Kyle O’Connor Oral History

This is the Kyle O’Connor interview for the Barack Obama presidential oral history. We do a whole life, so we start at the very beginning. Where do you come from?

I grew up in beautiful Herndon, Virginia, a couple of hours north of here. My dad was a teacher at our public high school. My mom stayed home for 15 years. I have two brothers, so she stayed home with us and went back to work part time.

What are you in the birth order?

I’m the oldest. It was a fun upbringing. We didn’t have a ton of exposure to politics. My parents both voted a lot but didn’t volunteer in campaigns. It wasn’t a big thing. We were near D.C., and it was always fun to go into the city. We went on a bunch of field trips in school. It was a fun time and place to grow up.

You said they were active voters. Did they have a party they tended to support?

Yes, they were Democratic voters consistently. This was at a time, as you remember, when Virginia was very much a purple state—it was more red at that point, and so it wasn’t the way it is today. My dad took me to [William] Bill Clinton’s first inauguration, or maybe the second. So I caught the bug, but we didn’t have these “Rahm Emanuel family discussions” around the dinner table [laughter] or fighting about every issue of the day.

Why do you think they were Democrats?

That’s a good question. My dad’s parents—my grandmother was a Democrat, grandfather was a Republican. They said they would just cancel each other out.

Were they from Northern Virginia too?

They were in D.C. That’s a good question. I hadn’t really asked them that. As a public school teacher, I think my dad was more conscious of the value of that and wanted to vote for a government that would support public schools. I don’t know. I think that’s how they grew up.

Tell us about your impressions as a young child and student of the 1993, or was it the second inaugural, did you say?

It might’ve been the second.

Did it feature an impenetrable poem by Maya Angelou? [laughter]

You know what? We staked out the parade route, and so I don’t think I even heard it. As a kid, I’m sure that would’ve gone straight over my head.

It was about rocks and trees and things, but beyond that I can’t say much.

That doesn’t stick in my mind. But we were on the parade route, and I remember seeing the Secret Service and feeling like this was a big, important thing. The only thing I do remember is they have the President on the one side of the limo and the First Lady on the other side when they do the trip down the road, and we were on Hillary Clinton’s side. So I was all excited to see the President, and then we saw Hillary. In retrospect, also a big deal, but at the time I was like, Aw, I didn’t even see President Clinton. But, yes, being close to D.C., I felt like we were close to something big that was happening.

You said that was the first time you recognized that the political bug might have bitten you. How did that play out in what you were writing on or studying in school and then taking you through up to college?

The other thing that I remember was President Clinton came and spoke at my elementary school. It was a speech on education. I was in middle school at the time, I think, but my brother was the treasurer of the class, and so he got to invite a guest, and he invited me. Now, looking back, we staged another school, and then moved over, and I remember being amazed at that. I got to shake his hand at the end, and then I got interviewed by the local news. They asked me what I thought about Bill Clinton. It was right after the Monica Lewinsky stuff, and I think I said, “Well, he doesn’t seem to tell the truth a lot.” [laughter] And, of course, that’s the clip—and I was mortified because I actually liked him as a kid, and that was the thing that was on the news. There’s a VHS tape somewhere that my parents have.

As I went into high school, I started to become more interested in politics. There was a political science class that was well known in my high school. There was a teacher named Doug Graney, and because we were so close to D.C., he had this arrangement where, for the first half of the year, you’d learn about politics and political science in the class. And then for the second half of the year, he would get all his students internships on the Hill. We were high schoolers. We could barely drive. He was like a bulldog, where he would just call these offices and pester them until they agreed to have—It was an unpaid internship, so it wasn’t that much of a problem for them.

We loved getting off school early, so that was part of the appeal. But then we would drive downtown. We’d carpool and work in these offices. He would always really drill into us, “Don’t screw this up, because I need to be able to put another intern in this office next year, and if you mess it up, then they’re not going to want us to send anybody else.”

So I interned in [Edward M.] Ted Kennedy’s office, which I was really, really excited about. My mom was from Massachusetts, so there was the connection there. This was toward the end of his career. I think I was so starstruck by being on Capitol Hill as a high schooler that I didn’t pay enough attention to the policy stuff that was going on, but I knew that I liked him.

It was my first exposure to what it was actually like inside the political system. After that, I was hooked, so went to UVA [University of Virginia].

Did you get to meet the senator while you were interning?

I met him once, maybe, for the picture that he took. I did a lot of work in the mailroom, a lot of work running errands for people. I gave a couple of tours. I walked the dogs.

Oh, Sunny and Splash.

Yes, yes. [laughter] I remember going out with another intern, and they were famous at the time. And we were like, Well, we can’t lose them. We can’t let them run into traffic. This is on us. So, yes, it was terrifying and fun. They knew their way around better than we did. We just kind of followed them.

The other thing was our teacher didn’t tell us what to do about parking, so we would park wherever we could on Capitol Hill. I think I got a couple hundred dollars’ worth of parking tickets by the end of that semester, but it was worth it. It was a really cool time to get in there at a point where most people didn’t. All the other interns would go out for a drink after work, and I would go back home to my parents’ house.

Do your homework.

But I give Mr. Graney all kinds of credit for really pushing to give kids that experience because, for people like me, it was the beginning of a lifelong love of this stuff.

Oh, that’s wonderful. Russell, do you have anything at this point?

Why [University of] Virginia?

My parents were not the most well-off people in the world. As a public school teacher, they did a great job saving for us for college, but the deal was, if we went to an in-state school—and part of the reason they moved to Virginia was because there were really good in-state schools—they would pay for it. If it was an out-of-state school, like my brother went to Notre Dame. He had to come up with the rest in scholarships and other things like that.

I applied to three Virginia schools and three schools outside Virginia. I don’t think I got into any of the schools outside Virginia, so I thought, OK, well, this is my choice. And UVA was by far the best place. None of my family had gone there, but I visited. And just being from Northern Virginia, there were a lot of kids—25, I think—from my high school came to UVA the year I went. I didn’t love that at the beginning because I was thinking, Oh, it’s just going to be like high school again. But then you get down here, and you realize there are a lot of people here, and you don’t have to see everybody from your school if you don’t want to. It just seemed like a great combination. I wanted a school with sports and a school with good academics and connection to history and politics, and UVA had it.

Were you, even at this young age, since you had been bitten by the politics bug, thinking that at some point you might run for office?

No. I was and still am kind of shy, and so I didn’t think that I would be the one asking for money or going up there and asking people to vote for me. I remember hearing somebody say, “You can be the person, or you can be the person that person can count on.” And I always pictured myself as more of the behind-the-scenes person, somebody who was involved but not the face of it. Just my personality, I think, was more suited for that.

But also I think I was probably a little afraid of failure. A lot of being an elected official is, you put yourself out there. And if people reject you, then that’s it. I think that would’ve been tough for me and would probably still be tough for me. But luckily, that fits with speechwriting and what speechwriters end up doing.

Did you know coming in what you wanted to major in?

I didn’t. I thought there was a chance I would go to law school, but when I got to UVA, I found that I really liked politics, and I also really liked sports and sportswriting. Besides working at the Miller Center, I had two other activities in college. One, I was a volunteer firefighter in Charlottesville [Virginia], which was fun. One of my good friends had been doing it since high school and got involved here. And then the other was as a sportswriter for the Cav [Cavalier] Daily. So, I ended up covering some teams. I did a season with the volleyball team. I did some lacrosse, a little bit of football. I ended up getting a column in the paper, so that was great because you could write about whatever you wanted.

That was actually some of the best training for speechwriting, because I’d have to go out and find something interesting or something I cared about and make an argument in 400 words for why somebody else would care about it. I loved it, and I thought there was a chance that I’d want to be a sportswriter. But then I covered—I think the lacrosse team was in the national championship. It was my first time in a real press box, and so I went up to Philadelphia to cover that game. I looked around at the other people there, and everybody looked like they weren’t having a great time. [laughter] Everybody was just tired, and the food wasn’t good, and these long days. And I’m thinking, I don’t know if I want this to be my life.

So I thought about, is there a way to mix the two things I liked, which is politics and writing, and thought of speechwriting as a way to do that. Well, the first summer out of college, I worked on the runway at Dulles Airport. There was an airline called Independence Air that is now bankrupt, but they were hiring college kids to basically work on the runway and throw the bags and move the planes.

What about fly the planes?

No, but we shouldn’t have even been doing the other stuff. They gave us two weeks of training and then sent us out. That was the first summer.

Then I was looking for an internship at a political consulting firm. I went down a list of all the firms I could find and emailed everybody, heard back from two. One was Squier Knapp Dunn, SKDK. At the time, they were 15 people, and they called me and said, Hey, we’d love to have you on as an intern. We’ll pay you a whopping $9 an hour, which for me as a college student was like, Great, I’ll be set for the next year. So for a couple of summers after my sophomore and junior years, I interned at SKDK.

Is that Bob Squier?

Bob Squier was one of the founding partners. Anita Dunn and Bill Knapp were the two that I worked with. That was fun because I’d seen the inside of a Senate office, and I got to see the inside of a firm that was working for multiple clients, and I got a little bit of experience doing everything. I did a little bit of speechwriting. I did a bunch of research. I did some odds and ends and commercial shoots, that kind of stuff, and really loved that.

So as I was getting that experience during the summer and writing for the Cav Daily during the year, when I was about to graduate I was thinking, OK, well, is there a way to mix these two in a job? At that point, I’d interviewed for a consulting job because that’s what my friends were doing. It seemed like those were the good jobs, and so I was like, OK, I’ll try and get one of those. I had an offer, but at the same time, Barack Obama was on his way up in the Democratic nomination fight.

What year would this have been?

This would’ve been the spring and summer of 2008. I graduated in May 2008. Meanwhile, Anita Dunn, who was the partner at the firm I worked for, was on the Obama campaign. I knew she was involved, and so I emailed her every couple of weeks. I had a mark on my calendar for every time to email her during the spring semester and just said, “Hey, I’ve got this job, but I’m not super excited about it. I’d love to get some experience with the speechwriters in Chicago at the Obama campaign.”

I’d read a feature on Jon Favreau, who was the head speechwriter for him. He just seemed like a really cool guy. So eventually, I got an email from Jon, whom Anita had passed my information on to. I think I’d finally broken her down. [laughter] He said, “Hey, I hear good things about you from Anita. We’re looking for an intern for the last six months of the campaign. We can’t pay you anything, but would you want to come out to Chicago?” I said, “Of course.” So I graduated in May and flew out to Chicago in June and joined the campaign.

Wow. So let me back up just a little bit. You had seen Hillary Clinton in the limousine. Was it because of the connection to Anita Dunn that you thought this makes sense to try to get into the Obama speechwriting shop that way? Or was it that you really were drawn to the Obama concept, Obama himself, the campaign? In other words, why not Hillary over Obama?

I remember at the time my friends at UVA were kind of split, those that were Democrats were split between who they were going to vote for. I remember Hillary came to UVA and spoke at Old Cabell [Hall], and I think I went to see her.

But Obama, to me—like a lot of other young people who were part of his coalition—seemed really different, really inspiring, amazing speaker, somebody you could believe would try and make politics a little bit different than it had been. So I think I was right in the wheelhouse of people who were excited about him. I don’t know. It just had a different feel, and I gravitated more towards him than her. It was a little bit of that.

I remember watching his race speech in Philadelphia live and just being blown away. And then the fact that I also had a connection to his campaign made me want to go that route.

Before we get too far from this, what about your familiarity here at UVA? You majored in politics, philosophy, and law?

Yes, it was PPL, political philosophy, policy, and law. You mean what kind of experience did I have?

Exactly. Were there academic influences on you at the time that are worth noting?

One was the Miller Center. I remember listening to the [Lyndon B.] Johnson and [Richard M.] Nixon tapes and feeling like I was a fly on the wall listening to something that I shouldn’t necessarily be listening to. [laughter]

Actually, when Lyndon Johnson would talk, you’d want to find a place to hide.

Right, exactly. I remember when Nixon was talking, you could hear a clink of a drink. And I remember talking to some of the scholars here, and they said he would crank up the heat—or no, he would light the fireplace and crank up the air conditioning to balance it out, and have a drink right there. And you’re just like, Whoa. And then start he’d calling whoever he could think of. I was like, This is crazy. But it was a more human side of history that I had never seen.

Then on the more practical side of politics, I took Professor [Larry J.] Sabato’s campaigns and elections class. We did a week on every piece of a campaign, so I got to see how you actually execute some of that stuff, including a week on speechwriting. That made me feel like I got a little bit of a sense of, OK, what would this look like for real? I got to see what it looked like when you get to the White House, the Miller Center, and also a little bit of how you get there, through the class.

Professor Sabato is still a friend. He identifies kids he thinks are into politics and might want to do it as a job and then does what he can to help them. I remember him being a really encouraging force in my life when I was trying to figure out what to do.

OK, thanks.

So, you’re in Chicago. Get us to Chicago, and what that’s like. This is what you had dreamed of doing. Tell us all about it.

Looking back, I had no idea what I was doing, like anybody straight out of college, and thought I did. I showed up. I was renting a room in an apartment from the brother of a friend. Meanwhile, I was quickly running out of money.

In college, you make enough money in the summer to last through the year and not much further than that. I was at the end of the year. I actually hadn’t turned it down yet, but I had postponed this paying job, and so I was running out of funds. My parents, I think, loaned me some money, which was nice. Of course, you don’t want to owe your parents anything, so I was thinking, As soon as I get a job, this is the first thing I’m paying back. But I was lucky that they could do that.

So I was living in Chicago. I remember walking into the Obama campaign headquarters as a 22-year-old, and it just felt like the center of the universe. You’ve probably gotten this from a lot of people you’ve talked to. But at the time, this was where everything was happening. The day before I started, I think, Hillary had conceded, or shortly before then.

Oh, right, that was in June of ’08.

Yes. So at the same time I was starting, a bunch of the Hillary staffers had joined the campaign. I think Patti Solis Doyle was there; Sarah Hurwitz, who was her speechwriter, joined; and a couple other people I’m forgetting. They were coming in the office at the same time I was.

And what was that like to have people coming from what was viewed as the enemy camp perhaps?

It was awkward for me because I didn’t know any of the background. This was, as you know, a really, really contentious primary. They got personal, and they didn’t like a lot of people over there. So as I was coming in, they were coming in, and everybody was sort of looking because it’s like these people you spent six months hating, who’ve been trying to take you down, all of a sudden they’re walking into your office.

Did they mistake you as one of the—

No. [laughter] I think they were like, This kid looks like he’s 16. I was trying to figure out what are the dynamics going on here. But to everyone’s credit, they seemed to get into it pretty easily and pretty quickly because all of a sudden you’ve got a new opponent you both don’t really like, “the enemy of my enemy is my friend” kind of thing. That was fun. It was nice to have new people who were also new with me, so I wasn’t the only one who was walking in there for the first time.

Right. Favreau, you said that you had read about him and he seemed interesting. Tell us about him and now working with him. And it’s still unpaid. How long did that go?

That went the entire time.

The entire campaign?

