year-old lawyer who was Clinton’s top policy adviser at the State Department.
Decoding the relationship between Barack Obama and Hillary Clinton has never been simple. They did not indulge in public rifts or emotional displays of unity; both are too disciplined for that. There was less heartfelt affection than flows between Obama and Joe Biden, but more quiet regard than flows between Obama and John Kerry. They respected each other without ever losing the undercurrent of competition that charged their clashes on the campaign trail. The Hillary-and-Barack story is less a soap opera than a dynastic saga, a tale of thwarted ambition and painstaking cultivation. In that sense, Cairo and Copenhagen are bookends for a relationship that is both genuine partnership and enduring rivalry.
At the beginning, they used humor to defuse the tension between them. When Clinton shook hands with the Brazilian president, Luiz Inácio Lula da Silva, in April 2009, he confessed that he had never expected Obama to be elected president. “Well, neither did I,” she shot back. A few weeks later, Clinton returned from a visit to Mexico, then battling an outbreak of swine flu. “The second she got back from Mexico,” Obama said during a stand-up routine at the annual dinner of the White House Correspondents’ Association, “she pulled me into a hug and gave me a big kiss—told me to get down there myself.”
While Clinton and Obama managed to poke fun at the bitterness of the campaign, the Cairo episode demonstrated that it was harder for Clinton to get over it than it was for Obama. “It’s easier when you’re the winner to put things aside,” said David Axelrod, a veteran of the 2008 campaign who stayed on to advise the president and had his own complicated relationship with Clinton. “But Obama is not a vengeful person. He didn’t view her negatively. He viewed her as a friend who he had to run against.”
“There was a coolness right after the nominating process,” he continued. “I mean, it’s natural. Their first meetings probably were a little bit labored. But by the time she joined, it was a seamless transition.” Clinton had a tougher time letting down her guard with Obama’s aides, however. When Axelrod asked her office for her email address in June 2009, she clearly wanted to keep him at arm’s length. “Does he know I can’t look at it all day so he needs to contact me thru you or Huma or Lauren during work hours?” she replied to her chief of staff, Cheryl Mills, referring to her trio of close aides. Obama and Clinton still treated each other less as colleagues than as generals of rival armies that suddenly found themselves in an alliance of necessity. For the first few months, Joe Biden played the role of go-between, carrying messages from one camp to the other. “Hillary would say to me, ‘How do you think I should present this to the president?’ ” the vice president told me. “And I’d say, ‘Whoa, just present it to him.’ And Barack would say, ‘Does she know what a good job I think she’s doing?’ I’d say, ‘Just tell her.’ ”
Biden, however, had his own complicated relationship with Clinton. The two knew each other well and met regularly for breakfast at the vice president’s residence. But he could be condescending about her foreign policy experience, contradicting her in meetings and reinforcing the impression that she was the odd woman out.
Clinton, in fact, was far more isolated and unsure of herself in 2009 and 2010 than is commonly understood, several former aides said. She had trouble penetrating Obama’s clannish inner circle and struggled to adjust to his centralization of national security policy making in the White House. Her anxiety was reflected in the bewildered emails she sent to her aides, inquiring about what was going on at the White House. Her staff worried that she was demoralized. “Secretary of Awesome,” Cheryl Mills wrote on August 6, 2009, attaching a YouTube video of Clinton shimmying with the locals at a party in Nairobi, Kenya. “You shake your tail feathers girl!” she said. Plenty of Clinton’s subordinates sucked up to her for the usual reasons of self-advancement, of course. But emails like this one from Mills were meant, as much as anything, to buck up her spirits.
Clinton coped with the stresses of her situation by stocking the State Department with people loyal to her and focusing her energy on areas such as development and public diplomacy that would burnish her image without getting in the way of Obama. But that left the State Department even more peripheral—“like a Palestinian enclave in the middle of Israel,” in the words of one former official; “like the United States of Hillary,” in the words of another. That was particularly dangerous in this administration, which proved to be the most White House–centric of the modern era, run by a rigorously self-contained president who relied on a small circle of trusted advisers.
At times, Clinton seemed like a kid in a new school, trying to elbow her way into the popular clique. On the morning of June 8, 2009, she emailed two aides to say, “I heard on the radio that there is a Cabinet mtg this am. Is there? Can I go? If not, who are we sending?” On February 10, 2010, she dialed the White House from her home, but couldn’t get past the switchboard operator, who didn’t believe she was really Hillary Clinton. Asked to provide her office number to prove her identity, she said she didn’t know it. Finally, Clinton hung up in frustration and placed the call again through the State Department Operations Center—“like a proper and properly dependent Secretary of State,” as she later wrote to one of her aides in a mock-chastened tone. “No independent dialing allowed.”
