NEW HAVEN, Conn. — If all had gone as planned, and as most in Washington had expected, Jake Sullivan would be hard at work just steps from the Oval Office.
He was the elite of the Washington elite: Rhodes scholar, Yale Law School graduate, clerk to a Supreme Court justice, the person at Hillary Clinton’s side when she circled the world as secretary of state, a steady voice in the Situation Room for President Barack Obama.
The conventional wisdom held that Sullivan was a lock to be the national security adviser in a Clinton administration. At 40, he would have been the youngest to hold that position in U.S. history.
Instead, Donald Trump won the presidency, and Sullivan says he sometimes feels like a “ghoulish reminder” to friends of an election that shook the Washington establishment like no other in decades.
On a recent evening, he was pushing open a battered orange door, climbing stairs covered with fraying carpet and striding into a dimly lit apartment where two dozen Yale Law School students were waiting to hear from him. Most of them were desperate for some version of the life he had led in Washington.
Sullivan, though, has never felt less certain about where both he and his country are headed. He divides his time between an empty think-tank office in Washington and Yale, where he lectures one day a week on law and foreign policy. Almost everything about his professional life is transitory, uncertain, unsettled.
“I feel a keen sense of responsibility for the outcome,” he told friends in the immediate aftermath of Clinton’s defeat. Months later, the feeling had not faded.
Clinton and others in her innermost circle of advisers often speak of the election as if it had been stolen from them. They rage against Russian interference, complain about the last-minute disclosures by former FBI director James B. Comey, and criticize Obama’s unwillingness to take a more forceful line with Russian President Vladimir Putin.
“Remember, I did win more than 3 million votes [more] than my opponent,” Clinton said in a recent interview.
Sullivan, more than most in the Clinton orbit, has begun to shoulder blame for the loss and his role in it. He wants to understand his mistakes and figure out how to fix them.
“I have the humility of the defeated,” he says as if it were a mantra.
On this night, Sullivan settled into a ragged, hand-me-down chair at the front of the Yale student apartment and looked around at the room full of smart, ambitious young people. He balanced a plate of greasy pizza on his lap. Someone handed him a beer.
“You all know Jake Sullivan,” a second-year law student said by way of introduction.
Everyone involved in Washington policy knew Jake Sullivan, or at least they knew of him.
For years he had been discussed as the next in a long line of gray-suited Washington wise men dating back to the end of World War II. The late diplomat Richard Holbrooke insisted that he had all the makings of a future secretary of state. Clinton confided to friends that she thought he could be president.
Sullivan gazed out the window down Hillhouse Avenue, a stretch of road that Mark Twain had called “the most beautiful street in America,” and in the direction of the apartment — three blocks away — where he had lived as a law student in the early 2000s. The students were clad mostly in jeans and sweatshirts. Sullivan wore the uniform he favors when outside of Washington — suit pants, a solid button-down dress shirt and no tie. His hair was combed in a ruler-straight part.
He ran through a list of his early mentors who had helped him find purchase in Washington: There was Leslie H. Gelb, the former president of the Council on Foreign Relations, where Sullivan had spent time as a summer intern, assigned by happenstance to Gelb’s office.
There was Strobe Talbott, who runs the Brookings Institution. In 2000, when Sullivan was starting law school, Talbott had just been chosen to lead the newly formed Yale Center for the Study of Globalization. “Those were the heady days when the mainstream foreign policy consensus was that globalization was a force for good,” Sullivan recalled. He had sought out Talbott after learning that they had both been Rhodes scholars and edited the Yale Daily News.
There was Holbrooke, who on Gelb’s recommendation had suggested Sullivan to Clinton when she was running for president the first time. And finally, there was Clinton herself, who adored and trusted Sullivan and had made him part of her innermost circle of advisers.
“It’s about seizing opportunities and saying ‘yes,’ ” Sullivan said of his career and two unsuccessful Clinton presidential runs. He paused and added wryly: “If you do that, you can take part in not one but two election catastrophes.”
Clinton tapped him in 2012 to help start secret talks with Iran over its nuclear program, and when she left government, Obama brought him to the White House, where Sullivan was part of the small group in the Oval Office each morning for the president’s daily intelligence briefing.
The students peppered Sullivan with questions about the Iran negotiations. Those questions, though, were largely a prelude to the subject that was really on their minds: the election, its aftermath and the long-term prospects for people like them in Washington.
“We were all devastated by the election,” a third-year law student said. “Have you bounced back?”
“If fill-in-the-blank Republican had won, I would feel like things were pretty good for me,” Sullivan replied.
For the first time in a decade, he had weekends off. He loved teaching. He was newly married. “But, the Trump factor makes it hard,” he said. “I am still losing sleep. I’m still thinking about what I could have done differently.”
Another law student pressed harder on the wound. “Do you have a theory about what happened?”
“I don’t know,” Sullivan said. He paused and stared at the ceiling.
“You don’t have to . . .” the student added, fearful that he had pushed too far. Sullivan considered his answer for a few more awkward seconds.
“It’s a conversation for better pizza,” he replied.
