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2015-2016 Issue II Editors' Picks Election 2016 Interviews National

The Negotiator: The Politic’s Exclusive Sit-Down with Jake Sullivan, Hillary’s Top Foreign Policy Advisor

I’m sitting in a coffee shop interviewing an up-and-coming political rock star. Between questions I make a joke about his not having had to prepare for our interview, because it’s just for a student publication.

Without hesitation he replies, “In the age of the internet, there is no such thing anymore as a more or less prominent publication.”

It’s exactly this type of constant awareness that has helped him achieve so much. Even getting in touch with him to set up the interview was remarkably painless. He clearly believes in political accessibility, but part of me wonders if this strategy ensures that the interviewer likes him before they have even met.

His name is Jake Sullivan. He is the former National Security Advisor to Vice President Joe Biden, former Deputy Chief of Staff to Hillary Clinton during her tenure as Secretary of State, and now one of the top foreign policy advisors on her presidential campaign. He rose to international prominence as one of the orchestrators of the 2015 Joint Comprehensive Plan of Action, better known as the Iran Nuclear Deal. He also happens to be a visiting lecturer at Yale Law School and currently lives in New Haven while commuting to Clinton headquarters in Brooklyn four times a week.  If you haven’t heard of him yet, you willsoon.

But for now, sitting in the coffee shop, Sullivan remains completely unrecognized. The Politic is getting in early, as this is the first time Sullivan has ever agreed to be interviewed for a profile. He previously turned down Politico and the New York Times. He told me that he was making an exception out of solidarity with student publications, having been an editor-in-chief of the Yale Daily News.

Jake Sullivan never planned on having a career in national politics.

In his own words, “I first got involved in national politics by getting involved in local politics. I moved home to Minnesota after my clerkships, planning to build a career there and to contribute to the community and to be engaged locally.”

He didn’t stay local for long. He served as chief counsel to Amy Klobuchar during her 2007 Senate campaign. When she won, he moved to Washington, D.C., for a few months to help her transition and set up her office. The move was supposed to be temporary. However, a mentor of his recommended that he interview for a position as a policy advisor for Clinton’s 2008 campaign.  He clearly made an impression: she has retained him as an advisor ever since.

Talking to Sullivan, one could get the impression that he just happened to be in the right places in the right times. This seems less like a politician’s false modesty and more like a genuine, deeply ingrained humility. There is sincerity in his manner that written quotes just can’t communicate.

When I ask him about his overall political views he explains, “I don’t think that being a lifelong Democrat means being hyper-partisan.” Even though he clerked for liberal Supreme Court Justice Stephen Breyer, he interacted with many staffers from the conservative wing of the court. He feels that this has given him a well-rounded view of politics.

Next I ask whether or not he diverges from the Democratic Party on any key issues.

He responds, “The party itself is a pretty big tent. You can stack up five Democrats and have a pretty wide spectrum of views from Joe Manchin of West Virginia to Bernie Sanders of Vermont, and everything in between. So I don’t think there’s an issue on which I would say there’s a consensus in the Democratic Party and I deviate from it.” His tone is so convincing that I simply write down that his view of the party is comprehensive. It’s only later, reviewing my transcript of the interview, that I realize he may have dodged the question.

It’s not hard to see why he has been chosen as a key figure in not one, but two major campaigns, and why more experienced politicians keep placing their trust in him. As a campaigner, he’s always on. I ask about Donald Trump and cultural extremism, which he immediately steers into praise for Hillary and how she moves beyond empty rhetoric. While reading that may set off your cynic alarms, in the moment, I never for a second doubted his sincerity.  In Sullivan’s reasoning, when you bring up poison (Trump), of course you’re going to talk about an antidote (Clinton). Once again, it’s only later that I realize it might have been a calculated move.

Sullivan says he’s nonpartisan, and works hard to keep his career as an educator from reflecting any political agenda. As an academic, his area of focus is 21st century politics. He is quick to acknowledge the potential for biased pedagogy given his close proximity to what he teaches. To avoid this, his class on current foreign policy is jointly taught with two other professors. He even included a reading that was a “full frontal assault on the [Iran] Deal.”

On his attempts to be completely nonpartisan in the classroom he adds, “Any argument you’re going to make will have weaknesses and blind spots and you should acknowledge them. Any criticism is going to have some kernel of validity, and you have to acknowledge that too.”

We next delve into the negotiations that have secured him a place in the history books: the Iran nuclear deal. The agreement was signed in July 2015 after several months of secret meetings. The goal was to drastically reduce Iran’s nuclear capabilities. However, it has faced criticism for not being tough enough and for relying too heavily on faith that Iran will stick to the rules.