In December 2009, rumors began circulating that the West Wing was maneuvering to oust Richard Holbrooke, her old friend and the special representative for Afghanistan and Pakistan. At the time, I called Jake Sullivan to check it out. He alerted Clinton, who asked him and Philippe Reines, her communications adviser, to see what they could find out. “People are deeply unhappy with our friend,” Sullivan confirmed to her. Reines wondered if the White House had leaked the story, hastening to add, “There’s no way they’d handle you that way.” Nearly a year into the administration, it was clear that Clinton’s people still did not entirely trust Obama’s people.
As hard as it was for Clinton, it was even harder for their staffs to reconcile. Both sides suffered from a kind of post-traumatic stress disorder. Tommy Vietor, who drove a press van in rural Illinois during Obama’s Senate campaign and later worked as his press secretary in Iowa, recalled that for months, the Obama and Clinton campaigns held daily conference calls with reporters in which they clubbed the other side in harsh personal terms. Every afternoon, he would pore over the Clinton transcripts, soaking up the attack lines like a toxin. “The people who went through that campaign manufactured a pretty visceral hatred for each other,” said Vietor, who went on to be the spokesman for the National Security Council. “You magnify differences and internalize grievances in a way that is ridiculous.”
When Clinton finally gave up and threw her support to Obama in June 2008, enemy combatants were forced to become comrades-in-arms. The Obama campaign hired prominent Clinton domestic policy advisers and folded together the foreign policy teams, making room for Clinton-era luminaries such as Holbrooke and Madeleine Albright. Friendships that had been put on ice for the previous eighteen months were reactivated. “It was weird because we wanted to rip each other’s throats out a few minutes earlier,” said Dan Pfeiffer, who was the Obama campaign’s communications director and later held the same job at the White House.
That weirdness did not compare to what happened days after the election, when the president-elect told his aides he was going to ask Hillary Clinton to be his secretary of state. The idea had been percolating for a while, advanced by John Podesta among others, so it was not a total surprise. But the prospect was still jarring. When Pfeiffer, a fast-talking Beltway operative who runs everything through a political calculator, first heard the choice, he recalled thinking it was “brilliant and dangerous.” On the one hand, Obama would bring his archrival into the tent, eliminating the prospect of her taking potshots at him from the Senate and short-circuiting speculation over whether she would challenge him again in 2012. On the other, he could not fire her without setting off a monumental political storm. That was no small risk for Obama to take, given their history and the bad blood between the two camps.
It also meant that Hillaryland—the Louis XIV–like court of advisers, staffers, supporters, fundraisers, and flatterers that she had cultivated—was going to take up permanent residence in Obama’s administration. Clinton, it seemed, was determined to find a place for every one of them. As a condition of taking the job, she extracted an unheard-of promise from Obama: that she could fill the political posts in the State Department. These plums, typically a president’s to hand out to his loyalists, instead went to Hillary to parcel out to hers. The only exceptions were ambassadorships and a handful of other posts, such as deputy secretary, which went to Jim Steinberg, an Obama adviser who nevertheless had once worked for Bill Clinton. Cabinet members are normally allowed to bring only a handful of close aides with them to their new job. A former aide to Bill Clinton recalled telling William Cohen, a Republican senator named defense secretary in 1996, that he could bring a single person with him to the Pentagon. Hillary ended up bringing close to one hundred to State.
Clinton’s hiring binge—which Obama honored despite the cavils of his own staffers—had far-reaching consequences for the State Department she was to run. Never before had the nation’s seat of diplomacy been so unabashedly political, with a constellation of Clinton-appointed special envoys and advisers, some of whom knew next to nothing about diplomacy. Ronan Farrow, the twenty-two-year-old son of Mia Farrow, advised Clinton on “global youth issues,” irritating the Foggy Bottom–dwellers who resented that he got prime real estate on the seventh floor, where Clinton had her office. Kris Balderston, a genial backslapper from upstate New York who had worked for her in the Senate, was put in charge of a new effort to create public-private partnerships. The politicos raised money to build a U.S. pavilion at the world’s fair in Shanghai; distributed clean-burning cookstoves to mothers in the developing world; created social networks for people from diaspora groups; and incubated a host of other projects. It was worlds away from writing cables or stamping visas, the traditional work of diplomacy done by the State Department.
Broadly speaking, these were the kinds of progressive social causes Clinton had championed since she left Yale Law School thirty-five years earlier—the building blocks of an activist worldview that would set her apart from Obama. “This is a woman who wants to elevate development to be equal with diplomacy,” said Anne-Marie Slaughter, a former dean of Princeton’s Woodrow Wilson School of Public and International Affairs whom Clinton recruited to run her Policy Planning shop. “It’s as much about human security as state security.” Slaughter codified the new approach in a classically Clintonesque document known as The Quadrennial Diplomacy and Development Review. She likened Clinton to the skipper of a World War II destroyer, trying to retrofit her aging vessel for the wars of today.