Yes, and it was six months, so I ran out of money. I think my parents had given me enough to have a little bit but not enough to pay the rent at a certain point, so I moved in with my aunt and uncle who happened to live in Chicago. I think I showed up at their door. [laughter]

With a suitcase.

And I was like, “Hey, do you mind if I stay here for three months?” They were nice enough to say yes. But at that point, a lot of people in Chicago had Obama staffers staying with them because you had people all over the country who had come through Chicago on their way to another state or who were doing time in headquarters after being out in the field. A lot of my aunt and uncle’s friends had Obama staffers staying with them too. It was like a supporter badge of honor to have somebody living in your basement.

But you asked about Favreau. He was this larger-than-life figure in my mind before I met him. And I don’t want to say this in a bad way, but I feel like a lot of speechwriters either fall into the camp of they’re completely anonymous or they’re stars in their own right. I would put myself in the first category, but he was in the second category. He was this funny, good-looking, charismatic, great writer guy, really young. I think, at the time, he was 26. He and a bunch of other staffers lived at this house called “the Pad,” and they would have parties there on the weekends. He was kind of this guy you wanted to be.

He was really generous to me at the beginning because they had had other interns, but I think he knew that I would be his intern through the duration. He gave me time. He answered my questions. He taught me a little bit about speechwriting. Although in my job as an intern, I wasn’t doing much writing. I was doing research mostly.

The President, at that point during the campaign, was doing an event every day at least, sometimes multiple events. So a lot of the time, he would be doing the same stump at each stop. They would refresh it once in a while, but my job was to figure out the local color and figure out, OK, where is he going to be? What are a couple of things he can say that the audience will identify with that will let them know he’s done his homework a little bit? Little by little, they would give me little things to write. Maybe it was a quote that was going to go somewhere in print.

The first thing I ever wrote was a one-minute-long birthday video for Senator Neil Abercrombie from Hawaii. I thought that was the coolest thing in the world. He would do these taping times, and now I know how those go: you just record a million things at once. But I wrote my little one-minute thing, and he recorded it. Then I got to see him speak something that I wrote on video. I sent it to everybody. [laughter] I sent it back home and I was like, “Hey, I’m doing something.”

That’s important because he’s from Hawaii, right? If you’re off, he will know that you’re off in some way.

I felt like the weight of the world was on me. I’m sure they were like, “Yes, let’s just give this to Kyle.” That was the first time I’d ever written anything that somebody else had read, the first time I’d ever written anything like a speech, which is weird because I was interning with this amazing speechwriting team. That was another thing where I remember it as a moment my life kind of changed, like, Wow, this feels pretty cool, and I want to do more of this.

What are you learning about speechwriting and how those shops work? Was it anything like what you had learned in the Sabato class in the week on speechwriting for campaigns?

It was not much like that. It was like that in the sense that the content was similar. But seeing how speechwriting was done on a presidential campaign was eye-opening to say the least, just the volume of stuff that was happening. They had a whiteboard on the wall that was a big calendar, and then on every day they had written in what the speaking events were. Every day was taken up. At that point, I think it was Jon Favreau, Adam Frankel, Ben Rhodes, Cody Keenan, and Sarah Hurwitz, who was the Hillary speechwriter. That was it.

They were all doing two or three things at once. The pace was nuts, and they were all crammed into one little office. I’ve got a picture if you want to see it. You don’t have the luxury of going off and writing by yourself unless you want to go to the coffee shop or something. Everybody was just jammed in there. Everybody had their headphones on, and the pace was just nuts. It was more nuts than it was in the White House, and, obviously, the stakes were lower than when you’re President. But I think at multiple points, Jon and some of the other writers almost burned out. But that’s when they were bringing one more person and kept going.

I was amazed at the quality that they could churn out on a constant basis, and they weren’t talking to Obama that much. Adam Frankel, who was involved in a lot of the early speeches, said that for New Hampshire, where he [Obama] lost, they basically kept the speech. He just changed the first line to acknowledge that Hillary won. I didn’t realize this until recently, but Obama had not seen that speech until, I think, the day before. That became the “Yes We Can” speech that would take off and become part of a lot of other things.

Was that common that they had to just write so quickly, and it was like a creative assembly line where you had to keep writing, writing, writing because he was doing things every day? And was it typical of him not to be able to spend much time on each speech?

I didn’t have first-hand experience on this, but what I’ve heard is that, yes, he was on the road. He was doing in-person events. He was really busy. And for big speeches, like for the race speech, he called Jon Favreau and said, “I’ve been thinking about doing this for a while. Here’s what I want to say,” and basically dictated a majority of that speech.

I think Favreau would call him, and he would get calls from him once in a while for bigger things, but he just didn’t have enough time to really spend on the speechwriting. I didn’t realize that a lot of the speechwriters were freelancing and doing what they thought he should say but didn’t have a lot of guidance up front, which must’ve been really tough.

Did he have a traveling speechwriter? Did he have somebody on the road with him?

Sometimes one of our writers would go on the road but not that often. He didn’t have somebody who was permanently on the road, like a traveling press secretary.

What were you learning? Or now that you’ve learned, tell us, how does a speechwriter take on the voice of the principal?

It’s a process. I remember asking Cody Keenan, who became his head speechwriter in the White House, “How do you know when you have somebody’s voice?” He said, “You’ll know it when you know it,” which was not helpful to me at all. [laughter] I was looking for “three months, four months,” and that’s not what he gave me at all. You just have to immerse yourself in what somebody has written and said. I read both his books. Cody said he listened to the President’s books as he drove to Chicago from Boston, I think.

Did the President read his books? You said he listened.

I think it was an audiobook.

As recorded by the President?

Sometimes those are recorded by the author. More commonly, they’re recorded by a third party.

Right. I know his most recent book he recorded himself. I think he did The Audacity of Hope as well.

That’d be interesting to find out.

I don’t know if he did Dreams from My Father, the first book. Cody said he just listened to them. You’d listen to every speech you could find on YouTube. You’d read everything that he wrote, and little by little you’d understand, here’s how he structures an argument. Here are some words he uses and doesn’t use.

A lot of this has become cliché with Obama. He repeats a lot of the same types of things. The first step is you start doing an imitation of somebody, and then, once you really get into it, you can start thinking a little bit more like them. That’s where you want to get because you’re not just trying to do an impression, you’re trying to actually channel what that person would think, and that takes a long time.

Now, let me ask you. Do you physically impersonate? [laughter]

No.

In my own experience, I can remember people physically impersonating. And I didn’t know whether that was commonplace in presidential speechwriting, where somebody would sort of take on the character of Barack Obama as they’re working on it.

I was never very good at an Obama impression. It might not surprise you here. Eventually, when I would write something, I’d kind of hear his voice reading it. And there’s also a musical quality to speechwriting sometimes. You need that cadence. I’ve gotten guidance from him where he’ll say, “I feel like we need to end on a few quick beats like this.” And then you’ll see that a paragraph is supposed to flow a certain way. It’s almost like a musical feel more than anything else. But then I remember it was hard to break out of. When I was deep in that, in his voice in the White House, I would find myself writing emails to friends as Barack Obama. [laughter] And I had to be like, Whoa. Then after I left, I had to rediscover my own voice again after living in somebody else’s head.

Can you give us an example of one of your emails in the Obama voice?

Oh, I’m sure I could. He’d do things like, “I reject the notion that this happened.” Or, “Look”—that’s one of the famous ones.

I was going to say, “Look.” It’s equivalent of Ronald Reagan’s “Well.”

Yes, and lots of, I don’t know what it’s called, but sentences and then you have a dash and he kind of continues a piece of that sentence on for a little bit longer. But, yes, it took a while to break out of that.

So it’s almost like learning a foreign language, isn’t it, where you hear something and you try to say it and repeat it with the right accent? And then they always say if you start to dream in what is to you a foreign language, you know you’re onto that. So I guess it’s very similar.

Yes. I never met him until we were in the White House, and it’s even weirder to be in somebody’s head and never have met them. [laughter] Or I guess if you’re Barack Obama, to know that there are people out there who are trying to get in your head and you’ve never met them.

Well, do we want to say, “Tell us about when you first met him,” or continue in chronology of the summer?

I’m curious about the campaign and things.

Yes, same here, and the [Democratic National] Convention. You start in June of ’08, so take us through up to the convention at the end of the summer and then the general election campaign.

This is probably just looking back, and maybe my impression is a little bit different looking back. It almost felt like the primary was tougher than the general election, at least for those of us in the campaign. I remember when Sarah Palin was announced as the vice presidential candidate, we were really worried. My parents were visiting at that point. They came into the office with me and met Anita Dunn, and she said, “Don’t worry. It’s a long way to go.” Because everybody was thinking this could be the end. He might’ve found the magic bullet to win this thing. But she was pretty circumspect about it.

And then I just remember that eventually the focus started to come down to fewer and fewer states. They would bring more and more people in the office who had been in other states that they felt good about, and then sent people out to some of these ones that they wanted to close. So the office got more and more crowded, and the energy went up and up and up. As the intern, I was just trying to soak it all in. And because of the nature of the Obama campaign, you’d look up one day and Jimmy Buffett would be walking by, and Spike Lee’s in the office. It felt like you’re the center of the universe. And, of course, I’m not in the meetings where they’re looking at the numbers and thinking about that stuff. We were just churning on and on and on.

Then as we got closer to Election Day, you got this sense that people were feeling pretty good about it. I wasn’t terribly involved in the convention. I did some research for the address and watched the speechwriters do it, but I wasn’t traveling to Denver for it. I just watched that with other interns and friends.

But I do remember helping Favreau with some research for the election night speech. I think somebody else wrote a speech if we lost, and I actually did that in 2012. I was the one who wrote the speech if he lost to Mitt Romney, which was a terrible exercise. I think the fact they had me write it lets you know they weren’t actually that worried about it. You feel like you’re about to jinx something if you’re writing a victory speech.

But I remember the energy around that night was electric. I went down to Grant Park before to see the setup before anybody was there, and you realize the scale of this thing. Then it builds and builds and builds on that night. All the TV trucks are downstairs. People are in the office. I really felt like I had crashed a party because I had been there for six months. I was like, This is great. And some people had been there for years, since way before anybody thought he would win, and this was the culmination of an incredible gamble on their part.

I remember there was a documentary crew in the office that night that he won. And Jon Favreau, my boss—There’s a story at the end of the election night speech where he talks about this lady, Ann Nixon Cooper, who was 102 years old, and she voted for Obama. I think she was born before women could vote and before African Americans could vote, and now she had just cast her ballot for the first black President. And so Favreau was talking to her on the phone in the hours before that speech, and she said, “Is it going to be on TV? What channel is it going to be on?” And he’s like, “It’s going to be on all the channels.”

And then just walking down to Grant Park with the people that I’d spent the last six months with, and seeing it delivered live, and feeling like this thing had changed everything and nothing would be the same afterward. It’s the kind of experience that I know I will never be a part of again, which is too bad, but I’m incredibly lucky that I had that chance.

This is the height of being sublime. But on a more mundane basis, what would a day look like for you, say, during the heat of the campaign? You’re living with your relatives. What time do you get up? How do you get to work?

That’s a good question. I’m trying to remember back then. I walked about a mile to the campaign office from there. Of course, this is summer and early fall in Chicago, which is great. I was like, This city’s amazing. I think after I left in November it snowed every day for a month, but I thought it was great. I’ll say—and you might remember this after graduating from college—looking back, I had no idea how to be in an office. I had just been in class in college, and so I don’t think I was as proactive as I should’ve been. I was trying to find little ways to help and anticipate what some of these writers would need, but I didn’t really know everything that was going on. I was just trying to be worth taking up this seat in the hallway of this campaign. All the interns had to do shifts on the phones, so I would be answering calls from people that would come into the campaign. I’d do the research for the speeches. I would just kind of help out however I could. I wish I remembered more about it at this point.

What’s happening is the economy is collapsing, and we’re about to roll into another Great Depression if we’re not careful. Were you having to do any research on that, the economy and global finance?

Yes. What I remember—and you probably got this from other people—is that meeting that George W. Bush, President Bush, hosted with [John] McCain and Obama at the White House when everything went down.

Yes, and congressional leaders.

I remember watching the stock market tank with people in the office. I remember I was outside this glass office where the speechwriters were. At one point, Favreau was on a conference call with Obama and the other senior leaders where Obama recapped that meeting and was shocked that McCain didn’t really say much. I think that was the news that came out of it. And I think Secretary [Henry M.] Paulson was on his knees begging people to do something. I think that was a wake-up call to everybody: OK, we’re going to have to get down to work, and this is going to be really tough, and it’s probably going to have to start before this is even over.

I’m trying to remember—you probably know better than I do—if he gave any big economic speeches before being elected, but I’m sure I did some research on that. The funny thing about the research that I was doing—this is more true for the White House—when the other speechwriters would want to look at the speeches of other Presidents, they weren’t looking at every President. They were looking at maybe five or six that they thought were actually good speakers. It was Bush and Clinton, Reagan, [John F.] Kennedy, FDR [Franklin D. Roosevelt], [Harry] Truman sometimes, LBJ [Lyndon B. Johnson]. I got really familiar with the speeches of other Presidents because, at least in the beginning, they wanted to know how they were supposed to do this stuff.

What did you pull out and offer to them as nuggets?

Typically, for a speech—in this case, more into the White House time—it would be the speeches of the most recent Presidents and speeches that we thought were good from way back when about a certain topic, stuff that Obama had said before. Research about the location, policy stuff that we got from the policy team, basically any kind of background that they would need to write something new, by looking at everything that had been done before. That was also true for the inaugural addresses and things like that that.

Given your internship with Senator Kennedy, I did want to mention two things that I’m sure you were well aware of but just wondered if you watched them. One is Senator Kennedy and his niece Caroline Kennedy going to American University to say he was casting his lot with Obama. And Caroline Kennedy saying something that you’ve just shared with us, which was, in her case, saying very personally that for her whole life people had come up to her to say how much her father meant to them and how much he inspired them often to go into public service. She said, “I always wanted to find a presidential candidate like that, and I have found it in Barack Obama.”

And Ted Kennedy casting his support for him over Hillary, both colleagues in the Senate. I’m also thinking of Ted Kennedy’s speech at the convention, which was sort of his swan song because of his illness at that point. But did you see those and think to yourself, Gosh, I interned for him. He’s a crucial piece of Obama’s success.

I remember those moments being huge. Cody Keenan, my colleague, had written for Senator Kennedy for a long time. We actually had met when I was a high school intern and he was answering the phones in the office. He didn’t remember me, but I remembered him. So it was much more personal for him. But I think, yes, looking back, you’re like, Of course he was getting these endorsements. But at the time—you know better than I do—it was pretty unusual for somebody like Senator Kennedy to jump in at that point.

Right. I think I was mentioning the other day that we had a call from former Senator Don Riegle from Michigan, who was really good friends with Senator Kennedy in the Senate. He’s done an interview for the Edward Kennedy [Oral History] Project that the Miller Center did, and he’s in the process of editing and getting ready to clear it. He wanted to get some information about that, but he went on to take a good chunk of time to talk to me about his friendship with Senator Kennedy.