Sullivan first became involved in 2012, participating in secret face-to-face meetings with Iranian officials in Oman. After a few months, a delegation formed to carry out more secret meetings to create an interim deal. This ultimately led to the Joint Comprehensive Plan of Action.

Sullivan does not have any delusions that the deal is enough on its own. It is odd to hear a political figure deliberately downplaying arguably his crowning achievement, but with characteristic modesty he tells me, “It is not enough just to say, ‘Okay, we’ve got the deal.’ The deal needs to be enforced directly, aggressively and vigilantly and embedded in a broader strategy that pushes back against Iran.”

He adds that Clinton will be an excellent future negotiator, citing her track record on Iran: “She is exactly the kind of person who can rally the world to ensure that Iran complies with the deal.” Once again, he steered the conversation toward Clinton’s presidential abilities so organically I didn’t notice the plug until I was reviewing my recordings.

My next question is whether or not he sees any major potential for failure in the deal.

“Actually, Secretary Clinton gave a big speech at Brookings in September that I helped her think through but that she very much put her stamp on, and which I encourage you to read,” he responds. “It actually walks though, in very plain language, what she sees as being the main challenges. One is that Iran cheats. Another is that Iran waits us out until the end of a 15 year period of significant nuclear constraints, and one is that Iran uses the deal as green light to engage in all kinds of problematic behavior in the region.” However, Sullivan believes in the ability of the United States and the United Nations to enforce stricter terms.

“That is going to require a comprehensive American strategy using all the tools at our disposal, working closely with our allies and partners, and sending a clear message to Iran right from the start,” he says. “There will be consequences–if you cheat, we will not let you wait us out, and we’re going to be there at every turn checking on your efforts to engage in. negative behavior in the region.”

Our conversation is wrapping up, and now I throw in some get-to-know-you questions. Sullivan reads all kinds of newspapers and political blogs, but doesn’t watch television news because it’s not illuminating and too time-consuming. He loved his time at Yale (both as an undergraduate and a law student), and his best friends from college are still among his closest and even spoke at his wedding this summer (in Battell Chapel, no less). He calls Harry Truman his political hero and considers himself a “Truman Democrat.”

The most interesting answer comes when I ask what his favorite books are. He immediately replies Pride and Prejudice and The Great Gatsby. This surprises me because they’re novels, and both unapologetically romantic. He did not choose a nonfiction book or a political manual or a Russian epic (Clinton’s favorite novel is Dostoevsky’s The Brothers Karamazov). He chose two books that are about love and passion and dreams. Maybe this is why he truly doesn’t seem like a politician, even though he is heavily involved in their world.

I ask him if he has any final thoughts he’d like to share, and he mentions something he had said earlier: “Policymaking is a study of imperfections.”

He wants people to understand that, in his own words, “When we learn about government, we learn about institutions and interests; we don’t learn as much about the fact that no institution can be more than the sum total of the human beings that comprise it.”

The next day I attend a Master’s Tea hosted by Jonathan Edwards College, at which he is the special guest. The house is packed, one of the most well attended Teas I’ve ever been to. I end up sitting on the floor in the back. He starts talking and doesn’t sound particularly different than he did the day before. Still, his presence seems to have somehow been dialed up to fill the room. Talking about his early history, he leaves it to Master Penelope Laurens, the interviewer, to tell the audience about his Rhodes Scholarship and academic achievements, all of which he never once mentioned when I interviewed him.

One story in particular captivates the audience. He describes a group of heads-of-state leaving a meeting in Copenhagen at 3:00am. There was a blizzard outside, so they end up having to wait while their motorcades pull up one at time, forming “the world’s weirdest taxicab line.”

After 15 minutes of waiting, Nicolas Sarkozy, in the middle of the line, looked up at the sky and shouted in English, “I want to die!” The other heads of states immediately burst into applause. This is indicative of many of the stories to come: funny, relatable, interesting, but ultimately not very revealing.

In front of a crowd, he seemed equally as comfortable speechifying as he was in our one-on-one talk (although his wording was no less colloquial). He even responds to a few aggressively worded “gotcha questions” with total cool-headedness. The content of what’s being communicated is pure political speech, but the tone is so confidential, so easy to like, that you forget to be skeptical.

As the Tea ends, I begin to walk over to him to thank him again for agreeing to be profiled, but a bit of a crowd surrounds him. I can’t hear what he’s saying from across the room, but I can see that every listener’s face is rapt. This is the man who helped convince Iran to give up most of its nuclear capability; I guess I shouldn’t be surprised that people like him so much. He plugs his boss’s agenda and campaign, but he does it so naturally and charismatically you forget to ask yourself whether it’s all a performance. Maybe Sullivan is the only one who really knows the answer to that question.  Still, when so much of politics is performance, that blurring of lines might be his greatest asset.

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