In the short run, though, Clinton’s hiring set off fights over personnel. It pitted her chief of staff, Cheryl Mills, a diamond-hard lawyer who had defended Bill Clinton during his impeachment trial, against Denis McDonough, the equally combative head of Obama’s foreign policy transition team, and occasionally against Rahm Emanuel. In 2009, Clinton offered the post of undersecretary of state for arms control to Ellen Tauscher, a Democratic representative from Northern California who had been a stalwart fundraiser for her and Bill. Tauscher, whose district contained two national weapons labs, knew her military hardware. But she had ousted a Republican incumbent in 1996, and Obama’s aides feared they would lose her district, which included a necklace of affluent East Bay suburbs of San Francisco. It didn’t help that Clinton had not told them of her plans in advance.
“You tell Hillary to go raise $500,000 to keep that seat Democratic,” Emanuel snarled at Mills, according to a person who heard the exchange. (The mayor said he did not recall the incident, though, he said, “It does sound like me.”)
Clinton was able to hire Tauscher, but she lost other battles. She wanted Joe Nye of Harvard—who coined the term “smart power,” which was to become her mantra at the State Department—to be ambassador to Japan. The White House preferred John Roos, a low-profile Silicon Valley lawyer and top-tier Obama fundraiser. And she was blocked from bringing aboard Sidney Blumenthal, the former New Yorker writer, White House staff member, and longtime Clinton-family retainer, whom she envisioned as a senior adviser parked in the Policy Planning division.
It was hard to know who hated the idea of Blumenthal more: the White House or the State Department. Obama’s aides regarded him as a conspiracy theorist who had practiced his dark arts against them during the campaign, planting negative stories about Obama’s private life. Clinton’s cadre of young staffers, some of whom knew Blumenthal only by reputation, viewed him as the Ghost of Clinton Past who would threaten their access to her. Even other Clinton political appointees questioned what he would bring to Policy Planning, which had been created in 1947 by George Kennan, architect of the Cold War containment policy, as an elite preserve for big thinkers. It fell to Emanuel, who had nicknamed Blumenthal “G.K.” (for Grassy Knoll) when they were both working in the Clinton White House, to tell Hillary he was persona non grata—a message he delivered not long after she declined to travel to Jerusalem. Turnabout, it seems, was fair play.
It hardly mattered that Blumenthal didn’t get a State Department building pass. He functioned as a shadow counselor throughout her tenure, sending her hundreds of emails—addressed to H—with advice on polishing her image, dealing with the Libyan war, fighting turf battles with the White House, even staying abreast of GOP politics. By turns high-minded tutor and down-and-dirty gossip, he was without peer as a correspondent. On Election Day in 2010, he told Clinton that House Speaker John Boehner was “despised by the younger, more conservative members of the House Republican Conference. They are repelled by his personal behavior. He is louche, alcoholic, lazy, and without any commitment to any principle.” In March 2010, he advised her to put a stop to David Axelrod’s freelancing in foreign policy, which he said had aggravated tensions with Israel. “Make Steinberg tell Donilon they need to rein in Axelrod,” he wrote, referring to Tom Donilon, who was then the deputy national security adviser. “Axelrod has enough to do fixing the domestic messes he’s made. Let it come from Steinberg. He’s unhappy anyway.” Blumenthal’s animus against Axelrod was really about Obama. He sent Clinton a steady diet of articles analyzing the flaws in the president’s foreign policy, his troubles passing his legislative agenda, and his eroding popularity.
As always, though, Blumenthal’s favorite project was Clinton herself. In July 2009, he sent her a long memo critiquing the draft of a speech she was planning to deliver at the Council on Foreign Relations. The speech, an ambitious blueprint for Clinton’s tenure, had been through countless rewrites at the State Department. Blumenthal took an acid pen to it. “There’s no accounting of progress so far,” he wrote. “The effect is downbeat in tone.” The speech, he said, was guilty of “blithe liberal cultural imperialism” in asserting that people everywhere want the same things Americans do. Most brutally, he advised Clinton to cut way back on her mantra, smart power. “Slogans can become shopworn,” he wrote, “especially those that lack analytical, historical or descriptive power.”
Of all the political staffers that Clinton brought with her to Foggy Bottom, none was as personally important to her—nor as emblematic of the tribal loyalties of Hillaryland—as Huma Abedin. Born in Kalamazoo, Michigan, and raised in Jeddah, Saudi Arabia, by an Indian father and a Pakistani mother, the thirty-three-year-old Abedin began working for Hillary as a White House intern in 1996 when she was still a student at George Washington University. A sleek, striking woman with a charming, if somewhat remote, manner and a taste for Louis Vuitton handbags, Abedin traveled everywhere with Clinton, keeping her on schedule and in hand sanitizer. So close had she become to both Clintons that Bill once toasted her as his surrogate daughter; a jet-lagged Hillary once emailed her at 12:21 A.M. to take her up on her offer to come over to her house for a chat. If she was dozing when Abedin arrived, Clinton emailed, “Just knock on the door to the bedroom if it’s closed.”