He said, “You know what would be an interesting piece to write is how senators divided when it came to casting their support for Barack Obama or Hillary Clinton. I remember that time, and I so well remember my friend, Teddy, deciding he was going to go with Obama and encouraging Obama to run.” And saying, “The brass ring sometimes just comes around once, and moreover, the longer you’re in the Senate, the bigger record you have that people can take potshots at you on.” It’s fresh in my mind to be even thinking about that. And here you have this confluence of two people you’re working for who are so important in American history.

I felt really lucky to be on the very outside of both of them, especially Senator Kennedy.

OK, so you’ve been working for the President-elect of the United States. You wake up the morning after the election. What are you thinking about?

The weird thing about presidential campaigns is, it’s just done and everybody starts to pack up and go home. Then it becomes this weird scramble for jobs in the White House, and there aren’t that many. What I always felt guilty about was that I said to the speechwriting team, “Hey, I’d love to work with you in the White House,” and they said, “Yes, great, we’ll do what we can.” But a lot of people who’d been busting their tails for the campaign for years—in the field, especially—there wasn’t a direct job for them in the White House. I always felt kind of guilty that there was one that I could go into but not that they could necessarily go into.

How did you find out you were?

Well, I didn’t for a while. This is in November. I went home, lived with my parents again.

Start paying them back yet?

No money coming in yet, [laughter] so I still had that debt. I had checked in with the speechwriters once in a while, and obviously the personnel stuff is just crazy after somebody gets elected. They kept saying, “Yes, we’ll do what we can.” My dad was really nervous at the time because I was up for a research assistant job, which was the lowest on the totem pole. He thought that it would go to a child of a donor or somebody. Anybody could do it. But I probably naively thought that I could have a shot at it. And I think what benefited me was the fact that I was the intern they had seen for the last six months.

At that point, I had turned down the consulting job and then got a call to go into the transition office. They said they barely had enough money to hire me as a research assistant. I was on top of the world because we were all just excited to get going.

So you’re hired by the transition?

I think Favreau told me, “You’ve got a job when we start.” This would be on January 21st or something like that. He pulled me in to do research, and the whole time I had been doing some research for him on the side for the inaugural address. That wasn’t with the promise of a job. That was just like, “Hey, do you want to help out with this?”

And so you’re staying in their good graces, and you’re doing some interesting work. What kind of research task are you assigned with respect to the inaugural address?

It was a tough one because we’d never written anything like it before. It was a lot of pulling stuff from past Presidents. It was a lot of looking for some kind of hook, some historical event we could talk about. I think he ended up quoting a letter from Patrick Henry or something. I did a bunch of historical deep dives. The theme they were trying to hit was this idea that things were really dark at the time, but if we do the right things, America can get through it. I haven’t read the inaugural in a while.

I guess I’m trying to get a sense about your assignment. You’re talking with Favreau. Is he just free-associating ideas with you? Or is he saying, “Things are really bad right now. Go find me an example of a President who dealt with a bad problem.”

After becoming a speechwriter, I had more sympathy for this. When I was a research assistant, I would think, All right, what do you want me to go find? Just tell me. I’ll go find it. And he didn’t really know. As a speechwriter later on, I realized that you don’t always know. Sometimes you’re just looking for something that sparks an idea that gives you a hook for the beginning or the end, or an idea for a riff. I think he was looking for anything that would compare to the moment that we were in, anything that would speak to the themes that he and the President were trying to hit. I did binders and binders of stuff. I would say of all the research I’ve produced, for some of these bigger speeches especially, maybe 10 percent of it got used.

A lot of it is stuff that the speechwriters just went through either for background knowledge or to know what they didn’t want to say. I was trying to desperately find that one thing that would be the conclusion of the speech, or the opening, or something like that, and I don’t think I was the one who found it. But he was just looking for anything that would—I wish I remembered. I’ll have to go look back through email about what the assignment was. But I think it was kind of like find quotes, find scripture verses, find anything that speaks to this idea of hope through darkness or something like that, the big thing they were trying to hit.

OK. It sounds to me like he’s relying a lot on your sense of judgment and understanding about the moment as you have developed a common rapport on your candidate and on what you hope to do with the presidency. So that rather than giving you a specific assignment, which is, I want you to go read every inaugural address from Presidents and help me figure out what thematics best match here, it’s more like, Go out and find me kindling. You need to help me find the sparks that are going to make this go.

I think it was more like that. He wanted to read the past inaugurals just because that gives you a sense of what these sound like. I think he’d also gotten some guidance from Obama about the themes for this one, and then his job was to turn that into a speech. And to turn it into a speech, you need a lot more than just the broad strokes. You need the stuff that goes into it. I think you’re right that he was—Looking back, it must’ve been an incredibly stressful experience, because all of a sudden you’re supposed to write for history. And up until then, as a speechwriter, you’re just writing for voters and a little bit for history when you do some of the bigger ones. But this is one that goes in the lists of ones that have been given. There are not that many.

I think he was feeling the weight of it and just looking for any kind of lifeline, including from people like me, to figure out, I could see where this fits in, or I see how this is going to come together to make the argument I want to make that’s not just our words but that’s other stuff that we can draw from.

To further this discussion, you get the sense that although this President has extraordinary eloquence as a writer and as a speaker, at least in my own sense of this and having conversations with a lot of people, he didn’t have much patience with florid language and overreaching the moment. So I would think it would be an even more difficult proposition to write for a person like that, for a speech where the conventions are, yes, you do reach for the florid and you do reach for this extraordinary eloquence.

Yes, and I think, to be honest, that’s why his inaugural address is not his most memorable speech, both his inaugural addresses. I think he’s best when he’s speaking in pretty normal language. And it’s a little bit elevated just because it’s Barack Obama. But if you look at something like the race speech, the most memorable lines, first of all, they’re not really sound bites. They’re just parts of the story. They’re not soaring rhetoric. He’s not JFK [John F. Kennedy] in that way. It’s more just like putting something into words that people can’t always describe and doing it in a way that hangs together in a big story. If I had to guess, and I wasn’t part of drafting the speech, but I think they might’ve tried to go a little bit too far from where his wheelhouse was.

I teach a speechwriting class at Batten [Frank Batten School of Leadership and Public Policy at the University of Virginia]. It’s a short course. I’m doing it right now. But one thing I tell my students is, don’t write something like you think it’s supposed to sound. So if you’re writing a press release, don’t try and do a press release like everybody else does a press release. Be true to yourself, and the rest will kind of fall in place.

It’s tough for a lot of Presidents in those inaugural addresses because you’re trying to sound like the famous ones, but that gets you away from yourself. It would almost be better if you just stood up there and gave the best version of your own thing instead of trying for something else.

We had a symposium years ago—and I don’t think this had been published by the time you were writing, I can’t recall—where we had White House speechwriters in, a dozen reaching all the way back to Ray Price, who had been Richard Nixon’s speechwriter. We did a series of sessions, and this is available on our website. We have a book out of it now. As I said, it probably wasn’t published. It wouldn’t have done you any good because you didn’t know it. But it’s interesting listening to people in your profession talk about the difficulties of writing an inaugural address. One of them said, “You’re writing for the marble, and you should never write for the marble.”

Yes, exactly.

But I think back to the predecessor, George W. Bush. And Michael Gerson—who recently departed, God rest his soul—could write florid rhetoric for George W. Bush, and for some reason it seemed to work. And Bush is a blank-kicking Texan, for Pete’s sake.

I’m surprised it worked because that’s not what I would have expected at all.

But with Obama, it didn’t work either, because his eloquence is a different kind of eloquence.

I think so, yes. He could elevate it a little bit. If you hear him speak at memorial services, if you hear him in front of black audiences, a lot of times he gets into the preacher mode, but it’s always his version of it. I’ve never loved the speeches of his that are almost too focused on the history, on being for history. In my opinion, his best stuff is when it’s meeting a specific moment.

We’ve done some of these in the past. We did speechwriters. We did the congressional liaison head, domestic policy advisors. I remember, again, listening to all of these people talk about this common problem.

The other piece of it was the impossibility of preparing a President for, physically, what it’s like to deliver a State of the Union message. They’re removed from the audience.

You mean inaugural or State of the Union?

I’m sorry, inaugural.

Well, probably both, which we’ll get to.

But more the inaugural address. The first thing is that nobody you’re speaking to is anywhere close to you.

You’re just looking at a big camera rig, yes.

Exactly. Then secondly, there is no applause because everybody’s outside in January, wearing mittens or gloves.

And by the time the sound gets down the [National] Mall, you’ve moved on. It’s weird.

Exactly. Particularly, yes, the people who are at the Washington Monument listening. Were you mindful of this at the time?

I remember some real nerves in the speechwriting team when they were putting that together because I think they knew how few of these actually get remembered. They knew how different it was from everything they’d done up until then, and they knew how big a deal it was. Sometimes that much pressure does not make for a great product. And I don’t mean to put down the inaugural address. It’s just not the one that people remember. It’s not the speech that people remember from him.

When you were given the assignment to go back and look at the others and particularly to find Presidents who were inaugurated and gave their inaugural addresses at darkest moments of the country’s history—presumably one would go straight to ’33 and Franklin Roosevelt coming in in the depths of the Great Depression—and maybe to say what you might not want to say, in one way. That is Reagan with the downturn in the economy, which helped him get elected and defeat incumbent Jimmy Carter, and not say the famous line, “In the current situation, government isn’t the solution to the problem. Government is the problem.” But Reagan was viewed as sunny and hopeful in times of darkness, and certainly we know FDR was.

Did you immediately think of that and start with at least the FDR one? But, as Russell said, also gathering the kindling you were assigned to get quotes, get scripture, get historical events that he can talk about. How did you even start to do that?

I remember going back and looking. The FDR assignment, I remember that one. That was one that they definitely wanted to look at. I think they were also interested in looking at JFK’s because he was speaking to a new generation, and that was something similar to what Obama was trying to do. I remember it was an incredibly wide net they were trying to cast because you don’t know what’s really going to hit. Yes, the assignment was, what have been the darkest times in American history, when the Revolutionary War might’ve been about to go off track or during World War II.

Existential moments for the republic, right?

Yes. And [Abraham] Lincoln, we looked at a bunch of his stuff, trying to figure out how the leaders at that time acknowledged what was going on, not trying to sweep it under the rug but at the same time inspire people to not give up hope, to believe that there’s a brighter day ahead. Some were more successful than others, but there definitely have been times where that’s happened and that’s worked, and I think they were trying to recreate a little bit of that.

When in the process leading up to the inauguration do you find out that you have a position?

I think that was early January.

OK, so about three weeks, maybe?

Yes, something like that.

Two to three weeks before the inauguration you find out you have a paid position as a researcher.

Yes. I was going to be paid $35,000 a year, I think, which was great. I was going to pay back my parents. I was going to hopefully be able to live somewhere other than my house. I started on the first day of the administration, which I think also happened to be my birthday, January 21st, my 23rd birthday. I went to the inauguration just as a regular person. I was on the Metro for three hours and got a ticket way far away.

Whereabouts on the Mall were you standing?

You know there’s that sort of pool? I think I was behind that a few rows, not a nice seat. They got me a ticket, and I was like, Great, I’m going to be there. I had a standing-room ticket way back with everybody else, but it was kind of cool to be back there and to see how excited people were.

And presumably pretty much mashed together. Having watched it on TV, it looked like people were just shoulder to shoulder, which might’ve been good because it was bitterly cold.

But not as big as the [Donald J.] Trump. [laughter]

No, not even close. Yes, that was cool. And then knowing that next week or the next day—I probably started a couple of days later—knowing that I would get to show up and try to figure this out.

Describe that.

It was weird showing up. It’s almost like people in a fantasy camp. You have all these people who have watched the West Wing, who know what this is supposed to look like. And unlike any job—I’m sure you’ve heard this from other people—you show up, and there’s nobody there. There are computers for you, and there are some staff that go from administration to administration. I know the speechwriters had gotten to meet with George W. Bush’s team. Marc Thiessen, I think, was the head speechwriter then, or somebody had walked them through how the office works. But the first day, you’re just walking around. The people who are in the West Wing are like, “Hey, come on, I’ll show you around here.” They give little impromptu tours.

Had you reported to the Old Executive Office Building?

That’s where my office was, and most of the speechwriters were there. Jon Favreau and Ben Rhodes were in the West Wing in these underground offices where no sunlight ever got to. It’s this weird situation where you’re excited to be there, but you also know, Now I have to get to work and do all this stuff that we talked about doing, and not really knowing how to do that, having to learn on the fly. It still amazes me that these transitions work as well as they sometimes do because there’s really not much help there. You’re just in there doing it, trying to figure out how to do it.

What’s the shop setup like, and how is it organized? How is it run day to day?

You talk to the previous administration. You figure out how they did it, and then a lot of times you try and do it a similar way until you realize that you want something a little bit different. Every morning the speechwriters would get together in Favreau’s West Wing office and go through the speeches for the next week or two and assign them out. You’d usually get one or two speeches a week. I think in the early days they were trying to do way too much. He was speaking too often.

When you say “you,” do you mean the office, the plural you, or you individually, people would be assigned one to two speeches per week?

Individually, yes. Favreau would be in the senior staff meetings where they would say, “OK, here are the events we’re doing this week where we need to have speeches.” He would bring that to us and say, “OK, we have these five or six things we need to get done. Who wants to do this? Who wants to do that?”

I think at the beginning, they assigned speeches based on issue area. So maybe somebody would do all the health care stuff, and somebody would mostly do the economy stuff. I think we realized pretty quickly that that didn’t necessarily work. There are too many different things, and you’d have to just do a little bit of everything. People would still have specialties. Cody Keenan always liked doing the labor. Jon Lovett, who was one of our speechwriters, liked doing the science stuff. And so you’d have specialties, but usually it would be trying to get this balance of who’s got time to do something, who wants to do something, and people would divide it up.

As the research assistant at the beginning, my job would be to go to each of those people and say, “OK, here’s what I’m planning to pull for you. Is there anything else you’d want? What angle are you thinking of taking on this? What else do you need?” Then I’d go prepare binders for the writers, and then they’d come back to me with more stuff to go get. It was like doing a research for a term paper multiple times a week every week.

And were you the only research assistant?

Yes, at the time I was.

That’s a lot of work.

Yes, it was a lot of work. You’d get to know the different styles of the different writers, and what they liked and didn’t like, and what they needed. I was always amazed at somebody like Jon Favreau, who didn’t outline his stuff. He would just read everything and then start from the beginning and just write all the way down. I’ve never been able to do that. I’ve always been an outliner and somebody who needs to see the whole argument before I actually start filling it out. But he was really, really good.

And just like on the campaign, they started giving me little stuff to write. If a sports team would come to the White House, I would write that. If we had some weekly address—he used to give these weekly video addresses—I started doing those. Then, little by little, I started getting to write bigger and bigger things. It’s the best training as a speechwriter because we had people later on in the administration who would come in from one of the Cabinet agencies or somewhere else and just be plopped in to write for Barack Obama. Some of them had a tough time because it was a completely new voice and a new person, and they’re writing a 20-minute speech for this new person. I was lucky in that I got to do little stuff and then bigger and bigger and bigger stuff. It didn’t feel as jarring when I was all of a sudden writing a full speech because I’d been doing smaller speeches, and they’d been getting bigger for a long time.

