Joel Benenson is the founder and CEO of the Benenson Strategy Group, where he has served as a consultant and strategist to various political leaders, Fortune 100 CEOs, and community leaders. Benenson was also the chief pollster and senior strategist in the 2008 and 2012 Obama presidential campaigns, and most recently, in 2016, he was the chief strategist for the Hillary Clinton presidential campaign.

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The Politic: You’ve been a pollster for many candidates across the country. Which have been the campaigns that you were the most excited to work for?

Benenson: Well, I think the one that was a once in a lifetime opportunity was President Obama’s first election, and I was brought in very early by David Axelrod, who’s like my brother from another mother. And I had been nagging him all through the fall of 2006, and every time we spoke he would say, “Just sit tight, just sit tight,” and then finally, when we were ready to go, which was before the first of the year, he then called me and said, “Okay, we’re going.” I think that everything about that campaign from beginning to end—the culture, the historic nature of it—was secondary; it was just an unbelievable team effort, and he was an extraordinary candidate. He was a once in a lifetime candidate, and I still love the guy.

He is pretty amazing, I would agree. Going off of that, what do you think would define a successful campaign?

I’ve worked on a lot of campaigns, and I think what was unique about this campaign—and I think it emanated from President Obama, then Senator Obama—when David Axelrod put the team together, and everyone on the campaign knew what their role was, and they knew that they were going to be trusted to do what they were tasked to do in their role, and they also knew that if they were needed outside of their lane, they would be asked.

There wasn’t a lot of jockeying for position because that was not tolerated. You stayed in your lane, and that was the culture. And it was mutual respect, a lot of trust, and not a lot of backstabbing and jockeying for position that goes on a lot of campaigns, and I think that emanated from the top. I think that is how President Obama functions. He trusts people that he trusts, and he will call on you when he needs you, and that filtered all the way down through David Plouffe and Axelrod. Everybody on the campaign knew that was not only how they were going to operate, but that is how you would operate.

Moving on a little bit, what does a typical day in your profession look like?

Now or then?

Talking a little bit about both—then and now?

Well, I run a company with about 50-60 people, and I am the CEO, but in the context of being a pollster in a campaign, that’s probably a little bit more interesting. I think when a campaign—well, look, we bring a unique perspective because we have a lot of expertise in language, and a lot of the people that we have hired at my firm are former journalists, former writers, people who made TV ads.

We don’t look for people who are classically trained as pollsters because what we want to do is marry the art and the science of polling to help inform messages that work. So, our job is a little different, and I think that any day could be a different challenge, but we spend our time thinking about the right questions to ask to uncover what is really going on beneath the surface of whatever challenge or issue that we are working on for whatever client. Because that’s when you figure out what the attitudes or values are of the people who are in your target audience, how those attitudes and values are shaping their decision frame. That is when you really start creating communications that can connect with them more deeply, and that is powerful. And that is what we spend a lot of time doing. Obviously, we have to do our work, which we conduct with both qualitative and quantitative research, but we are high level strategists particularly with an expertise in messaging and also getting beneath the surface to what we call “uncovering the hidden architecture of opinion.”

And moving to a bit more recently, why did you decide to take on the role of chief strategist of Hillary Clinton’s 2016 campaign?

[Laughs.] Well, that’s an interesting question, and the role morphed during the course of the campaign, but we didn’t know each other well, and I really thought it was going to be an important election to try to preserve a lot of what President Obama had done. And I didn’t think I would work on another presidential campaign after 2012, and I didn’t know Hillary before we met. Several people said that she wanted to meet with me, and then she reached out and asked to meet with me. Then we hit it off, and I thought if I could—even if I was disinclined to get involved in another one—I thought that if I could do something to make sure that we elected a Democratic president [I] should do that, because I thought that the country was still not out of the woods. And history has proved me right, we are still not out of the woods, it just did not turn out the way I thought it would, that we would be able to elect the Democrat, Hillary. With that being said, it was a tough campaign though for a lot of reasons.

Expanding on some of those reasons, what do you think were some of the biggest roadblocks that you faced during that campaign?

Oh look, I think we found out the morning after she gave a speech at the Emily’s Center about the emails. For some of us, we found out, myself included, when we read it in The New York Times that morning. And that was just a problem that we were never able to navigate around. The press was relentless on it. The story, like a cat, had nine lives, and you would think from time to time that we got past it, and then it would crop up again, even the Comey announcement—which was 11 days before the election, which was totally inappropriate, he had no evidence of anything, and it just reinjected it back into the bloodstream. In fact, even on the Sunday or Monday he said that there was nothing to it, right before the election. I think I was one of the only people that said that this was a problem for us. We are a week out from the election, and he has just put the emails back into the conversation again. And anytime the emails were back in the conversation, it was a bad day for our campaign.

Do you think that other than the emails, Donald Trump’s campaign did things that allowed for a victory for him?