At a meeting early in 2009 in the State Department, Abedin, who had the title of deputy chief of staff, was going through a list of requests from “the president.” When the others in the room looked at her puzzled, she clarified, “Not President Obama. Our president. Bill Clinton.” It was a jarring gaffe, evidence of just how deep and tangled those ties were. And yet it was understandable: By the last year of the first term, Abedin was, in fact, working for both presidents. Under an arrangement that later caused political headaches for Hillary, Abedin kept working part-time for her at the State Department while accepting a lucrative contract from a private consulting firm with ties to the Clinton Foundation. No other Clinton aide enjoyed that kind of latitude. But Abedin’s offhand remark back in 2009 illustrated the challenges of working in the Obama administration for anyone raised in the Clinton ecosystem: They had to get used to staffing a staffer, not a president.
Jake Sullivan was rare in that he had straddled both worlds. This allowed him to play a vital role in the acculturation process. Brilliant, rail-thin, with a guileless mien that belied shrewd political instincts, Sullivan first showed his dexterous touch in 2008, advising Clinton on foreign policy during the primaries, then prepping Obama for his debates against John McCain. He shared the deputy chief of staff title with Abedin, but like her, he wielded outsized influence. If Huma was Clinton’s right hand, he was her left. He was at her side in all 112 countries she visited as secretary of state—an ever-present, increasingly spectral figure, in a blue fleece, his eyes often deeply ringed after pulling another all-nighter on the road. Clinton described him as a “coolheaded, clear-eyed analyst of the problems we faced with our national security.”
“He ended up being invaluable,” she told me.
Even by the best-and-brightest standards of Washington, Sullivan’s résumé is an overachiever’s dream: high school debate champion in Minneapolis; editor of the Yale Daily News in college; Rhodes Scholar at Oxford; Yale Law School, an alma mater he shared with Clinton and to which he returned to teach after leaving the administration in 2014; clerk to Supreme Court justice Stephen Breyer. Sullivan, like Clinton and Obama, has a lawyer’s cast of mind: He talks about having a “theory of a case” and dismisses flimsy arguments as “not dispositive.” He knows he’s often the smartest guy in the room. “It can feel like arrogance to say, ‘I have an idea,’ or ‘I can do that’—especially if you’re surrounded by smart and experienced people,” he once told graduates of the Humphrey School of Public Affairs at the University of Minnesota. “But that’s not arrogance. That’s being constructive.”
On Thanksgiving Day in 2010, Sullivan emailed Clinton to let her know he had circulated a call sheet to senior officials to develop recommendations for how she should handle Prime Minister Netanyahu on the phone the next day. “I’m taking a break from peeling potatoes,” Sullivan explained. (His emails, often on sensitive subjects, would later land him in the middle of the storm over Clinton’s use of a private email address and computer server while she was secretary of state.) Melanne Verveer, Hillary’s chief of staff in the White House and her ambassador for global women’s issues at the State Department, watched Sullivan in action on an overseas trip. Hours into the flight, when the cabin was dark and everyone else had dropped off to sleep, he was quietly speaking to the White House over a secure phone line. “Jake just never stopped,” she said. “Everybody else could be out cold, and Jake was working those phones.”
These qualities were not lost on Obama’s whiz kids, Denis McDonough and Ben Rhodes. Sullivan was to become the primary transmission belt between Foggy Bottom and the West Wing, between Hillaryland and Obama-world. He was crucial to easing Clinton’s isolation, especially with McDonough, a forty-six-year-old fellow Minnesotan, with whom he established a less contentious relationship than Cheryl Mills had.
A college football star from the town of Stillwater, where his nickname was “the Dude,” McDonough shares Obama’s lean frame, ascetic habits, and cautious worldview, forged in the post-9/11 era. He is an old-school Irish Catholic, prematurely gray, with a touch of the hair shirt about him—working brutal hours, giving up coffee and chocolate for Lent, biking the seven miles to work from his home in Takoma Park, Maryland, until his wife forced him to give it up after an accident. A family man who coached his kids’ soccer games while taking nonstop calls from the White House, McDonough could be uncommonly decent: He was known for his graceful notes to visitors and staffers. But he could also be hard on those around him, especially in the first year of the administration, when he bullied journalists and others who dared criticize his boss. He clashed with Sullivan, too, once laying into him for remarks he made at Obama’s daily briefing that McDonough thought undercut him. (Sullivan, friends said, was stung for days afterward.) For the most part, though, the two got along. Over hundreds of emails and phone calls, they worked to make sure Clinton’s public statements did not conflict with the White House.