In other forums and at other dinners Sullivan was sometimes willing to wrestle with a version of the student’s question. At the Harvard Faculty Club a few weeks earlier, a former British parliamentarian, who in 2015 had lost his seat to a 20-year-old Scottish Nationalist, described the problem as he saw it.
“It’s a fight between politicians with answers and politicians with anger,” he had said.
“I get PTSD just hearing that,” Sullivan had replied.
Sullivan’s post-traumatic stress disorder that night led him to flash back to an argument with Clinton on her campaign plane. He was her senior policy adviser but was worried that her prescription-heavy speeches were missing the point of the election.
“Maybe we should just focus on diagnosing the problem and relating to people’s pain?” he recalled suggesting to her during her primary battle with Sen. Bernie Sanders of Vermont.
“No,” Clinton had replied. “This is a job interview. People want to know how I am going to fix it.”
Sullivan said he regrets not pushing the issue, even as it became more and more evident that the general election wasn’t going to be decided on policy.
In the campaign’s final days, Sullivan was more nervous than most on the Clinton team that the election was slipping away. His colleagues chalked it up to his fretful and frequently self-critical nature. “He has a tendency to wear the hair shirt,” one former colleague said.
Now Sullivan wonders whether he should have pressed Clinton harder to dial back the policy prescriptions in favor of empathy or possibly even a little outrage. “I mean, ‘Build the wall’ is not really a policy solution,” he said. “It’s a statement that gets to the heart of people’s concerns about immigration and . . . identity.”
But, before he goes too far, a defensiveness of Clinton and his role in the campaign takes hold. “It’s all about telling people that you get what they are going through and Hillary was certainly capable of that and had some incredible moments and displays of that,” Sullivan continued. He played down the significance of his exchange with Clinton on the plane.
“That’s more of campaign tactics issue,” he said.
Sometimes when he’s searching for answers, Sullivan thinks back to the fourth night of the Democratic National Convention, when Khizr Khan, whose son was killed in Iraq, pulled a pocket-size Constitution from his suit jacket and scolded Trump for trampling America’s highest ideals.
“We had our answer,” Sullivan told the Yale students. “The flag signified a great country, an inclusive country, a generous country.”
But the campaign never succeeded in turning that moment into a unifying message, and the presidential debate soon returned to divisive issues of race, immigration, inequality, abortion and transgender bathrooms, he said.
“I used to believe we just needed to take that night and stretch it over the span of the campaign,” Sullivan said. “But that’s not a solution, because you still have to deal with real issues. Our agenda involves a lot of ideas that are still controversial.”
Sullivan was going on about the “growing” and “scary” divide in the country when a law student from a rural town in Kentucky interrupted his monologue: “Coming from a flyover state, it is difficult for me to even be on the same wavelength as the people I grew up with.”
The student’s confession brought Sullivan back to his own upbringing in Minnesota. He was 13 when the Berlin Wall fell in 1989. A few months later, Soviet leader Mikhail Gorbachev, eager to meet with some average Americans, visited a home in Sullivan’s Minneapolis neighborhood. Sullivan remembered Latvian and Estonian Americans protesting for Baltic independence along the Soviet premier’s motorcade route. He felt a sense of what America could mean to the world.
As a candidate, Trump had rejected the very idea of American exceptionalism as an unnecessary burden. “I don’t think it’s a very nice term. We’re exceptional. You’re not,” Trump had said at a tea party rally in Texas. “I want to take everything back from the world that we’ve given them. We’ve given them so much.”
Sullivan increasingly thought that the antidote to Trumpism was a full-on embrace of American exceptionalism of the sort he had felt in Minnesota. “We need something audacious that’s rooted in our national DNA; who we are as a people,” he said. “There needs to be a call to arms that can motivate people.”
But he struggled to describe his idea in detail. To spur his thinking, he read a dense 1890 essay by military strategist Alfred Thayer Mahan, making the case for America as a global naval power. He studied historian Stephen Kinzer’s book, “The True Flag,” on Theodore Roosevelt, Mark Twain and the birth of the American empire.
He played with ideas that he hoped might resonate in Minnesota or Kentucky. “Our exceptionalism is rooted in the idea that we have the ability to innovate and solve hard problems — climate change, pandemics, nuclear proliferation,” he posited at one point. Maybe America’s exceptional mission was rooted in an unshakable commitment to a strong and growing middle class, he suggested a few weeks later.
But none of these formulations seemed big, audacious or inspiring enough.
Sullivan often insisted that he had developed his views about the world at “a public high school in Minneapolis.” But he is also unquestionably a product of Washington’s insular foreign-policy elite.
Even as partisan rancor took hold in the country, these Republican and Democratic internationalists had long insisted that they were different. They agreed on the biggest issues: The United States had a unique moral authority in the world and bore a special leadership burden. Almost the entirety of the Republican foreign policy establishment had signed letters opposing Trump’s candidacy.
Sullivan embodies many of these elites’ courtliest qualities. He does not shout down opponents or even tweet. Many Republicans have kind words for him. “He has a huge amount of integrity,” said Mark Dubowitz, an outspoken critic of the Iran nuclear pact. “You don’t get talking points and an unwillingness to acknowledge problems from him.”