How much discipline is exerted? I mean, is this a collegial, friendly process, or are your superiors gruff and rough on you? Are you learning by coaxing, or are you learning because they’re using the rod more to say, “This is a piece of shit here. I don’t want to see this kind of stuff anymore.”

Are you talking about the research or speechwriting?

A little bit of both. Most of the interviews we have done are with the speechwriting directors, the people who are heads of the shop. And so we get a very different picture from them because of their relationships with their colleagues elsewhere and also with the President. What we don’t hear very much about is the mechanics, what it’s like in the boiler room, which you can help us understand.

I heard that in the Bush administration, a lot of the speechwriters were gathered together around a computer and would write something together, which I’m really impressed with because I can’t imagine how that works. [laughter] We did not do that. Writers, I think, are just by nature kind of anxious and neurotic, and they have this imposter syndrome. And so a lot of it would be me trying to help people out in the way that they needed to be helped out. One guy would wait until the last minute and then write all night, and so I would help him work through that in the beginning. Other people knew exactly what they wanted. I wouldn’t say anybody was rough on me. I think they were nice enough.

But I learned later that there’s nothing more stressful than knowing that you need to turn in a draft by this afternoon and having a blank page in front of you. So I would not blame people if they were in a bad mood with me because I knew it wasn’t about me. It was about what they had to do. My goal would always be to get somebody something before they needed to ask me specifically for it.

When I give advice to college students, it’s like, if you have a boss, try and anticipate that boss’s needs and also make them look better in the eyes of their boss, and it’ll work out. My job was, to whatever extent I could, to anticipate what they would need, what would make their job easier. Then if they didn’t use anything I gave them or if they were not happy about something, to try not to take it too personally because everybody’s feeling the pressure in that kind of environment, and people have their different styles.

I saw in the background materials that the speechwriting shop would meet with David Axelrod. That was daily?

I think that was daily, yes. I would come to many of those, not every one. That was the most fun time of the day.

He’s a character. First of all, in his office he would have five ties on the back of the door because he would spill on his ties constantly and always need to be changing them. [laughter] He was our main guy. When we couldn’t talk to the President, Axelrod was the guy who knew him best. He would be the one to give us guidance on what we needed to write about, the angle he’d want to take. But mostly those times were just BS-ing with him. He was a huge pun guy, so there would be runs of 10 minutes where you’re just making a ton of puns about things. I think he really enjoyed it because it was one of the lighter moments of his day.

He would always say, “Hello, wordsmiths,” when we’d start those meetings. It was very light. You’d try and get some kind of guidance out of it, but it was mostly just him having fun and us trying to pick his brain on the million different things the President had to do every week. I was intimidated because I’m not that good at puns and I was trying to just keep up. But he clearly enjoyed it.

When he retired, we made this book of all our favorite speeches that we had worked on with him. We all wrote notes for him in the beginning, and he was touched. We had other people who’d give us guidance from a higher communications level in the White House, but he was always the most fun.

So that leads to messaging. Tell us about coordination—I presume there’s coordination—with the communications director, who was [Daniel] Dan Pfeiffer, if not always from “Axe,” as they call him. Are you getting not only, “Here are the speeches, here’s where the President’s going to be speaking this week or next week, and here are the speeches we need,” but also getting, “Here’s the messaging we’re trying to get out about what’s happening,” especially in those first few months when the economy continues to tank?

We always seemed to have one person who was our messaging guru. It was Axelrod in the beginning. David Plouffe filled that role a little bit later, although he wasn’t as much messaging as logistics and the political side of things. And then Dan Pfeiffer filled that role later on. We just always needed somebody who knew the 50,000-foot version of, OK, what are we trying to do here? What message should we be pushing? We got the details on what the event was from other people, but then the communications director would always be the one to say, “OK, here are the main points you want to hit,” just giving us one level deeper of messaging guidance.

Then we could go and fill it in with policy stuff and everything else. Because if you go to the policy people, they’re going to tell you, “You should put in these 15 different things,” and they’re really complicated and nobody understands them. So we needed somebody to say, “OK, here’s the main story you’re trying to tell.” And maybe, “Here’s what we’re trying to do from a strategic perspective,” and then you go and at least have that with you.

What’s the President’s role? Did you see it or did you hear about it? Because once all these speeches are churned out, or even the Saturday radio addresses or the team is coming in to talk sports, what do you gather as the President’s role? Does the individual who’s written the speech go meet with him and he says, “Yes, I’ve looked at it, and here are all the changes, so please do this,” or, “It didn’t quite hit the mark, please do this to it”?

Typically, what we would do is, if we had a bigger—We would all go meet with him maybe once a week.

As a group?

Yes. We’d have our daily speechwriting meeting. We’d have our daily communications guru meeting. And then we’d have the President once a week or once every couple of weeks. Everybody who had a bigger speech to do would go to that meeting. You’d go around and ask him—basically, present your idea for it and ask him what he thought.

Sometimes he was more engaged than others, and sometimes he would say, “Actually, here’s what I want to say.” And he would outline something for you, which was a jackpot because you would just type as fast as you possibly could, and then that would be the bones of the speech. Sometimes he would say, “I don’t know. I don’t really know what I want to say here.” Then you’d have permission to go do whatever you thought would be best.

Then you’d write that speech. You’d get help from the other speechwriters. Then you’d send it to a group of about 20 or 25 people who were the core group of people you really needed to listen to. These would be the David Axelrods, the policy experts, the people whose edits you really needed to take.

Then the night before the speech, it would go to “the book.” That’s all the stuff that goes to him at night. You’d send it to the book list, which would be another 20, 25 people. These are people who should see it before it goes to the President but who weren’t a big part of drafting the speech. You’d make your call on whether to take their edits.

And then the next morning, usually the morning of the speech if it was a smaller one—bigger ones you’d do a few days in advance—you would get a physical copy of that speech back, usually with his handwritten edits on it. Sometimes they’d be minimal. Sometimes he would write in the margins all over the place and move things around. That was actually good because he was engaged with it, and you knew that he had paid attention to it. The worst was when you’d get a note at the top that just said, “Please see me.” [laughter] Then you knew he was going to go in a completely different direction, and you were going to be working like crazy to get this thing done in time. That was never good.

Usually if it was a daily event, he’d stand up and give the speech. Or if you were traveling, you’d travel with him. He’d usually have some more edits on the plane, and you’d put those in right before you got to the venue. The ones that made me a little nervous were always the ones where there weren’t that many edits because I wondered, Did he actually just not really read this? How’s this going to go? It was always tough to get a lot of edits, but that always made for a better speech because you knew that he had been engaging with it.

[BREAK]

Are you getting stuff out of this? I’m not asking for validation, but I just hope it’s useful.

It’s exceedingly useful.

You may not be asking for it, but we’re going to give it to you. Because as Russell said, first of all, I’ve been at this 12 years, and he’s been at it over 20 years. But we’ve never had someone with the kinds of experience you had: starting as a researcher, working your way up through, and doing the campaign. Plus, your life story, your personal story, is great because imagine students, particularly, reading this years from now. You’ve given them a roadmap of how to follow their dreams, particularly to be a speechwriter. But just generally, like where you said, “I didn’t know really what went on in offices. I wish I’d been a little bit more proactive.” That kind of general advice for an undergraduate or a high school student is fantastic.

There’s also a lot of luck that goes into it. I mean, like we talked about, if I had graduated UVA a year earlier, it might not have happened.

Yes, right. It’s been assigned to Bill Clinton, Lee Trevino, “The harder you work, the luckier you get.”

[BREAK]

Where were we?

We were talking about the role of the President in the speechwriting process. Anything else to add on that?

No. I mean, the funny thing is I’m President Obama’s speechwriter now. I’m his chief speechwriter, and so it’s weird to be able to work with him much more closely now than we did in the White House. He has a lot more time on his hands. But he’s the same guy. It’s the same kind of thing.

Well, to keep our chronology, we’ll circle back to that in the postpresidency because that is fascinating, to be sure.

Tell us, as you move up from researcher to being given smaller speeches to work on, at what point do you move into working on full speeches? I started to jot down the various speeches that you may have contributed to. You can say, “Didn’t have anything to do with that one,” or “Did that one and did research on it,” or, “Actually wrote the first draft of that.” One of the first ones I’m coming to is the President’s first speech to Congress, when he’s just come into office, so you’re in the research realm, but it’s on terrorism and health care. Anything to report from that? And then I’ve also got into April of ’09, then the Georgetown speech that uses the theme of the Sermon on the Mount.

I have to apologize, I think for a lot of these that I was a researcher for, I contributed some stuff but I don’t really remember exactly what it was, just because we were doing a lot of these really quickly.

Well, I did have a question on religious themes. One of them is—and I think you’re correct, as I always saw it this way—Obama as preacher and sort of call and response. And that also relates to another point that I wanted to raise. He gets the speech. You described in great detail, very helpfully, the way he would participate or not in that process. And yet, I always thought, watching him, and even recently watching him give speeches—Before the midterms, for example, I watched the one he did over a weekend in Detroit. That is just so superb in terms of what seems like ad libs or going off script in a good way. And then that rapport that he gets with an audience that feels like call and response. “Fired up! Ready to go” is literally a call and response. And then the Charleston speech after the shooting, where it’s a literal singing response.

To what extent, when you do begin writing speeches, are you aware that at any point he might go off script? And do you just accept that? That’s always noted as one of his strengths, and that is done really well.

But when there’s a religious theme that you’re either asked to research or you’re writing speeches at some point and you’re putting in religious themes, one question I had particularly was about Josh DuBois. He is the in-house supplier to the President of these daily religious meditations and scriptures and a meditation on a scriptural passage that he’s supplying every day. Is the speechwriting shop ever working with him on that?

Yes, for sure. Any time we had either a speech that was religious in nature, like a prayer breakfast, or if we were doing a eulogy where it would help to have some scripture in there, Josh would be our first call. The funny thing was, like a lot of people in the Obama White House, he was really young and came from a family of preachers, and so he had some deep knowledge of this stuff. The people that were the most valuable to us in the speechwriting office were people who were experts but also had an ear for what would work in a speech.

This is especially true for economic policy. So somebody like Brian Deese really knew, OK, I’m not going to give you a million different things. I’m just going to give you the points, and I’m going to explain this in a way that you can explain it to other people. That was always really helpful.

Josh, I remember, was very good. We’d say, “OK, here’s the theme we’re trying to hit. Here’s what we’re trying to get across. Can you get us a good passage? Is there something you’ve given the President recently that you think might work here?” And he was always good with doing it in a way that he knew would fit with what we were trying to say.

Given that there is this thread of religiosity and faith for the President, but also knowing the controversy that related to that in the campaign via Reverend Jeremiah Wright, did the speech shop have to take that into consideration? About how he was presenting himself in faith communities or things he was using in speeches related to religion and faith?

I worked on some prayer breakfast remarks, which were his main explicitly religious way to talk. I’ll say, those of us on the speechwriting team were not particularly religious, so it was a little bit of a stretch for us to inhabit somebody who was more religious.

His faith seemed to be more of a private thing. He wasn’t somebody who would just talk about scripture in normal conversation. But I think it informed a lot of the way he saw the world and the way he thought about different policy decisions, especially some of the lessons about treating your neighbor as yourself and some of the basic stuff that underpins a lot of different religions.

So whenever we would do something like a prayer breakfast, we would try and find a lesson that we could apply to something happening today—not just a meditation on scripture but, like a lot of great preachers do, taking inspiration from something that was in the Bible or somewhere else and applying it to whatever was going on in the moment.

It’ll sound random, but I do have a question—part of the way we were able to link to you was through your friend Kyle Matous. Bill Antholis, our director, at one point had said, “Oh, you should really get to know both of the Kyles who were here at UVA. They land on different parts of the spectrum politically and ideologically.” Tell us a little bit about that. We don’t need to get into the details of your friendship, but you clearly are open-minded about people you engage with. You’re not so into an ideology that people say, “Oh, I can’t possibly have this person as a friend. That person is conservative, or that person’s liberal, or that person’s a Democrat.” Where does that open-mindedness come from?

A lot of that came from being friends first, I think. I felt lucky in that a lot of people that worked in the Obama White House, their best friends also worked in the administration. They lived together, and they worked together, and they spent time on weekends, and they sort of existed together.

I went to UVA, and a lot of my friends from UVA moved up to D.C., so my closest friends during that time were from college. I would hang out with people like Kyle and other friends of ours. He happened to be working in Republican politics. We were friends first. I always thought it was really useful to have at least one friend [laughter] on the other side of the aisle because so much of what was going—He was a staffer for ]Peter A.] Pete Sessions at the time and Richard Shelby from Alabama. Actually, it might’ve been his wife. But anyway, they were involved in that world.

But it was always nice when we were working on something—especially if it was going against a Republican policy, or if they were going against us—to be able to call Kyle and say, “OK, what are you thinking about over there? How do you see this?” I knew that we would still be friends at the end of it, and he could give me a sense of the other side. I think for a lot of people in Washington, if you just stick to the people who see the world the way you do, the other people are a mystery. You’re talking about what Republicans think, but you don’t actually talk to a lot of Republicans.

It’s always good to have somebody and to realize that they might have a different perspective on something, but they’re not crazy—at least most of them—and there’s a reason behind it, or it follows some ideology. I always thought it was really useful to get his perspective on stuff.

Very helpful. How about comedy? I’m thinking comedy in several ways. One is “public speaking 101,” open with a joke. There’s that. So for every speech, did you always think in terms of, there has to be some levity to begin with or somewhere in the speech? And what about those speeches, like for the White House Correspondents’ Dinner, that have to be all comedy?

The little jokes at the beginning of speeches, in speechwriting that’s sometimes called a “handshake.” It’s getting the audience to be on your side before you start. We would always try for stuff like that, even if was a sports reference—depending on where you were—or some joke about why he was there, something that would make the audience at least feel a little more relaxed before you he got into the main speech. I always liked doing that. It didn’t have to be that funny.

I think for a President, you can’t be really funny. There’s almost a limit on how funny you can be because it could be inappropriate. I feel like President Obama has always had a “dad joke plus” sense of humor. You don’t want it to be a groaner, but you obviously don’t want it to be too edgy. Weirdly enough, I feel like that’s where I fall too. [laughter] It’s worked out pretty well.

You were talking about the midterm speeches. That’s where we got to do a lot of that. I wrote those speeches with him. That was a chance to say, OK, how funny can we be up to a limit when it might be—?

These most recent midterms?

Yes. So, what can we say about Herschel Walker that’s not going to be nasty but will be a little funny? That’s always been the challenge. At the beginning of speeches, that was something I could do. I never was one of the main writers on those comedy speeches because that was a new level.

We always seemed to have one writer on the team who could write comedy. It was Jon Lovett for a long time, and then David Litt, and they would take the lead on it. They would come up with a list of topics like, OK, here are the topics we could potentially joke about. And then they would put that list out to all of us and some professional comedy writers, including people like Judd Apatow, who did a bunch of movies, and get ideas back. Their job would be to cull through all of them for the best stuff and then make it flow somehow so its not just one random joke after another.