With Rhodes, Sullivan developed a friendship that would prove fortuitous. Separated in age by a few months, they each had their boss’s ear and power beyond their years. The two are different: Rhodes is a city kid from Manhattan who smokes and likes a martini; Sullivan, a Midwesterner who drinks beer and roots for the Vikings and Twins. Rhodes is an idealist and a romantic (he has an unfinished novel in a drawer, “Oasis of Love,” about a woman who joins a mega-church in Houston, breaking her boyfriend’s heart); Sullivan is hardheaded and pragmatic. Rhodes thumbs his nose at the Clinton-era Democratic establishment; Sullivan is a card-carrying member of that establishment. And yet they hit it off, emailing or speaking several times a day. Often, it was over routine matters such as the wording of a Clinton statement; other times, it was to make history. The diplomatic openings to Burma and Cuba both had their roots in bull sessions between Rhodes and Sullivan, with Sullivan honing the concepts and Rhodes using his influence with the president to maneuver them through the risk-averse West Wing bureaucracy.
After Clinton left the State Department, she and the president would use their staffs—once the source of so much mutual enmity—to preserve a veneer of unity over how they had worked together and how they viewed the world. She gave parts of her memoir Hard Choices to Rhodes for review before publication to make sure her gentle airing of policy disagreements did not ruffle Obama. In early 2013, Sullivan became national security adviser to Joe Biden, a perch that allowed him to convey the White House’s sensitivities to her. To help with the rollout of the book, Clinton hired Tommy Vietor, the Obama loyalist whose jaundiced views of her had been formed by the poisonous transcripts he read back in Iowa. She won him over when he was the NSC’s spokesman, once sending him a sling with a State Department seal after he dislocated his shoulder while playing basketball. A quick study with an iPhone full of press contacts, Vietor was tasked with pushing back on reporters who would use the book to try to drive a wedge between her and Obama.
For much of Clinton’s tenure, the State Department and White House were tormented by the anonymous owner of a Twitter account with the handle @NatSecWonk. This mystery tweeter, who posted from inside the administration and amassed a small but devoted audience, ridiculed everyone from Rhodes to Reines to various New York Times reporters. Sample: “I’m a fan of Obama, but his continuing reliance and dependence upon a vacuous cipher like Valerie Jarrett concerns me.” Or, “Look, Issa is an ass, but he’s on to something here with the @HillaryClinton whitewash of accountability for Benghazi,” referring to Darrell Issa, the California Republican who plagued Clinton over the Benghazi attacks. @NatSecWonk was eventually unmasked as a forty-year-old NSC analyst named Jofi Joseph. He was sacked; he issued an apology and since has become a cautionary tale for using social media in the workplace, when your workplace happens to be the White House.
Before his fall, though, @NatSecWonk had Clinton squarely in his crosshairs, tweeting that she had “few policy goals and no wins” as secretary of state. It was a harsh verdict, but in the years after she stepped down—when John Kerry was a whirling dervish of activity, negotiating the Iran nuclear deal, seeking a political settlement in the Syrian civil war, trying to revive the Middle East peace talks—it was not an uncommon one. By comparison to Kerry, Clinton’s record looked meager; her approach, cautious; her achievements, evanescent. @NatSecWonk was simply voicing what a number of people in the White House and State Department privately thought: Hillary Clinton had been a respectable but run-of-the-mill secretary of state.
Assessing Clinton’s record requires a couple of stipulations. The first is that few secretaries of state in the modern era have compiled a spectacular list of wins. Henry Kissinger, the most famous of them, engineered the secret opening to China and negotiated the Paris Peace Accords, which ended direct American combat in Vietnam and set the stage for the war’s messy final act. James Baker, arguably the most effective of them, helped steer the Cold War to a peaceful end, assembled a robust coalition for the Persian Gulf War, and orchestrated the Madrid peace talks between the Israelis and Palestinians, which became a model for future Middle East peace negotiations. Warren Christopher, Madeleine Albright, and Condoleezza Rice had no comparable achievements, while Colin Powell is remembered most for brandishing a vial of white powder in the UN Security Council and claiming, erroneously, that Saddam Hussein had weapons of mass destruction.
Even John Kerry’s busy tenure has earned a mixed verdict, with his failed Middle East peace campaign balancing his breakthrough with Iran. Kerry, moreover, was blessed with timing: Clinton spent her first two years in a largely symbolic global rehabilitation tour for the United States, patching up relationships frayed by George W. Bush’s invasion of Iraq. Then she was tasked with lining up the international sanctions that eventually forced the Iranians to the bargaining table. As Clinton somewhat plaintively put it, she “set the table” for Kerry’s diplomatic banquet.