As a candidate and even in office, Trump challenged just about every foreign-policy piety. He trash-talked America’s alliances, questioned the wisdom of nuclear nonproliferation efforts and rejected the ideal of a U.S. foreign policy built around democratic values, human rights and enlightened self-interest.
The response from Washington barely resonated outside of the Beltway. “We believe that abandoning traditional U.S. support for the international order would be a serious strategic error that would leave the United States weaker and poorer, and the world more dangerous,” read a recent Brookings report put together by a team of Washington luminaries that included Sullivan.
Lately, he had begun to question the worth and wisdom of these efforts. For years, the foreign-policy establishment has preached the importance of sustaining the U.S.-led, rules-based international order — an exhortation that, at best, was meaningless to most Americans. At worst, it smacked of soulless globalism.
To Sullivan, the most striking example of the establishment’s intellectual exhaustion was the mammoth 12-nation Trans-Pacific Partnership trade deal that Trump officially abandoned earlier this year. Republican and Democratic national security analysts for years had touted the pact as essential to U.S. national security and containing China. Sullivan had supported it, too.
But few of those experts, he said, paid any attention to the details of the pact and its potentially negative effects on American workers. Instead, they assumed that free trade was a net positive and focused on other issues, such as maritime disputes over island chains in the South China Sea, Sullivan said. In the process, the elite lost touch with the concerns of the very people it was supposed to serve and defend.
The gulf, Sullivan insisted, was symptomatic of a much larger problem.
“How do we solve for this basic and growing division in our society that gets to issues like dignity and alienation and identity?” Sullivan asked. He caught the eye of the young law student from Kentucky, sitting just a few feet away from him. “How do we even ask the question without becoming the disconnected, condescending elite that we are talking about?” Sullivan asked.
The question hung in the air.
Sullivan began to think recently that he could more easily answer these questions if he moved away from places such as Washington, Harvard or Yale.
“That’s not a value statement about who constitutes the good people of the land,” he said in an interview. “I don’t think that by going to live in Minnesota or New Hampshire or Tulsa, all of a sudden you’re gaining wisdom you can’t gain elsewhere. But you do gain a perspective. You’ll see things from a different vantage point, and that matters.”
Sullivan’s first move when he finished his Supreme Court clerkship in 2005 was to return home. He had turned down a $250,000 signing bonus from a big firm in Washington to accept a position with a smaller law practice in Minneapolis that focused on the agriculture and food industries.
Back then, he imagined a life split between government service in Washington and a more normal existence in Minnesota. “In Washington everything is built around the job because the jobs are all-consuming,” he said. “In Minnesota the job is one aspect of your life.”
Sullivan had planned to move back to Minnesota in 2013 when Clinton left the State Department. He was thinking about running for Congress or becoming a U.S. attorney, but Obama persuaded him to come to the White House. “Obama’s pitch was that you can always go home,” said Ben Rhodes, a top foreign-policy adviser to the president at the time. “That’s never going away, but here’s an opportunity to work at the highest levels of the White House and you never know when that’s going to come around again.”
Even after he finished his White House job, Sullivan remained tied to Washington through the Clinton campaign and through his wife, who is scheduled to begin a clerkship with Supreme Court Justice Stephen G. Breyer that will keep them in the nation’s capital for at least another year.
Then the plan is to leave Washington next year and settle someplace where he can put down roots. He imagines becoming involved in community projects where the results will be more real, immediate and tangible. Minnesota is one option. New Hampshire, where his wife grew up, is another.
The other possibility is that he stays. “I have given up hope of looking people in the eye and telling them we are moving anywhere, based on the last decade,” Sullivan said.
It’s rare for anyone at Sullivan’s level in the foreign-policy world to leave Washington or return home. The issues have become too complicated. The money is too good. One Asian country recently offered Sullivan $25,000 for a two-day visit.
“What’s that all about?” he recalled thinking before turning it down.
The Yale students’ worries, meanwhile, ran in the opposite direction. They fretted about the opportunities still available to people like them in Trump’s Washington.
“Is this the death knell of the technocracy and the elite?” one student asked, summarizing the thesis of a recent widely read article in Foreign Affairs magazine.
Before Sullivan could answer, another student clarified: “Is there a coastal elite 2.0, or are we all finished?”
Sullivan wasn’t the sort to succumb to the prophecies of doom that had taken hold in some sectors of Washington and academia. Even Trump still depended on his own version of the Washington elite, Sullivan told the Yale students. The president leaned heavily on generals to execute his foreign policy; his Cabinet was stacked with billionaires. “Goldman Sachs is running our economic policy,” Sullivan said. “So there will always be a demand for expertise.”
Sullivan’s evening with the Yale students was nearing its end. The sky outside had grown dark. His slice of pizza was cold on his plate.
“I still believe passionately in finding a home outside of D.C.,” he said.
“Virginia or Maryland?” one of the Yale students joked.
“Maybe,” he continued, “the best service I can render right now is outside of Washington.”
Sullivan edged toward the door. The next day he planned to meet with Clinton in New York to review her memoir, and maybe, if they finished in time and he wasn’t too tired, attend a dinner with the French ambassador. Back in Washington.