If you ever just sit there and try to come up with a joke about the debt ceiling, it’s impossible. [laughter] You might think of something funny when you’re talking to somebody, but just sitting there in front of a computer, you think, All right, what’s the funniest thing I can say about this? I always found it was so difficult. Of the ones I would send in, maybe one would make it in, but a lot of them would end up on the cutting room floor. I would get really stressed out, and then nothing would get picked. The President really took those seriously. I think he thought of himself as a funny guy, and his delivery is good. When we would go in to present that speech, he would always say, “OK, so are you guys going to make me funny this year?” [laughter] And we’re like, “Yes, some of this is on us. Some of this is on you.”

The two that I always think of that are really shticks, one is the Bill Clinton film. At the end, his last one that they do a whole film that they show. And it’s a joke on himself about Hillary running—

I love that one.

And that’s Jeff Shesol, I think, who wrote that script. I love it where she goes off in the limousine outside the South Portico.

“You forgot your lunch.”

“You forgot your lunch,” and he’s got the brown bag and he’s watching the laundry go around, washing the limousines. I always think that’s a brilliant one. But also Laura Bush’s, where she sent up her husband about how he went to bed so early, and her delivery was really good. So in those comedy speeches for that particular occasion, that everybody knows is when the President has to be a stand-up comedian, is there a theme where they say, “Let’s do a film,” or “Let’s do Laura sending up W. for being boring and going to bed so early,” or is it, “Let’s just see where these topics take us”? And most of the time it’ll be a series of topics and funny comments about issues.

I’m trying to remember if we did any set piece videos like that, and I don’t remember one. There might’ve been one. But a lot of times those took a lot of the President’s time that he didn’t necessarily have. I heard that when they shot that video, they had every scene set up at the same time, and the President just went from one to the other and shot every one in the course of half an hour or something, so that takes a ton of coordination. I think we thought about something more general like, This is going to be the focus of this. But also, if that doesn’t work, then you’re stuck on it for a while. So where they landed eventually was, they would have—the best thing I can think of is, do you remember Obama’s “anger translator,” the Keegan-Michael Key—

[laughs] Yes, that was really good.

They had him as a guest for one of his last ones. That was great because they were in person. They were playing off each other. But a lot of times besides that, they would just do individual jokes. You kept it moving. If this doesn’t work, maybe something else will.

Right, like a stand-up comedian or a late-night comedy monologue.

Right. Also, being able to trust him as a good deliverer of jokes. I could see Presidents who might not have been that good at delivering jokes and needing more of the preproduced “Let’s make it so he can’t fail that much” kind of thing. So, yes, we were lucky there.

So 2011 is the now-famous poking, a bit of a stick in the eye, of Donald Trump in the audience. Any thoughts about that at the time that you were hearing about it, or when it happened, or now in retrospect?

I remember when that speech was coming together, and I don’t remember thinking that it was an enormous risk, possibly because at that time nobody really thought Donald Trump would be a serious candidate for President. I think after the birth certificate stuff, the birther thing, the President was annoyed at Trump, and I think it made that a little sharper than it would’ve been otherwise. That’s a little bit of Obama’s sense of humor sometimes. He’s a competitive guy, and if he sees somebody who’s come after him and now he has a chance to come after them, he’s going to do that a little bit. So I think it probably made him feel good in the moment.

Looking back, it seems maybe not the best idea, but at the time, it was, This guy’s been kind of a jerk for a while to us. Let’s see if we can send him up a little bit. And they did. I don’t think that’s why Donald Trump ended up running for President. I remember thinking that it was funny, maybe a little edgy, because there was that little bit of a personal background thing. But not, Let’s see how this goes, could be a disaster.

I wonder if you could talk a little bit about the process for the State of the Union message, because that comes up on a repetitive cycle. I’ll leave it open-ended like that. Tell us what went into it. How early do you start thinking about it? How is the preparation for that, because of where it sits on the calendar, different than these other speeches?

We started preparations on that much further ahead than almost any other speech. So if it was, say, mid-January—I don’t know when it was traditionally happening—we would start in early December and have at least a couple of months on that. And I was never the lead writer on a State of the Union. But talking to people who were, there’s a line that the State of the Union is the speech that every speechwriter wants to write until you’ve done it, [laughter] and then you never want to do it again.

What ends up happening is—you’ve probably heard this from other speechwriters—every policy person wants their bit in the State of the Union. And if it’s not in there, they feel like, Well, nobody’s going to care about it. The President doesn’t seem to care about it. The result is, you’ve got stacks and stacks and stacks of paper of all this policy that people want in there. And you need to figure out how to not only get it in there and talk about it without going on for three hours, but have it fit together into some kind of story so it’s not just talk about immigration, talk about health care, talk about foreign policy. That was always the biggest challenge for speechwriters. What’s the story we’re telling, and how can we avoid those really hard transitions that don’t always make a lot of sense?

Now, I think in one of [Joseph R.] Joe Biden’s [Jr.], the last couple of State of the Unions, he just did that. He said, “OK, now we’re going to talk about immigration,” which, to his credit, was a good idea. Don’t even pretend to tie them all together. But we would try. My job a lot of times would be to take a section of that speech, so Cody, or whoever our chief speechwriter was, would say, “All right, can you take this education stuff and write four paragraphs on education?” And then we’d try and fit it into the bigger speech. He oftentimes delegated foreign policy stuff to Ben Rhodes or Terry Szuplat, our foreign policy speechwriters. And then the person who’s in charge of it just tries to pull everything together. The worst part is the editing process where you send it out to people and everybody’s suggesting everything.

It’s just a frustrating thing. Every year Obama would say, “Let’s do something different. Let’s do a short speech. Let’s do a written message. Let’s go out somewhere else in the country and do this.” And it never happened. We always ended up doing the traditional thing just because it’s a lot of inertia. It’s a lot of history, a lot of expectation. You are getting the biggest audience that you get all year, people watching this. Yes, it’s difficult to do something different, even though something different is probably required.

Were there specific advocates for “No, we have to stick with the existing framework”? Or is it just inertia, and ultimately the amount of energy that would be required to break the mold was judged to be too much?

I think it was probably the latter. I don’t know if there was ever a real attempt to keep it very short. But I could see if that happened and you cut whatever issue, the person who was really passionate about that issue would raise a big stink with a domestic policy advisor or somebody else. Then you say, “Well, let’s add a little bit of that,” and then you end up back where you started.

When you’re doing research on something like the State of the Union, is there an expectation that you’re going to be fishing in whatever waters you can find on the subject? I guess I’m trying to get a sense about your relationship with the departments, with the rest of the executive branch. Because we understand, again from this huge corpus of interviews, that there’s always a sense of independence within these departments while at the same time they’re knitted into a larger framework. I’m trying to get a sense from you about how you deal with that sense of independence when you’re doing your research and writing these big speeches.

I wasn’t the person to go directly to the Cabinet secretaries or the departments and ask. But I think what happened more often than not was that they would say, “What are your couple of priorities for this year? What do you want in this speech?” It really forced the departments to narrow things way, way down, probably a lot further down than they wanted to, with the understanding that they were only going to get a few paragraphs, max. And I know that there were some departments that were more of a favorite of the speechwriters than others.

My former boss, Cody, tells a story about maybe somebody in the White House staking out a spot outside the bathroom during the writing process. If he would come out of the bathroom, the person would try and corner him and get him to add something into a speech. He would get gifts. He got a coffeemaker from the national security staff [laughter] to try and get something in. People would use all kinds of methods to get their piece in. Sometimes it would work, sometimes it wouldn’t. But I think everybody knew that their space was just going to be so limited that they would have to be pretty focused. Nobody was trying to make half the speech about energy.

We’ve touched a couple of times on the national security dimension. Is it the case that that’s a kind of wholly owned subsidiary of the speechwriting process? Are those guys so specialized that they run their own show, or is everything all knitted together?

That was when everything was pretty separate. We always had at least one dedicated foreign policy speechwriter, and that’s just because it’s a lot easier to operate if you have one person do that. You need to be on “high-side” [secure] email. You need to have a level of security clearance. You need to know the National Security Council staff, which is a separate thing. You need to have relationships with the State Department and places like that. And so it was just easier for one person to do most of that.

I wrote a couple of foreign policy things, and the language is so delicate. You’ve got to think about how something is going to translate. You have to think about the history of another country where people are going to be hearing something. One line that might seem innocuous in the U.S. might not in another place.

A lot of foreign policy speeches come off as a little boring, but that’s because if you get too lively, you might accidentally spark something. I was not jealous of the foreign policy speechwriters [laughter] because it was a high-wire act every time. It was easier to have somebody who had done a lot of that just keep doing it.

And those people were dual-hatted? They were on the payroll of the National Security Council staff at the same time, or were they on the speechwriting staff but just happened to be a specialist?

I don’t know exactly where. I know they had both email addresses, maybe just NSC [National Security Council]. I’m not sure. But in our speechwriting office, they were typically the deputy director of speechwriting. I was the deputy director for about a year, but that was unusual. When I left, Terry Szuplat, who was the foreign policy speechwriter, became the deputy.

Are there any speeches when you’re still in the research position, any particular speeches that we should pay attention to or that you remember as having a special influence?

My favorite was the speech after Gabby Giffords was shot in Tucson. Cody Keenan wrote that speech. One of the people who got shot was this girl named Christina-Taylor Green. She was nine years old, and she was born on 9/11 [September 11 attacks]. We were trying to figure out how to eulogize each one of the people who was killed, and we were going to finish with her.

I did research on her and found a book at the Library of Congress that was called Faces of Hope. It was about a bunch of children who were born on 9/11 with wishes for their lives next to photos of them, and she was in there. They were wishes like, “I hope you learn to sing the ‘National Anthem,’” and I hope you do all this stuff. On the back of her picture was, “I hope you jump in rain puddles.” I found that book and saw that quote and immediately knew. As a researcher, sometimes you know that something’s going to end up in a speech. It was not just because it was tragic, but also because it could give—Obama liked to finish eulogies with a call to action and some purpose. I figured he could use that, especially as there were a lot of citizenship hopes and more patriotic things.

What he ended up doing was basically a five-minute conclusion where he jumped off that and made the point that we need to build a world worthy of kids like her, not just saying how sad it was but also saying here’s what we need to take from that and do moving forward. Whenever a little piece like that can end up bringing it home, that’s your goal as a researcher. That was my favorite piece I found.

In relation to this, I can imagine there being circumstances where you’d be concerned about the President’s ability to deliver something without breaking up.

Sometimes he would. I remember especially around the Newtown shooting [Sandy Hook Elementary School shooting in 2012], he couldn’t really get through that stuff. Generally, he was incredibly good at compartmentalizing everything and not breaking up, certainly not as much as I would or somebody else would. But, yes, I think being President is really hard, and you have to give a lot of bad news, and you encounter a lot of tragedy. You must have a way to cope with that in a better way than most of us do.

But you don’t remember ever having to dial back the content of a speech to make sure he could get through it?

No. This is a recent thing, but I helped with a speech recently on—I think it was the 10-year anniversary of Newtown. At the end, we listed the names of all the kids who were killed. I was working on this. Cody, his former head speechwriter, read it and he’s like, “I don’t know if he’ll be able to go through this, but let’s give it to him and he can make that decision.” He ended up getting through it. So a lot of times, you didn’t preemptively do something. But if he would say, “I just can’t. I’m not going to be able to do this,” then you’d edit it out. And I think he did say that for some Newtown speeches.

Well, I’ve got a whole slew of topics. And since you mentioned the Gabby Giffords shooting, as I recall, the little girl wasn’t just there in the shopping center randomly but had been taken there because she had already indicated an interest in civics, was perhaps a future officeholder, a future leader cut down at that young age. Unfortunately, there are other shootings. Newtown you’ve mentioned. Fort Hood [shooting in 2009] was one of the first that the President had to encounter. Obviously, Charleston [church shooting in 2015]. I hate to read them all out. Sadly, does it happen so often that there becomes a bit of a template for putting those speeches together?

Yes, absolutely. My boss, Cody, wrote a whole book about the Charleston speech that talks about these in general. But, yes, unfortunately, there is a template. You start with a piece of scripture usually. And then the way Cody describes it, you speak to the front row, so you speak to the family. Then you speak to the people in the audience, telling the person’s story, telling the story of the people who died. Then you speak to the people beyond the venue you’re in, and that’s where you usually draw a bigger lesson from what happened or ask people to act in a certain way based on what happened.

It gets a little routine, as sad as that is, to the point where before the Charleston shooting, which came toward the end of President Obama’s tenure, he initially was not going to go speak. He’s like, “I have nothing else to say. I’ve done this so many times. I don’t want to do this again. It’s not making a difference.” He decided ultimately to go, but his frustration was, We keep following the same thing. I keep going out there. I keep talking about this. It happens again. I do it again. So there was definitely some fatigue there and a little frustration.

How did that President and the speechwriting team work? Obviously what he was getting frustrated about, I’m sure, is the lack of movement on the part of congress to get meaningful gun safety legislation passed. I just remember thinking after Newtown, and somebody writing an op-ed about, If it’s not going to happen after 20 first-graders are massacred and their teachers and administrators, then when will it ever happen?

As you say, you’re speaking to the family members of the lost loved ones, and you’re speaking to the community, and then you’re speaking to the country. You’re giving a eulogy, in effect. But how do you tie policy into that, especially as you get towards the end? In this case, he was getting toward the end of the two terms. How do you fold in policy when it’s not getting passed?

That’s a good question. I think towards the end, it was less about specific policies and more about what kind of country we want to be. Because at a certain point you realize, OK, they’re not going to pass anything, especially with a divided government. So what else do we have? It’s less about specific policies and more about asking people to do self-examination and figure out, is this something we’re willing to put up with or is this something we need to do something about?

I thought the interesting thing after Newtown and a lot of these other shootings was, there was not any federal progress but there was state progress. If you talk about the issue and the need more generally, then people go and make their own legislation and figure out how to make a difference in their communities. You don’t have to prescribe exactly what they need to do. After Newtown we did, and it didn’t work. So later on, I think it was more about a little bit of righteous frustration and anger and asking people to pick up the torch because Congress wasn’t going to do much.

I have to go back and read Cody’s book. But the President breaking into the spiritual “Amazing Grace” in Charleston: is that the sort of thing that is completely ad libbed? Or in the speech that he had as a text, did it write out the lyrics of “Amazing Grace” and he, just at the moment, was inspired to begin it with a tune?

Cody has a great description of this, better than I can do it. But from what I remember, it was in the text. But as he was getting off the helicopter or off a plane in Charleston, he turned to the people there and said, “I think I might sing it if it feels right.” So maybe six people knew that he might be about to sing it at the end of that speech. He paused for 11 seconds or something and then sang.

I think it was you talking about his connection to the audience and feeling like he could feed off of them. That’s an example where if he felt that it was right, he could make that decision in the moment, whereas I think if he had gotten a different reaction from the audience, he might not have done that.