“For better or worse, we have sort of a heroic vision of diplomacy,” Jim Steinberg told me. “Henry Kissinger is the epitome of this. But it’s easy to overwrite the traditional role of leader-to-leader diplomacy. That’s especially true in the twenty-first century, because the role of the state has changed.” Clinton confronted a world that was more complicated than Kissinger’s or Baker’s—one in which a medieval Islamic caliphate conquered large parts of Iraq; in which the United States no longer faced a single Cold War rival but rather a babel of rising powers; in which economic and environmental factors, such as joblessness in the Middle East and rising seas in the Pacific, drove events as much as geopolitics.
A second stipulation is that a secretary of state’s clout derives almost wholly from his or her relationship with the president. To the extent that the secretary is seen as a confidant or, better yet, a proxy of the commander in chief, he or she can get things done. Kissinger spoke to Richard Nixon several times a day, more than anyone else in Nixon’s cabinet. “Shared personality traits made [them] effective collaborators,” Robert Dallek wrote in his book Nixon and Kissinger. “Their combative natures made them distrustful of others, whom they suspected of envy and ambition to outdo them.” Jim Baker was George H. W. Bush’s consigliere before his cabinet officer, a status that gave him muscle in Washington and credibility abroad. “Baker used to say that he was President George H. W. Bush’s man at the State Department, not the State Department’s man at the White House,” said Aaron David Miller, who served as an adviser to Baker and other secretaries of state.
Neither of those models was ever going to apply to Clinton and Obama. She would never have described herself as Obama’s woman at the State Department. Clinton was a world figure coming into the job, with celebrity and a Rolodex of contacts that rivaled or exceeded Obama’s. Nor did she have the deep familiarity with the president—the round-the-clock, backchannel access—that Kissinger had with Nixon. “I see the president when I need to see him; I talk to the president when I need to talk to him,” Clinton told me, a bit defensively. She was clearly sensitive that outsiders would make unflattering comparisons. In December 2009, when she was considering a request from Newsweek for a joint interview with Kissinger, Clinton raised a potential red flag with her press aide, Philippe Reines. “The only issue I think that might be raised is that I see POTUS at least once a week while K saw Nixon every day,” she emailed. “Of course, if I were dealing with that POTUS I’d probably camp in his office to prevent him from doing something problematic. Do you see this as a problem?”
The formal, unequal nature of her relationship with Obama was perhaps best summed up by the importance she attached to their weekly meeting in the Oval Office. On a snowy Thursday morning in February 2010 when she was scheduled to meet the president, Clinton got an alarming phone call: Her husband Bill had been admitted to NewYork–Presbyterian Hospital with chest pains, and was in need of an urgent heart procedure. Instead of rushing home to him, Clinton kept her weekly appointment, taking her customary seat on the yellow sofa as she and Obama talked about an upcoming trip to the Persian Gulf, where she planned to turn up the heat on Iran over its nuclear program. “No one had any idea” she had a family emergency, said an official who was in the room that day. Afterward, she raced for a shuttle flight back to New York.
Further complicating life for Hillary, Obama brought an overweening self-confidence to the Oval Office. He was more than ready to answer the three A.M. phone call—the punch line from Clinton’s famous attack ad—without putting her on the line. His tight grip was most evident on marquee foreign policy portfolios such as Iran and Russia. He had befriended Dmitri Medvedev in the hopes that a high-level bromance with the young Russian president might usher in a new era of goodwill. He wrote secret letters to Iran’s supreme leader, Ayatollah Ali Khamenei, to entice the suspicious mullah into a dialogue. Obama handed the Iraq file to Joe Biden, a decision that Clinton did not contest because she viewed it as a loser. Even on issues that are supposed to be in a secretary of state’s wheelhouse—peace talks between Israel and the Palestinians, for example—the White House set the strategy and Clinton was less an architect than an implementer.
Obama sanctioned the consolidation of foreign policy decision-making inside the West Wing. By 2010, the National Security Council staff had grown to 370 people, more than ten times its size under Kissinger. As it grew, it expanded beyond strategy into the day-to-day operations traditionally handled by the State Department and other agencies. Some of that reflected the addition of the Homeland Security Council, a post-9/11 creation that advises the president on terrorism or other threats. But a lot of it simply represented the secular shift of power away from the Harry S. Truman building, home of the State Department, to the Eisenhower building, home of the NSC.
So well-established was the Obama White House’s penchant for control that when Antony Blinken—a suave, well-pedigreed adviser to Biden who later became the deputy national security adviser—moved to the State Department to be deputy secretary in January 2015, he knew just how to break the ice with his new colleagues at his first staff meeting. “I’ve been here one day and I’ve come to one conclusion,” Blinken told them with a grin. “This micro-management of the inter-agency process by the White House has got to stop.”