No. Look, they all thought that they were losing on Election Day. They deny it now, but they told every reporter under the sun that they were all looking for jobs, every one of them thought that they were losing on Election Day. I think that there were things that we didn’t do that I think we should’ve done, and I think that losing three states that had been part of the blue wall in the Electoral College, Pennsylvania, Michigan, and Wisconsin, is unforgivable.

Everything had to emanate from winning the states that were in our blue wall, that got us to—I believe it was about 252 electoral votes. Because winning each of those states meant that we had so many more ways to win than a Republican did. And that has to be the starting point of everything you do, and you can never take any of those states for granted, and when you lose across those three states by 88,000 votes, and some 600,000 people across those three states voted for the third party candidate, basically threw their vote away or helped hand the election to Donald Trump—I think that anybody on the campaign should be thinking about how we let that happen and how we couldn’t find 85,000 or 90,000 people from those 600,000 and stop them from voting third party and vote for Hillary. And I don’t think that we had an aggressive enough effort to do that, because you win those three states and Hillary Clinton is president.

On that day, did you think that you were going to win the election?

I did. I thought that—you know, it’s funny, I thought that we would win, I thought that it was going to be close. Some people thought it was going to be a blowout, polls were all over the place, [but] I thought that at best, we were going to win the four-point race.

Our electoral strategy obviously [appeared] better than it turned out to be, our electoral votes strategy. I will tell you this: on Election Day, the night before Election Day 2012, I think Dan Pfeiffer sent me an email and said, “What’s your final prediction?” and I went through the numbers, and I sent the team back—Dan was asking, it was a group email—and I think I sent back the numbers that it was 51-47, even with a decimal point maybe, and we won 51-47. And, sitting in a room of what was Hillary’s old office at one point on Election Day, I kept trying to come up with what the final vote number was going to be. Even though we concentrated on the battleground states, [I was trying to find a number] that translated well nationally, and I couldn’t come up with a number. And I kept trying to figure out what the third party numbers were going to be—would it give us a four-point win, a five-point win—and I still thought we were going to win, but I couldn’t get to a number. And in both 2008 and in 2012, I was able to get to a number, and I was pretty spot on both times. And that troubled me, that was the only thing that troubled me during the day, but I still didn’t see a path for Trump getting to the electoral votes he needed based on what we were hearing.

I was a little worried based on the information we were getting by mid-afternoon; some of the political professionals that worked in Florida were hearing very worrisome things out of Florida while some [other] people weren’t getting as dire word as we were getting from some of those states. So, it was a day where I thought we were going to win, but at some point, in mid- to late afternoon, there were troubling signs. Then at some point, we knew we were going to have problems. And in the evening, at one point when our analytics people or our field people started saying, “Well, you know, if we win, we are still going to have New Hampshire,” some communication came through where we all looked at each other and said that this thing is going south.

What advice would you give to students who are aspiring to work in political journalism, politics, or polls?

You covered quite a bit there. I think I would say, do a little bit of everything. It’s a big field. There are more and more specializations that are occurring, and to figure out where your right place is, work on a campaign somewhere, go out on the field, knock on doors, talk to real voters, understand what it’s like to communicate with voters one-on-one. I remember one of the most exhilarating experiences on the Obama campaign was in the summer of 2007, David Axelrod and I went up to New Hampshire and did a whole briefing for the field people in some beautiful location. And it was just great to hear from them—they were already talking to people—what were they hearing from people. Get that experience as well. Don’t just try to rise to the top.

If you are a political journalist, stop chasing the story of the day, if that’s what you want to do. Find something more interesting than the horse race because the horse race, it’s the least important number in a poll most of the time, because the other data is going to inform you thinking of a new strategy. So, ask the questions you think nobody else is asking. Whatever you are doing in politics, always ask the questions you think no one else is asking.

And do you believe in the future of politics? Do you think, the country will move, in your belief, in the right direction?

Well, look, history would say that we would. We may be in slightly uncharted waters, but we have been in uncharted waters before, rarely because of a president who is so uninformed, lacking in humility, [and has a] complete lack of understanding in the rule of law and the history of this country. And that is posing challenges for everybody involved. This is a pretty resilient country, and there are some dangerous things happening that we haven’t seen before, particularly with the extreme right wing—providing aid and comfort to white supremacists out of the mouth of the person in the White House.

Those are kind of unusual circumstances, certainly not what we would expect first half of the 21st century, but you know, the democracy was built around a system of checks and balances, separation of powers in reaction to a centrally powerful, singular monarch, and that was done to put restraints on what that centralized power could do. It would be a lot better if Congress, if the Republicans in Congress in particular right now would strengthen their spine and would take on—some do—the most egregious abuses that are coming out of the White House and the presidency now instead of remaining complicit through their silence, which I think they do too often. That is worrisome, maybe they will be jolted—the numbers today are that 36 red seats have been turned to blue in special elections since Trump was elected—but I think I still have faith in the democracy, and it is being tested in a way that it never has before.