For people who read this decades from now, watch the film because you can’t see—obviously, the camera’s focused on him, so you cannot see the crowd out in the audience. But there are a number of people on the stage, primarily clerics and primarily black clerics, who, when they realize what he’s doing, they do call and response and join in.

Yes, they start the drums and it becomes this—yes, it’s a song.

Yes, it’s a performance in a really moving, poignant way.

Yes, one of my favorite speeches he’s ever done.

Was he always good at reading an audience?

I don’t think so. I’ll have to send this to you, or maybe you can get it from the library. Once a 16-year-old girl wrote to him and said, “I’m running for student council secretary. Can I get some tips for public speaking?” He gave her this list of 10 things, and practice was on there twice. He said, “The first 50 times I spoke, I wasn’t that good.” I think he was always pretty good, but just like anything, it took practice. I go back and watch the 2004 speech, his first big one at the convention. He’s speaking really fast. You can tell he’s nervous. So even after that, he got better with practice and with repetition. You see that evolution.

He didn’t actually rehearse speeches very much at all. They had to pressure him to do it for State of the Union. That was usually his one time when he rehearsed. I know in the campaign before the Jefferson-Jackson Dinner in Iowa, he had to memorize it. It was on a round stage and there was no prompter or anything.

And a time limit, as I recall.

A time limit. The night before, somebody was walking by his room, and they heard ESPN [Entertainment and Sports Programming Network] cranked up really high. It was because he was in the bathroom rehearsing the speech. He didn’t like to rehearse, and the later it got, the less he needed to rehearse. He could go up there and read something for the first time and do it pretty well. But that’s just because he had done it thousands of times.

Do you know why he didn’t like to rehearse?

I don’t know. I’m not sure. He’s such a competitive guy. I think he was just like, It’s game time. I’ll do it when it’s game time. He has that confidence.

We always talk about the first debate with Romney. I’m skipping ahead a little bit here, but the first debate with Romney in the 2012 reelection was famously not a very good performance by him. Do you think that was part of the problem, a lack of rehearsal time?

I don’t think so because they actually did a lot of debate prep. That always happened for a week before every debate. Debating and actually answering questions from the press is not his best format. He was very good at speaking. But sometimes when he was answering a question or in a debate, the professor side would come out, and he would give an answer that was too convoluted, too long. It didn’t have as many punchy lines as you’d want. He would try to do some speeches like this too, and we’d have to pull him back. But, yes, it wasn’t his best format.

I think as a law professor, he wanted to do justice to both sides of an argument, to explain it more fully, to not take a shortcut just because he could. Sometimes that worked. In a discussion with people, he was usually pretty good. If it needed to be done quickly, it was not great. I think part of that was he was just not—He didn’t like rehearsing. He rehearsed the debate, but he didn’t like it, and he wasn’t naturally good at it.

We touched on this earlier, but let me ask it more directly. He liked to ad lib in speeches?

Occasionally. If he was really feeling it with an audience, if he was getting energy from them, if they were really enjoying it, he would. The nice thing was that he would usually ad lib and then come back to the same spot on the prompter where he left.

For speeches usually when I would travel, I would be standing next to the teleprompter operator, who was somebody from the military and the White House Communications Office. I would tell them, “Scroll it. Stop it here. Keep going.” And whenever he would ad lib, we would sit right there because he would usually come back to it.

I know Joe Biden is very different. If he ad libs, sometimes he’s skipping ahead to the next section [laughter] so you need to just keep going. But he made our job easier in that we didn’t have to go search out for it.

What about press conferences? Were the speechwriters involved in preparation for press conferences?

We usually were, yes.

How so?

Are you talking about when he would go in the briefing room and give a statement, or more of a formal press conference?

Let’s do both because I’m not sure that I know who has the action on the President’s words in those settings.

He would usually do an opening statement, and so we would write that about whatever the issue of the day was, why we were doing the press conference. Then the communications and the press teams would take over the preparation for the Q&A. They would have a list of reporters and have it ready for him. So we would do the first part, which would be pretty short, and then they would do the hard part.

What about the role of the press secretary in speechwriting?

Not very involved. I was kind of surprised when I went in the White House because you think of that person as the main communications person. But press and communications were more separate than I realized. A lot of times the press secretary was getting ready for their briefing. In my experience, the press secretaries were more about figuring out, OK, what’s the administration’s position, and what’s the best way to communicate that? The communications directors were more about setting that message and coming up with, Here’s what we want to say, and then working with the press secretary to get it out. And this is probably being way too simplistic. There wasn’t as much coming up with the message on the press secretary’s part.

What about the Congressional Liaison Office? I’m assuming the director is one of those 20 people you mentioned who are circulated on things. Did you find that they were heavy-handed on speeches?

Almost never, no. The heavy-handed people would be the policy experts, the David Axelrods of the world. But the congressional people had way more things to do [laughter] than edit our speeches, so they did those things.

We mentioned that you’re writing now for Obama and did for the midterms of 2022. How about the midterms of 2010, speeches that the President was giving out on the stump for candidates?

Then, as we know, famously, a shellacking took place for the President’s party, and he used that terminology in going out and speaking the next day about it. How do the speechifiers cope when they’re hoping for a good outcome and that outcome doesn’t happen? How do you deal with the other side of it?

The interesting thing about the structure in the White House is there are the commissioned officers that you know about—the assistants, deputy assistants, special assistants to the President. And then there were the rest of us. I became a special assistant toward the end, but during the 2010 midterms I was not. You’re not allowed to work on political stuff. Our head of speechwriting and deputy director would be the ones writing the political stuff. We couldn’t legally really be involved in that. It was almost like being back before I was working for him, just watching this stuff happen. I heard about it. We talked about it. But I wasn’t writing any of it.

I remember sitting in the press secretary’s office watching those results come in and seeing how terrible they were. I don’t think it was a huge surprise. In some ways it was, but I think they saw it coming a little bit. One thing I remember after that, when it was clear that we weren’t going to get anything else done, was there was much more of a focus on the pen and the phone and things that he could do by himself.

“Pen” as in executive orders.

Executive orders, “phone” as in using the power of the presidency to bring people together and move things. From a speechwriting perspective, it was a little—in some ways it was nice because you could use Congress as a foil: They’re never going to do this, so here’s what I’m going to do.

The downside was that the things he could do were very limited, and we ran out of the big ones pretty quickly. It was a challenge for speechwriters because the action we were taking wasn’t always the most inspiring or made the biggest difference, but it was all we could do.

Prior to that, though, you have ACA [Affordable Care Act], so that’s obviously huge because that’s the main focus of the campaign in 2008. And then I also wanted to ask you about signing statements. I’m not sure I’d even known about signing statements before they became a thing in the Bush 43 [George W. Bush] administration.

Is this when he’s at the table and he’s—

Yes. Correct me if I’m wrong, Russell, you’re the presidency expert. But wasn’t it the argument of the Bush 43 administration that signing statements had, if not law, some sort of force, as they supported what the President was signing?

Right. Basically, an interpretation of how they intended to execute the law as they signed it, which was arguably a form of line-item veto within a piece of legislation. There were exercises in signing statements before but nothing like what happened under the 43rd presidency.

Right. Did anything like that ever come to you?

I wrote a bunch of those. I don’t remember having anybody talk about that. It was mostly explaining what the bill was, why we’re doing this, what change it’s going to make, why you should care. But nobody said, “If you write it this way, then that means we can execute it a different way.” There wasn’t that much pressure, luckily.

An event, of course, that sparks a historic speech is the [Osama] bin Laden raid. I think everybody will remember hearing the President was going to speak that Sunday night, and seeing him walk into the East Room, and hearing the people outside chanting, “USA, USA.” What was that like? Where were you?

I usually felt like an insider because I would know things were happening before they did, and I would see drafts before. But I got that draft from Ben Rhodes, along with 30 other people on the drafts list, an hour before he spoke, and it was a complete surprise. I was at home. I was in my living room. That was something where—you realize that some of this national security stuff is kept very tight. Even those of us who were in the building had no idea it was going on. That was one of those times where it was just a complete surprise.

Ben Rhodes had written that draft?

Yes. I think he had been brought in, I don’t know how early in the process, but he had to do a pretty quick turn on that one.

You said a couple of times that if you wrote a speech you would travel. Tell us about that. Do you have any memorable reflections on trips you made?

That was always fun and a little stressful as a speechwriter because you would get edits the morning that you were leaving. But then he had a plane flight, and he would want to look at it again. We’d get on the plane. He would have a hard copy up in the conference room where he’d be playing cards or hanging out, and he’d be marking it up. Sometimes he would call you in, sometimes he would come back to where we were sitting and go over a couple of final edits. Then you would have to make those changes and get them sent ahead to wherever we were going. For some reason, Air Force One had the worst computers and the worst internet in the world.

Still?

After 9/11.

Yes. Maybe it’s changed now. I’ve heard it’s gotten a little bit better. But back then, I would have to log into this computer, pray that there was an internet connection, and then send this thing and hope it got there.

Was that to get it on the teleprompter?

On the teleprompter and to the people who were at the site to print it, because there was always the teleprompter and then we had a binder with the printed speech in it in case the teleprompter broke. The binder had larger print, and it was in sleeves so if it rained it wouldn’t get messed up.

Then sometimes for bigger speeches he would ask for another round, and so you’d have to print it out and go back to him. The worst was when you’d be getting off the plane and might have a 15-minute drive to wherever we were going. He would hand you the last edits and say, “OK, these are done.” He was washing his hands of it. Then you have a little air card that you’re plugging into your laptop to get internet in the middle of Iowa, and you’re in the back of a van trying to make these last edits and send them.

It was always a red flag to me when I would look at the schedule, and there was a 20-minute difference between when we landed and when he started speaking. That was the time I was going to have to use if I needed to make final edits. It was always great if you had some meet-and-greet for an hour beforehand, and you’re like, OK, I’ll be fine.

But the great thing about being a speechwriter is, once the speech is done, you’re done. There was nothing like the feeling of having him give the speech, it’s over, and then you can relax on the plane ride home and have a drink and have dinner. It was never a relaxed flight to wherever we were going.

How much feedback did you get from him after a speech?

After a speech? Usually not a whole lot. Sometimes you’d see him and he’d say, “Good job,” or “I think that went well.” I didn’t get a lot of negative feedback from him. I think he was nice enough to know that it’s done. Maybe he can make some edits next time to fix whatever went wrong, but yelling at me after the fact was not going to change anything. I appreciated that.

So you don’t have any memorable dressing-downs after any speeches.

No. A friend of mine was a speechwriter for Biden until a few months ago, and he has many stories of that.

Currently? Biden as President rather than vice president?

Actually between vice president and President was the one story he told me. Apparently Biden, after the speech was over, brought him to the back of his plane and was dressing him down for two hours about what he wanted to do differently and what went wrong. Anyway, thankfully, I never had that experience.

That has to be a flaw in the process, right?

You’d think so, yes. That’s the thing. If the President didn’t read something and then he didn’t really like it, I think he recognized, That’s on me. And if he had read something and we’d gone through multiple edits and something didn’t work, that was because it just didn’t work. We both had had a hand in it. We maybe guessed wrong on some audience reaction, and it just didn’t happen.

He’s a speechwriter himself. He’s the best speechwriter we had. He would tell us that sometimes. [laughter] I think he recognized that if he had all the time in the world, he wouldn’t need any of us. So I think he understood. He gave us a lot of time. He understood the process. He understood how sometimes things work and sometimes they don’t. I think some people think speechwriters are magic. He knew that we weren’t, and so there was some sympathy there.

What about the director of the speechwriting operation? Are you getting after-action reports from them about either success or failure in a speech?

Again, I’d get more feedback on the front end, edits and things like that leading up to it. After action, I can’t think of that many speeches that went very differently than we thought they would go.

Do you remember any instances?

Not really. There was an economic speech early on where he was really dressing down Paul Ryan’s budget, and Paul Ryan happened to be sitting in the front row of this speech. That was not a good thing, but that was more of we didn’t have that information. I can’t remember too many where we finished and thought, “We made a mistake somewhere in there.” If it didn’t go over well, it was almost just bad luck.

Your comment about Ryan leads me to ask about the degree of input that you had for setting. Is it the case that you’re basically being given a set of instructions about the reality on the ground when you arrive? Or do you have some influence over what the setting on the ground is going to be like once the President arrives?

That’s a good question. Almost no influence. We had somebody usually in the White House who was the director of message events, and so they would be the person who would set up and say, “OK, we need to talk about health care this week. We’re going to go to x place because—” There could be different reasons for it. But we would usually be told, “Here’s what we’re talking about, here’s where we’re talking about it.” Then you’re off on your own to figure out the best way to do it.

So it’s somebody else’s job to determine where the lectern is, the staging, who’s going to be on the stage with the President, and so forth? But typically you’d be instructed about these things.

Yes, right.

Just one circle back that occurred to me for State of the Union, and that is the guests, usually with the First Lady but up in the gallery. Who makes those choices since the Reagan era? But in Obama’s case, who made those choices? Is that mostly the political people? And once those people are chosen, are the speechwriters informed? Say, We’re going to have these five guests, and this is what they’ve done, this is why politically we’re picking them, and so be sure to have a few lines about each of them.

The answer about who picks them, I don’t really know, honestly. In my experience, some of them were people that were picked by other folks in the administration. One piece of my job early on that I haven’t mentioned is that I would read through a lot of the letters he got from people who wrote in. That was some of our best material because we could quote from them. We could bring people there. We could talk about how this was having an impact on somebody’s real life, and so we worked closely with the Correspondence Office.

Sometimes if you found a great letter, a great quote from somebody, you’d get them in the box for the speech. So some of it was us suggesting people, some of it was being told here’s what we have to do for a political reason, or somebody in the communication shop could make that decision and we’d end up finding a way to mention them. I don’t think we had to mention everybody. There were often people in the box who didn’t get mentioned, but it was always a good way to—we wanted at least a couple of those in every State of the Union.

Do you recall any that you said, “Oh, great letter, what a story, how poignant,” and then that person was chosen?

I’ll have to keep thinking about that. I don’t know exactly.

Now that I’ve brought this up, I’ve always wondered about this. That seems to be a much more modern approach to presidential speechifying, and I use this example. What if Lincoln in the Gettysburg Address had begun to point out wounded soldiers from the Gettysburg Battle, what a different speech that would be and probably not as good.

Did you ever pause to think about I’m sure this can be really helpful because it’s an actual example of someone hurting and needing help from the government and policies. Or of someone who was hurting, and then, because of our policies, is no longer hurting. It does seem that presidential speeches have taken a turn towards that. Did you ever ponder that and what it meant for presidential speechwriting?

I hadn’t really thought about the shift that much, but it makes sense. I think some of it comes down to a little bit of a loss of presidential credibility. This is just my opinion. I feel like if FDR told you something was happening, a lot of people trusted that it was happening, and it was happening the way he said. I think especially around health care, for example, we needed to make the argument that something needs to change, that this current system isn’t working the way it should be.