Clinton’s aides pooh-poohed the notion that she was plotting a run for the White House from Foggy Bottom and shaping her tenure as secretary of state to further that ambition. But in some ways, she never stopped behaving like a candidate. Her emails show she kept a close eye on the political machinations of would-be rivals such as Joe Biden, Jim Webb of Virginia, and Andrew Cuomo of New York. She made time to speak to marquee Democratic donors such as Steven Spielberg and less well-known, but important, figures such as Lou D’Allesandro, a state senator from New Hampshire who had been a cochairman of Italian-Americans for Hillary in 2008. When one of her former policy advisers, Neera Tanden, asked her in early 2012 whether she should hold a reunion for alumni of the campaign, Clinton gave it her blessing. “I am very proud of all they—and we—did,” she replied. “Onward!”
Tanden emailed Clinton with regular updates on one of her pet issues: the epic battle to overhaul the nation’s healthcare system. At one point, she noted that Obama’s legislation was moving closer to what Clinton had pushed in the campaign. (“If it does break that way,” Tanden wrote, “I’ll try to ensure I’m not the only one who notices.”) When the bill was a few votes short of passage in the House in November 2009, a desperate White House enlisted Clinton to lobby two Blue Dog Democrats from Arkansas who were holding out (one switched his vote to a yes). On the morning of Christmas Eve in 2009, Clinton told a State Department colleague, she woke up early to watch the Senate hold a seven A.M. vote on the legislation. It passed 60 to 39.
Even Clinton’s diplomatic efforts sometimes felt like a political campaign. When she first traveled to Beijing in February 2009, for example, Clinton got an earful from the Chinese about how the United States might not be represented at the Shanghai Expo the following year because it had not raised the money to build a national pavilion. “I was dumbfounded that so little attention had been paid to it,” she told me. “Everyone knows China is going to be an enormously powerful player in the twenty-first century. They have an expo, which is a kind of rite of passage that countries like to do to show they have arrived. We’re not there? What does that say?”
Her solution was to reactivate the Clinton fundraising network. Elizabeth F. Bagley, a prolific bundler—and the widow of the R. J. Reynolds heir Smith Bagley—had been installed at the State Department as one of her special advisers. She began calling around to the chief executives of PepsiCo, General Electric, and Chevron, asking for multimillion-dollar pledges and dangling sponsorship deals. “Great news from Chevron!” Bagley wrote in an email that was forwarded to Clinton, after the oil company committed $5 million to the $60 million project. Chevron’s CEO, David O’Reilly, had promised Clinton in a letter that he would help. The State Department’s lawyers were queasy—“Would Thomas Jefferson do this?” one asked—but they signed off, provided that Clinton did not personally squeeze anyone for cash.
Evidently, their queasiness did not extend to the American ambassador. Clinton’s office asked Jon Huntsman, a former Republican governor of Utah whom Obama appointed as his envoy to China in 2009, to dial for dollars as well. The scion of one of Utah’s richest families, Huntsman had won two terms as governor. (He later came back from Beijing in 2012 to run a long-shot bid for the GOP presidential nomination.) Though he endorsed Clinton’s effort, he refused to take part in it. “I didn’t want McNerney from Boeing coming into the office saying, ‘OK, we gave you five million bucks for the Expo, we need some help on 757 orders,’ ” he said, referring to Boeing’s chairman, James McNerney. “I just never wanted to be put in that position. Nor did I want to put them, the CEOs, in that position.”
It didn’t matter: Clinton’s star power alone was enough to raise nearly $55 million in less than nine months. The following May, she traveled to Shanghai to see the House That Clinton Built, otherwise known as the USA Pavilion. It looked like a rental-car center at a big-city airport, with matte-gray walls and relentless corporate shilling inside (videos showcasing representatives from Chevron, General Electric, and Johnson & Johnson; environmentally friendly features sponsored by Alcoa; a gift shop with licensed merchandise from Disney). “It’s fine,” Clinton replied, lips pursed, when I asked her what she thought of it. “Can you imagine if we had not been here?”
During the last two years of her tenure, Clinton did less of this feel-good public diplomacy and more of the heavy lifting on sensitive issues such as Syria, Libya, Iran, China, and the periodic clashes between Israel and Hamas. Still, she was never going to be at the heart of the Obama foreign policy machine, and she knew it. That helps explain her aggressive focus on development while secretary of state. The grab bag of social projects that she embraced was one way to compensate for the limitations she faced in the traditional realm of national security. Clean-burning cookstoves, diaspora engagement networks, women’s and girls’ rights, the Shanghai Expo—it all added up to what Aaron Miller called “planetary humanism.”
