Daniela Brighenti

Jake Sullivan ’98 LAW ’03 is Hillary Clinton’s LAW ’73 top foreign policy advisor, a senior advisor to the U.S. government for the Iran nuclear negotiations and a visiting professor at Yale Law School. After graduating from Yale (and serving as editor-in-chief for the News), he attended Yale Law School and clerked for Judge Guido Calabresi ’53 LAW ’58 and Justice Stephen Breyer. In 2008, he advised for Hillary Clinton’s primary campaign before working for Barack Obama in the general election and ultimately advising in the Obama administrations. He left in 2014 to return to Yale Law School, and was married in New Haven in June 2015. Sullivan took a 20-minute pause from his extraordinarily busy day to chat with WKND.

Q: How did you get your start in politics, and is that the career you envisioned?

A: I always thought I’d be involved in some form of politics, whether supporting local congressmen or maybe one day working in Washington, but I never really had a clearly defined sense of what that would look like. My first political job was interning for Rep. Martin Sabo, from the sixth district of Minnesota, where I grew up. And I did that while I was at Yale — I spent a summer back in Minneapolis, interning for him. When I was in law school at Yale, [I worked] on Paul Wellstone’s re-election campaign for the Senate in 2002. That was the campaign where, shortly before the election, he died tragically in a plane crash. And then in 2006, I ended up back in Minnesota again, working for Amy Klobuchar, who was running for Senate. [I was] just helping her out, mostly informally — I spent just a few weeks on the campaign full-time. But when she won in 2006, she asked me to come out to Washington with her, to help get her office up and running and help manage her transition into the Senate. I did that at the end of 2006 and into 2007, at which point I got an opportunity to go work on Hillary’s 2008 presidential campaign. I guess the rest has unfolded from there.

Q: What does a typical week look like for you, with the campaign in full swing?

A: I have a totally unpredictable schedule. It changes hour-to-hour and certainly day-to-day, but it involves a mix of being in Brooklyn — which is where the campaign headquarters are and where I manage the policy team — to being on the road with the candidate. I’ve traveled with her to some of the early states, and I’ve traveled to more than a dozen states just on my own, representing the campaign in one capacity or another. So some combination of those three things, but it means a lot of time living out of a suitcase.

Q: How do you balance all those roles — what’s the secret?

A: I think the most important thing is to just maintain transparency and open communication with all of the people I deal with on the campaign, without regard for hierarchy, without regard for who holds what position. The more information you provide and seek, the more capable you are of making a positive impact. It really is about trying to engage with people across the entire operation.

Q: What is the biggest difference between policy work for a campaign and the type of policy work that happens within government?

A: I’d say the single biggest difference is that when you work in government, you’re not merely advocating a position; you’re executing decisions, you’re putting policy into practice in the real world and it ends up having real impact on real people. That is the most rewarding kind of work, and it’s also very high stakes work. People depend upon your good decision-making. In a campaign, it’s more about arguing for a position, advocating for a position, staking out a set of principles, a set of policy ideas. But it’s not until you’re elected that you actually have the opportunity to go ahead and implement them and see what works and what doesn’t, make adjustments, learn from mistakes and build from successes.

Q: Do you have a particular theory or particular principles that guide your policymaking?

A: Well, it really depends. In the foreign policy space, my core principle is that the fundamental project of American foreign policy over the next two decades is to secure and sustain American global leadership, because I deeply believe that a world America leads is a world where everybody ends up better off. Certainly where U.S. interests and values are protected, but where the interests and values of our friends and of people across the world are also protected. For me, that’s the cornerstone — what’s it going to take to ensure that the United States maintains a leadership position in global affairs, even as the world changes around us? On the domestic side, I think the fundamental question — the touchstone of everything — is whether a policy is going to contribute to strengthening the middle class or to hollowing out the middle class. That is the question that I ask about any domestic policy issue.

Q: What do you think is the biggest misconception about working in policy?

A: That’s a good question. I think the biggest misconception is that there are clear right or wrong answers on policy. Many times in policy — especially in foreign policy — the choice is [among] a series of imperfect options. And any option you select is going to have weaknesses and blind spots and warts, and your critics are going to have some good points to make. What I worry about, with the nature of the political debate today, is that people shout at each other and say, “You’re an idiot for having proposed that policy, can’t you see it’s got these shortcomings?”

But I think a fair assessment of most policy choices, particularly in national security, is that there is no such thing as the ideal or the perfect policy choice. We have to live in a world where we embrace and execute policies that are just in their nature imperfect. If people understood that better, I think there would be more civility and more common sense in our decision-making and our debate, but unfortunately the filter through which most people experience and see policy, both on the campaign trail and in government, has become highly polarized.

Q: How do personal interactions help shape big policy decisions?

A: It’s interesting — one thing a campaign affords a candidate or their staff, that governing doesn’t quite as much, is more opportunities to be out there meeting with and hearing the stories of people who are experiencing challenges in their lives and looking for help. The Secretary, from very early on in this campaign, has had the opportunity to hear from people who say, “My family and my community are being ravaged by the epidemic of substance abuse,” or, “I used to have to pay a handful of dollars for my prescription drug, but now I have to pay thousands, if not tens of thousands, of dollars for those same drugs.” Down the line, being able to hear people’s stories and put a face to the policy challenges that we’re grappling with — it makes a big difference. It takes it out of statistics and white papers, and that’s incredibly important for us to remember. It’s easy for us to lose sight of that in Washington, but in a campaign, we have the constant reminder that this really matters.

Q: What do you think is the biggest challenge in the campaign?

A: The biggest challenge in any campaign, and particularly this year’s, is to be able to cut through the enormous amount of noise generated around the presidential campaign and really try to have a substantive debate about the issues and what it’s going to take to make sure that this country and its people can truly succeed. The biggest challenge I see on the campaign — and of course, I’m biased as the policy guy — is the difficulty of pushing through the cable and social media chatter to try to engage with the American people in a serious conversation about real issues that impact their lives and the future of this country. We obviously haven’t cracked the code on that. But there have been moments when the Secretary has been able to break through on policy, and those have been some of the most gratifying moments for the campaign, from my perspective.

Q: What is it like to know big political actors personally and to be on the inside in that way?

A: Having dealt with a lot of significant public figures, the thing that gets lost and stripped away in the coverage of them is that they are real human beings. I know that sounds a little bit cheesy, but these are people with strengths and weaknesses who have to grapple with hard decisions every day, whether you’re talking about someone in government or someone running for political office. And I have found, by and large, both with the people I’ve worked directly for but also many people whom I’ve had to spar with over issues like the Iran Nuclear Deal or whatever it may be, people are really just trying to do the best they can for the things that they believe in.

And the caricatures that emerge around people — not just the people I’ve worked for but for others too — [are] really unfortunate. There’s been a corrosive aspect to our politics that ends up demeaning us all. If people got a chance to really interact with someone like Hillary Clinton or Joe Biden or Barack Obama or Amy Klobuchar in the way that I’ve had the opportunity to do, I am confident that they would come to see just what extraordinary people each of them are, and the same would hold true for many people on the other side of the aisle as well. You make your careers in American politics these days much more by your capacity to take someone down than to build them up. I think we should collectively as a national community be pushing back against that.