We used a lot of letters around health care because it was much more credible for somebody to say, “Hey, I almost lost my house because I got sick, and I don’t want that to happen to other people,” than it was for President Obama to just stand up there and say it because half the country wouldn’t necessarily believe him. Maybe half the country wouldn’t believe that the person in the letter is real, but it was an attempt to say, Look, don’t take my word for it. Take the word of somebody who is probably a lot like you and is dealing with this thing that you might have to deal with someday.

That’s a really interesting response that I had not considered.

Could be wrong. [laughter] I don’t know.

It’s fascinating.

What about relationship to the vice president and the First Lady? Were you involved in speechwriting for the two of them?

When I was a research assistant, I did some writing for the First Lady because Sarah Hurwitz, who was her chief speechwriter, needed some help. That was my first real experience working with a principal, and she was great. She had a very different approach from the President, very different voice. She would want speeches two weeks in advance, and she’d want to rehearse them with you. She had a much warmer, more emotional, more personal voice, so I actually really liked writing for her.

She had a small team, and you felt like you weren’t just in there to get five minutes of the President’s time. You could actually spend a little time and hear some stories and get more material for a speech, so I liked doing that. It felt like the West Wing was where I had started and where I wanted to go back to.

The vice president had his own staff, and they were pretty separate. I knew those speechwriters, but we didn’t work together all that much because they were also doing different events. So it wasn’t like we were comparing notes on what they were saying at the same event.

I’m trying to think back. You had one woman as a speechwriter, is that correct, in the original batch?

The original batch, yes, Sarah Hurwitz. Then the speechwriting team got more diverse as we went. I think this was partially a sign of the times. But it started out, we were all white men and one white woman, which is not really what you would want for the first black President.

It also raises the question about the issue of race in this presidency, which is a really unsettled field for examination. I don’t even know how to ask the question other than just throw it out there to get you to reflect a little bit on how the President dealt with the issue of race in his speeches and in his own daily life with his staff. It seems from the outside at a distance that it was sublimated, that there was not much attention to it, but I wonder if that’s true.

Just the bigger picture, I think it was intentional that he didn’t want his presidency to be about—his presidency was always going to be about race because he was the first black President. But I don’t think he wanted to be seen as the President for only African Americans.

I think he was always very sensitive about how to talk about race. The times when he chose to talk about it, it was very intentional. I’m thinking about Trayvon Martin’s killing, a lot of times when he would go in front of black audiences. He didn’t want people to listen to him and feel excluded, like he was talking about somebody else who wasn’t them. I think about the race speech. It was a message to black audiences, but it was also a message to white audiences. When he did that, it was educating each side a little bit and maybe trying to find a little bit of commonality in between.

Race was the most fraught issue of his whole presidency, I think, and I feel like he was caught between feeling an obligation to the black community for supporting him so much—feeling like a representative of that community—but also realizing that he was the President of everybody else and trying to hit that balance. It must’ve been incredibly difficult.

Practically, some of my favorite speeches I wrote for him were to black audiences because I knew that it was—The best speeches are speeches that only the speaker can give. Mary Kate Cary always says that you should be able to cover up the top of a speech and know who said it, where they said, and when they said it. I wrote his commencement address at Morehouse College.

We have that in the background materials.

Yes, and that was fun. I showed up to get his thoughts on it, and of course I had some thoughts of my own because we didn’t want to go in empty-handed, but they were not the right ones. [laughter]

What were they, do you remember?

I don’t remember. I’ve just forgotten those. But I knew that it was going to be special because this was a graduating class of black men, and he was the first black President and somebody who could talk to them in a way nobody else could. When he was giving us guidance for it, he said, “Here’s what I want to say. Some of this stuff you may be uncomfortable writing. But just remember that I’m the one saying it, not you.” That gave me permission to try and inhabit him a little bit and try to be a little bit more edgy than I might’ve been on my own.

Then he, of course, took it and made it a lot better and said some things that I never would’ve thought to write. I really liked that because it was one of the things that made him unique and special, and he was talking to a group that probably saw themselves and saw the presidency differently because of him. I always felt like a middleman between him and his audience. I wasn’t necessarily adding that much, but I was helping connect them a little bit. I really liked doing those speeches.

Was there ever an instance where you felt like you were getting chastised by him because you weren’t getting him right on race? I can envision a set of circumstances where a black President would come to an all-white staff and say, “Come on guys, you don’t get this.” Do you ever recall that happening?

This is where he was a good boss. I think he understood, Look, there’s some stuff you’re just not going to get and you can’t get. So get me a little bit closer, and I’ll finish the job. That was true because, look, I could talk to as many people as I could find, but I was never going to fully understand what it would be like to be him or to be somebody like him. I appreciated that.

You’ve said all the way through, “a good boss,” not dressing you down, or I’m presuming you didn’t witness that. So, “no drama Obama” is what you saw? Anything that was ever outside the “no drama Obama” label?

You read about this in his book and hear about this from others. There were issues, obviously. But I think nothing rose to the level of some of the issues in other administrations. So it wasn’t that there was no drama. It was just that the drama was, I think, a normal level of drama [laughter] and nothing that led to indictments or enormous scandal and things like that.

That is certainly well known. Can I circle back to Michelle Obama? You said you enjoyed writing for her, totally different approach from her husband, the President. One was that she wanted to have things ahead of time and practice. Did she call you in one-to-one or with Sarah and talk to you about what she would want from a particular speech?

I’d usually go in with Sarah and with a couple of her staff, her chief of staff, maybe her communications director. And whenever we were meeting with the President too, it would not just be the speechwriters because a lot of times the communications people would want to know, OK, here’s the angle he’s going to take, here’s how we should prebrief the press, maybe some other opportunities we can find around this topic. So it was always other people. Once you got down to individual edits, then sometimes it would be just you and them, but for the big idea meetings, it was a bigger group.

You said that she had, of course, a different style. She’s a different person and a woman and one who doesn’t have any authority, has no official authority or official title. You said her speeches tended to have more emotion in them.

I think her lack of an official title was actually an asset in a lot of ways. Again, just my opinion, but I feel like people are naturally suspicious of politicians and why they’re doing what they’re doing and how ambitious they are. She was seen as somebody who this just happened to. She married this guy, and then he ran for President. She was obviously on board, but she didn’t make this decision herself.

I think her power—and you can see this in a lot of the convention speeches—has always been to say, “Look, I’m going to talk to you as somebody who knows this guy really well but somebody who’s also like you, somebody who’s not a politician, somebody who would never be up here unless I got thrown into this spot.” I think there’s a lot of power in that because as soon as somebody starts running for office, half the country is probably going to be really suspicious of them. But with her, she could say, “Look, I’m going to talk to you as a mom. I’m going to talk to you as a wife. I’m going to talk to you as somebody who cares about this country and who’s worked to help people in different ways.” I always thought that gave her a lot of credibility. She could talk about things that he couldn’t talk about sometimes.

I want to ask a political science question that we debate both as political scientists and then when I go to these conferences or there are panels about First Ladies. What some scholars have done—and I love that you mentioned power, her power. Some people ascribe to First Ladies what they call “soft power,” which tends to be the more emotional or, I’m like you and I’m a mother and I’m not elected but my husband is, but let me talk to you person to person, woman to woman. So it’s diplomacy, it might be something in the arts, something related—policies related to women, children, military families, the things that we know that Mrs. Obama cared about.

Then the “hard power” is what the President is exercising with the military or economic sanctions and things like that. I’ve talked about this, and then I’ll sometimes have a historian or political scientist, particularly feminists, say, “There’s no difference. Power is power,” which you could make an argument for. But you just said “power,” and yet you were working for someone who had the hard power, if you choose to delineate it that way, and then someone who had soft power. What’s your vision of that?

I don’t know. In a certain way, I’m with you. I don’t really see a difference in those two things. I think you can have power with different audiences and for different reasons. I thought it was interesting for her. She obviously took on some issues that were more traditionally in the First Lady’s wheelhouse with nutrition and military families and things like that. But I was also really impressed every time she got into the more traditional political realm, like during the campaigns. She could talk about the issues in a way that she was experiencing them as a mother, as an ordinary citizen. Not too ordinary, but she could say, “Is this really the country that we want for our children, or is it this?”

I thought that was always really powerful because people could see themselves in her more than they could see themselves in Barack Obama. Whether that’s hard or soft power, I don’t know. But it was a different kind of power than he had, and I think it was equally effective sometimes.

Did she ever mention to you the concern that she might have, you just mentioned, about the country she wanted and we should want as Americans to live in? We know she came under criticism in 2008 about the so-called “terrorist fist bump” and that this was the first time she was proud of the country. Did she ever bring that up or say, “Let’s watch this, let’s be careful not to push that button in this speech”?

I joined the campaign right around, maybe after that happened. And there was this big project in her office to show people a different side of her. People’s thoughts about her were trending towards “angry black woman.” That wasn’t necessarily realistic, and that wasn’t going to help the campaign, so they wanted to pull it back.

That’s when Sarah Hurwitz, who’s an incredibly talented speechwriter, came in to try and help her tell more of her story and reveal a little bit more of herself. I think she was pretty hesitant to do that for a long time. You saw that in the White House, when she would go on Jimmy Fallon and dance with him, or when she would go on Sesame Street, or plant the garden outside, or do jumping jacks on the South Lawn. There was a lot of that.

I was always impressed with her team because they took her from somebody who was getting a lot of criticism to one of the most popular public figures in the country in a few years. And I think a lot of it was her. They were showing the world more of her, but I’m sure that was always in the back of their minds. They didn’t want to slide back into that, but they also wanted her to be true to herself. I think once you do have that popularity, then you have a little bit of permission to get a little bit more pointed and to be a little more political. But you have to build up that goodwill first.

Was he comfortable or uncomfortable using her in his speeches?

It would depend. Sometimes we would put in a joke that he would cut about her, but then sometimes he would ad lib something. He was always very sensitive about how to use the girls in any kind of speech. With her, it was a little bit easier. I don’t know. Just like any spouse, he didn’t want her to be mad at him. [laughter] We just had to be careful not to—we could joke about it but only to a point.

Right. And if he was going to make a reference to the girls, it was usually something he would insert or would you try out things?

We would put in lines about “my daughters,” what he would want for his daughters and everybody else’s. I think that’s about as far as we would go.

But not any more direct references to things.

No. I think he was just really aware of their privacy.

Gotcha, OK. Let me do this if I may. In the timeline, there are a lot of speeches, particularly in the first term. Let me just mention these to see if they provoke any thoughts. If they don’t, just say, “Don’t have any recollection of that.” The Cairo speech.

That was Ben Rhodes. I think I did some research for that but wasn’t terribly involved in the draft.

Ted Kennedy’s eulogy?

That was Cody Keenan. He had worked for Ted Kennedy for a long time. I did a lot of research for that, stories from his life.

Any recollections of the process leading up to that?

I know Cody took that more seriously than almost any other speech because he was close to Ted Kennedy and wanted to do it right.

Yes, so the eulogy, and then just speaking when he passed away. I think the President was at Martha’s Vineyard, and he came out and spoke.

Yes, I think that’s right.

Nobel Peace Prize in Oslo?

That was the only time I did research directly for the President because he wanted to do a lot of writing himself on that one.

How did the assignment come to you?

I think he asked Jon Favreau or Ben Rhodes or somebody for a lot of [Friedrich] Nietzsche, [laughter] for a lot of philosophy and speeches about war. So I put together a binder for him, and I think he went through it. He didn’t write that much himself of the first draft.

You might’ve heard this from somebody else, but they basically stayed up all night on the flight over to Oslo and rewrote the speech. It was a little crazy. Everybody else had gone to sleep on the plane, and Ben and Jon Favreau and the President were up just rewriting it together right before it got delivered. If you talk to Ben or somebody like that, they can tell you the whole story.

You know this. It was such a weird speech because he was being given the Nobel Peace Prize at a time when America was at war. So he wanted to get in this idea of just war and figure out is war ever justified, under what conditions, that kind of stuff. It was more of a philosophical speech than anything else. I think he engaged with it at the last minute, and it sounds like a crazy flight.

That was in your wheelhouse, Nietzsche?

Yes. I was pulling out a lot of philosophy.

Because you majored in that.

Well, yes, I read a little bit a long time ago.

Larry Sabato doesn’t do Nietzsche.

No, no. But that was Obama’s favorite philosopher. I’m not sure how many Presidents have had a favorite philosopher, but that was his—I apologize, I think it was [Reinhold] Niebuhr.

Oh, Niebuhr, yes. Niebuhr was Carter’s.

OK, yes. Sorry, I got those two confused.

Yes, it can happen. You wouldn’t want to get those two confused.

No, no.

The eulogy for the miners in April of 2010.

West Virginia.

It’s funny. I saw that, and I totally forgot about that one. I apologize.

I circled Deepwater Horizon. I don’t remember any speeches on that.

No. That was a crazy time, and I’m sure you’ve heard this from a lot of other people, but it just kept going on and on and on. That picture of the pipe spewing oil at the corner of every cable channel all the time was hanging over us. I remember we were in a videotaping session with the President, and the First Lady stuck her head in and she was like, “So, did you plug that well yet?” You talk about the relationship between them! He stared daggers back at her. [laughter] I’m sure she thought that was funnier than he did.

I have a question on that point. How do you present a problem in a speech to the American people when you can’t solve it at the moment?

I don’t know. The way we did it was, we talked about all the ways we were trying to solve it. And I think that’s where Steven Chu got together a crack team of really smart people and tried a bunch of different things. But, yes, I think the only thing you could say at that point is, “We have really smart people on it, and they’ll stay on it until they find something.” But that was incredibly frustrating. There were a few issues in his presidency where you can’t move on until this thing gets fixed, and that was one of them.

I guess you didn’t have anything to do with the bin Laden speech because you didn’t know about it.

No, no.

The Giffords speech, you said, was one you had worked on.

Yes, I worked on that.

Do you have any further recollections on that one?

No, nothing that I would share, sorry.

So you become a speechwriter in full force in June of 2011. How did that come about?

A couple of our writers left. Adam Frankel left the White House. He had been with the campaign for a while. And I think Jon Lovett left pretty soon after. So there was, all of a sudden, a spot, and I moved up to one of those spots, and we hired somebody else.

Hiring speechwriters was always tough because you’d have to bring in people who didn’t know President Obama that well. A lot of times we would audition people from the Cabinet agencies and do blind writing tests. We’d give them a prompt, and they’d write it. Then we took the names off of them, and everybody read and rated them.

We found some fantastic writers that way. It was a lot harder to hire people than I thought it would be. But, yes, I was lucky to be able to again write small things, and then bigger things, and then eventually slide into the spot.

You talked about people leaving, and some people having to stay up all night on a flight to Oslo. We hear from so many people about how enervating working at the White House is, up early, staying up late, maybe being there on weekends. What was your life like up to this point? And then when you get a promotion to being a full-fledged speechwriter, what was it like for you?

I always tell people that, at least in my experience, there were a lot of people in the White House in their early to midtwenties, a lot of people who didn’t have spouses or kids or a lot of attachments. Then there were people in their forties, who maybe had older kids and who were doing this as almost like a public service stint for a few years. There weren’t that many people in the middle, not a lot of people like me now with two young kids, because it was a crazy schedule and you were never really off. I didn’t have to make the really early meetings in the morning that the senior staff did, so I would go in maybe eight-thirty and then be out of there around six, six-thirty.