Planetary humanism, it must be said, did wonders for her public image. “Hillary Clinton’s Last Tour as a Rock-Star Diplomat,” was the headline of a New York Times Magazine profile in June 2012, which opened with her inspecting an exhibit of cookstoves in China. She was celebrated in gauzy profiles in Vogue and Elle, a run of good press unmatched in her political career. (Her first Times Magazine profile, in 1993, carried the headline “Saint Hillary,” and it was not meant as a compliment.) The polarizing figure of the Clinton White House and the 2008 campaign had become the cool customer in oversized dark sunglasses, reading her BlackBerry on a C-17 military plane about to take off for Tripoli. That photo of her, taken in 2012, went viral on the Internet, giving rise to a popular meme, “Texts from Hillary.” (Obama: “Hey Hil, Whatchu doing?” Clinton: “Running the World.”)
Clinton’s emails confirmed the suspicions of those of us who covered her: She and her aides had a campaign-like obsession with her image and press coverage. Poll numbers were analyzed as if the secretary of state were always about to face the voters in New Hampshire. In March 2011, Reines sent Clinton an email with the subject line, “65%!” He was referring to her favorability rating in the latest CNN poll, which was near her all-time peak. “This is why we cooperate with so many profiles,” he explained, “and just wait until 19 million people read People next week.”
The White House never stopped viewing Clinton through a political prism, either. On November 14, 2012, Israel began an intense air campaign against Hamas militants in Gaza in retaliation for rocket attacks on Israeli cities. A ground invasion loomed. Clinton was in Asia with Obama on what had become a farewell tour for the two of them. She told the president she thought she should fly to the region immediately to try to broker a cease-fire. Clinton had not come to the decision easily; the risks of failure were great and the consequences of thrusting herself into the middle of it unpredictable. As Obama and his aides debated whether to send her, however, the conversation turned to a familiar theme, according to a person who witnessed the exchange: Was Clinton just doing this to make herself look good?
Ironic, in that three and a half years earlier they had viewed Clinton’s refusal to travel to Israel as proof of her political gamesmanship.
They sat side by side in the White House, he in a dark blue suit and tie, she in a raspberry jacket with turned-up collar, the camera lights reflecting off the prescription eyeglasses she had worn since suffering a concussion from a fall in her home. It was January 25, 2013, four days after Obama had been sworn in for a second term, and seven days before Clinton was to step down as secretary of state. The occasion was a joint interview on 60 Minutes, the first time Obama had appeared on the program with anyone other than his wife. For all the attention it got at the time, the interview shed little light on the deeper mysteries of their partnership. Clinton laughed off a suggestion that anyone should read their appearance together as a preemptive endorsement for 2016. Obama paid tribute to her for reinvigorating the role of secretary of state and reminisced about their diplomatic derring-do in Copenhagen in 2009.
“I consider Hillary a strong friend,” he replied, when asked how he would describe their relationship.
“I mean, very warm, close,” Hillary said, leaning forward and gesturing with her hands, as she tried to offer more than a six-word answer to the question. “I think there’s a sense of understanding that doesn’t even take words because we have similar views, we have similar experiences that I think provide a bond that may seem unlikely to some, but has been really at the core of our relationship over the last four years.”
The backstory, as usual, was more revealing.
Obama had asked his staff to look for ways he could thank Clinton publicly for her service in his cabinet. Ben Rhodes suggested to Philippe Reines that they do a joint interview in Time magazine; Reines countered with a joint appearance on 60 Minutes. He had a bias for television over print and he already had been talking to one of the program’s correspondents, Scott Pelley, about a one-on-one exit interview with Clinton. Pelley knew her well; he had traveled with her to Afghanistan in 2009 to report on the challenges she faced as secretary of state. The White House agreed but insisted that the interview be conducted by another 60 Minutes correspondent, Steve Kroft, a favorite of Obama’s. As a gesture, the president’s offer was both magnanimous and controlling, a handy metaphor for two partners with their own agendas.
The choice of Kroft also carried a strange echo: Twenty years earlier, Kroft had asked Bill Clinton about his marital infidelities in a famous joint interview with Hillary on 60 Minutes. It was, in many ways, her debut as a national public figure. As Obama and Clinton sat together, their conversation was a reminder that not only did she likely have a longer political future than he, but she also had a longer past—one that stretched back to 9/11 and the Iraq War, the storms of the Clinton years, and the 1992 campaign, when she had perched on a couch next to Bill, helping him save his campaign. At that time, Barack Obama was a thirty-year-old bachelor in Chicago, armed with a law school degree and a sense of destiny strong enough that he had already begun work on a memoir. His life story bore little resemblance to hers.
To understand the relationship they would forge, it helps to go back to their roots, to the different worlds in which they grew up and the different worldviews they acquired there.