But then speechwriters can work anywhere, and a lot of my best writing got done between nine and midnight. I really like the quiet, and nobody was bothering you, and that’s when you’d see things a little bit more clearly.

You’d be in the office for that?

No, I’d usually do that at home. Of course, now I’m still a speechwriter, but I can’t stay up that late because I have to get up early, so I don’t have that luxury. But, yes, it was a grind. I think that’s why people burned out. I lasted five years, but I hadn’t been on the campaign all that long. Some people left before me, and I understood why. I think a lot of people in the older set also made a deal with their spouses that they were going to do this for a certain amount of time and then leave. So there was a lot of this predetermined time.

We hear this reference occasionally, an old historical reference to “Rose Garden rubbish,” the stuff that you have to churn out. How difficult is it to stay on top of just the day-to-day business of cranking speeches out for every little occasion?

It was tough. And, like I said, ideally you’d have one speech a week, sometimes two if they were smaller. Luckily, you had to have a certain amount of people in the speechwriting office because you wanted everybody to do their best on each thing. Sometimes it was tough because you would send it to the President the night before, and you’d get it back with no edits. I’d have to ask his staff, “Did he actually read this?” Sometimes the answer was, he didn’t. A lot of times these were sports teams or some lower-level thing. I always liked it when I put a joke in one of the speeches and he laughed because it was the first time he’d read it, [laughter] when he was actually up there delivering it. It also made me a little worried.

But, no, it was a ton of volume. And that’s where a lot of what Dan Pfeiffer and other people did was say, “Look, we’re talking about too many different things too often. If you talk about five different topics in a given week, none of them are going to break through.” Especially when Dan came in, we got a little bit more disciplined about, OK, this is going to be the theme for the next couple of weeks. We’re going to find a few different ways to talk about it, then we’re going to move on to something else. But at the beginning at least, there was so much to do and so many different topics to cover that we were just doing way too much on way too many things.

What I’d like to do next, with Barbara’s permission and yours, there were four speeches that had been flagged to our research staff that you’d been involved with. It would be really interesting—I don’t want you to do a line-by-line exegesis of these things, but just take a look and see if these prompt any particular memories about the process of writing or what you were thinking as you were producing the individual speeches.

I’ll see if I can pull any bigger points from this because these are a little specific. The first one is his eulogy for the victims of a fertilizer plant explosion in West, Texas. This is one of those things where I don’t know what rises to the level of a President going and giving a eulogy, but this one did. It was interesting because it is a very, very small town.

I love doing speeches like this. Obviously not a great topic, but this is where, as a speechwriter, I would talk to a lot of people on the phone. For a community like this, you really want to understand what it’s all about, what makes it special, what is it about the people who died that made them unique, and just understand. I think the President’s job in a case like this was to say, “Look, you’ve probably never heard of this little town. Here’s why you should care about it, and here’s what we can take away from their example.” There was a lot of just immersing myself in who they were.

How do you find these people?

A lot of times it’s the people who are doing advance, who are prepping for the visit and have contacts there. You ask them, “Hey, if I really want to understand this town, who should I talk to?”

One thing I haven’t talked about is how, as a speechwriter, you spend a lot more time on the phone than I ever expected. Your job is to almost be that middleman between the President and the country, describing what these other people are feeling. So it’s not really about you. It’s almost more about them, so you don’t want to put too much of yourself in there when you could get some good things from other people.

Would these people be alerted that you, a speechwriter for the President, would be calling?

Yes. If we found a letter that we wanted to quote from, I’d have to find the letter writer and get permission. So you became a kind of private investigator. I would look for any connection. If they mentioned that they were a teacher and this was their name, I would try and find their school and contact the school. Then when you finally got to them and you said, “Hey, I’m Kyle O’Connor from the White House,” half the time they don’t believe you. I got hung up on a couple of times. And then you finally get them, and it’s really cool to tell people, “The President actually read your letter. We want to talk about it in this speech, and we’d like to quote you. Is that OK? Here’s where you can watch.” It’s like the first time I heard my words coming out of his mouth: if they hear him tell their story, it’s pretty mind-blowing. So that was one of my favorite parts of the job.

In these instances, you wouldn’t have had a letter from someone, but they would’ve been alerted that you would call. Did you ever get a sense from people that they didn’t support Obama?

Some people didn’t, yes. It’s so funny how real life is so much different from Fox News and Twitter and everything else. People by and large were incredibly respectful and respected the Office of the President even if they didn’t like the President all that much. Especially if we were talking about them because something like this happened, or because we were trying to help people like them, they were much more likely to give him and give us the benefit of the doubt. That might’ve changed since we were in there. I know things have changed a lot. It’s amazing how when you’re actually talking to people, there’s not that vitriol that you get from a lot of the covers these days. It made me hopeful as long as you could talk to people.

The funny thing about the beginning of this is Kyle Matous, whom you mentioned, grew up not too far from there. I talked to him and asked, “What reference could we use that might play well in the room?” He mentioned that this town is known for a Czech pastry called a kolache, so I put that in the speech. It’s not spelled the way you think it would be. I remember we were riding on helicopters to the speech site, and I got a message from the President’s body person who said, “Hey, he wants to talk to you after we land before we go to the venue.” He had been reading through the speech, and he said, “What is this and how do I say it?” [laughter] There’s a picture of me talking to him, and we look like we’re discussing something really serious, but it’s how to pronounce the name of this doughnut. I had called Kyle and said, “Kyle, how do you say this? It’s a really important thing to get this right because I’m going to tell him how to say it.” He told me, and he got it right, thankfully.

You find so many stories for a speech like this. The trouble is how do you use the right ones and not do too many, and how do you make them connect? A lot of the stories that I found, we used towards the end of the speech to say, “This is what makes a town like West special, and this is what by extension makes America special and what we should be grateful for in our communities no matter where we live.”

I wonder about his own upbringing. We have this sense of this young man who was kind of cosmopolitan and had this specific experience, his mother being an anthropologist. But there’s the other part of him, which is Kansas. That piece, I think, tends to be underappreciated by people.

Well, and the Kansas grandparents were the ones that he spent the most time with growing up. When Queen Elizabeth [II] died, he talked about how she reminded him of his grandmother. And in speeches about pay equity and things like that, he would talk about how his grandmother worked for years and ended up getting paid less than people who had been there for a short amount of time.

Part of his power is that he has the ability to connect to so many different types of people. So, yes, he could give a speech in front of a black audience, but he could also empathize with people who were from small towns or from the Midwest.

Well, he’s half white.

That was it. He could make those different connections without seeming disingenuous, like he was just pandering, which for a politician is incredibly powerful.

While we’re in Kansas, though—the Osawatomie, Kansas, speech, which is to follow on Teddy Roosevelt’s 1910 speech and particularly populism. Did you have any role in that one?

A little bit. You’d asked if the speechwriters ever got to have an influence on the location of a speech. That was an instance where—I wasn’t specifically the person who did it, but I think we found that and realized that it could be fun to go back there. That’s where it directly came from speechwriting. I’m sure I was involved. I know I was involved in pulling a bunch of research and ways to tell that economic story. But I’m sorry, nothing specific comes to mind.

That’s OK, just knowing that you all had a role in picking that out for the 100th anniversary of the famous Teddy Roosevelt speech.

A lot of times you’re really stretching with the location connection, but that was cool to be able to actually go back there.

And to go back to the home of his grandparents, go back to Kansas.

Right. Yes, that was maybe the best location for a speech, as far as connecting to the subject, that we could’ve possibly done. We talked about Morehouse a little bit. First of all, it was storming. He was on this big, metal stage, and there was lightning coming toward where we were, so there was a chance they were going to have to pull him off the stage before he got to speak. I had worked so hard on this speech, and I was like, Please, hold off. [laughter] Luckily, he gave it, and then we got right out of there. But the Secret Service, I think, was pretty nervous about him staying on there too long.

You have several references to the rain in the speech.

Yes. Coming back to the idea of calling people out, I found a few examples of people in this speech—like this guy Frederick Anderson, who went back and left, and went back and left, and finally graduated. He stood up, and there’s this famous picture of him. I mean, not famous, but it was on the cover of the Atlanta Journal or something. He’s crying, and it’s raining, and that’s when Obama called him out. It’s really cool to see how a small decision like putting a story in a speech can blow people’s minds a little bit and change their lives a little bit. I always loved doing that.

To that point, you had mentioned earlier that when you were traveling with the President and he gave a speech, you would be sitting next to the military teleprompter runner. So when you had moved up into full-fledged speechwriting, were you with the President there at Morehouse? And where is that? Is that under the podium or off to the wings?

It’s usually backstage somewhere.

So you weren’t able to see audiences when you were playing that role, correct?

There’s always a television monitor there, and you can usually stick your head around and see the audience.

Right. But for something like this, were you still doing teleprompter supervision?

I was, but I also remember being on the side and seeing the audience. So I think for this one I could do both. You can always do that.

And that was going to lead me to another question. After you had done these speeches, you would either go or not go with the President to deliver them but to really hear if he said, “Yes, that went well,” or not. Did you watch in real time if it was on television or some sort of circuitry that brought it into the White House? Basically, my question is, did you go back and watch speeches multiple times to see what you had put in or what the President had put in and how that was having an impact on the audience?

I didn’t really do that. I was always a little uncomfortable watching the speeches that I had helped write just because if something didn’t go exactly right, you’re kicking yourself for it. I would make some mental notes about what I’d want to do differently next time, but I wasn’t a big analyzer of it because in a lot of cases the next speech would be totally different. There are some lessons you can learn from it but not a whole lot that you could directly take.

Just happy to be through it.

Yes, I was just relieved. The other thing about this Morehouse speech is there was some coverage in the press that he was pretty harsh on the graduates. If you read it, he says, “Look, nobody wants to hear how tough your upbringing was.” Just basically, don’t make excuses for yourself. I think there’s probably some truth to that. I think it was harsh within a lot of graduation speeches. But I also think he saw these young men as versions of himself, and I think there were times—and I think he would tell you—that he could’ve gone a couple of different ways. I think part of his mission here was to say, Look, I was in your shoes. I ended up making the right choices after making a bunch of the wrong choices. Don’t feel sorry for yourself. Don’t look for excuses. Just go out and work twice as hard, as your grandmas have probably told you to do since you were born. It’s interesting. I’d be interested to hear how some of the graduates took that and how they think about it years later, not just the press.

Was the immediate reaction of the audience favorable while he was there?

Yes, it was. But, again, I’m also really conscious of my lack of understanding of this community. I think we did our best, and that’s what he wanted to say, so that’s what he said.

One would’ve thought that the Right of the spectrum would be particularly happy with a President saying to young people, “Don’t make excuses. Work hard.”

Yes, probably. I didn’t watch Fox News on that speech, but maybe they liked it. I’m not sure.

The 50th anniversary of the March on Washington was the biggest speech I worked on up until that point and also one of the toughest. I remember writing the draft of it and then sending it to Cody, who was my boss at the time. He totally tore it apart. He was very nice about it. I think he said, “It’s all here, I’m just using it a little bit differently,” which is a nice way of saying, “I’m going to do something completely new.” [laughter]

But this was a fun speech to research because for me, I thought, Let’s find some details about this that people don’t necessarily know. They know about the big speeches and how it looked on that day, but they don’t know how people got there. They don’t know all the places they came from. They don’t know what it was like, in some ways, to be on the ground that day, who these people were, a lot of the people that came. So we did a lot of research and tried to tell a new story, a fresh story covering a very old, very well-known event. That was fun. The other thing was, OK, what lesson do we draw from this?

One thing he talked about was how this march was not just about civil rights. It was also about jobs, and we’re still on that march. So how do we channel that spirit that we saw back then to the problems we’re facing now, and what lessons do we draw from those days to today? It was kind of cool because I was standing behind him on the Lincoln Memorial, and you see it was obviously not as big a crowd back then, but there were still people on both sides. And so you kind of think this is a version of what it must have looked like back then, a crazy venue to be at.

It was a lot of pressure because the 50th anniversary of something like this only comes once. I think it might’ve been a little bit like the inaugural, where we tried to go a little bit too lofty for marble. But it was fun to try and meet that moment, even if we didn’t fully get there. To say, “OK, on the 50th anniversary, what is there to say today?” It was just fun to try and figure that out.

How did you get over there?

We took the motorcade from the White House. We didn’t walk. [laughter] I guess we could have.

You didn’t helicopter.

No, no. It was not that far. It was almost amazing riding in those motorcades because you’d be breezing down a highway and you’re like, Oh, this is great. Then you’d see on the exit ramps these backups of cars waiting because you’re going through. I took a trip with him to San Francisco one time, and we landed at the airport and then went up to the city. It took us 15 minutes. Then I moved out there and did that drive every day on my way home, and I thought, This could take an hour. You miss those days sometimes.

There’s one more here. Oh, is this the St. Patrick’s Day one? Yes. With a last name like O’Connor, I wrote seven St. Patrick’s Day remarks because he would do two every year. One was usually with the Taoiseach at the White House, and then one was in Congress. I put together this research binder when we first started doing them and I was the assistant. We kept adding to it, and it became this whole monster thing with every Seamus Heaney quote and every story about Ireland you could find. By the time we were done, I was desperately trying to find something we hadn’t used before.

That was always fun because my dad’s entire family is Irish, and it was always cool to do a little bit of research on that and feel like I had a little bit of skin in the game. He had the connection back to Ireland and could always make the “O’Bama” joke. [laughter] Plus the White House was always fun that day because it was usually just barely spring. It was feeling nice, and everybody was going to get a Guinness after work. Yes, it was a fun day to do.

Were you a student of contemporary Irish politics, or you just have the culture in your background?

A little bit.

Because it’s complicated.

Yes. Have you read Say Nothing by Patrick Radden Keefe?

Yes. It has a heavy oral history component.

Yes, right, BC [Boston College]. I didn’t know enough back then. I just knew that things had been decent for a while even though there were still issues going on. My wife studied abroad in Ireland when she was in college. I’ve never really been. I’ve been in the airport going to somewhere else. But I want to go back there, especially with our kids, and have fun.

We, as a part of both the Kennedy project and the Clinton project, made trips over there. I met and interviewed Gerry Adams, I guess, twice.

I never realized until reading Say Nothing that he never really admitted to being the leader.

Oh, no. I asked him directly about this, and he said, “No, I was not.” It’s still his straight-up line. But then I also asked another very—I would be forbidden to tell you who it is if I could recall his name, but I can’t—a very senior Irish official directly, and he said, “Oh, absolutely. No question he was a high rank.”

And so you’ve got to wonder, does Gerry really not believe it, or is he just so used to lying at this point that he—

No, I think he believes it. In fact, I think I asked the person this question. He said, “If he admitted it, they would kill him.” It’s serious.

Even now?

Yes, even now. Adams is a very interesting person because he’s very scholarly and congenial. Yet you read this book, and you’re thinking, This is a guy with, evidently, blood on his hands. And if you’re trying to do an interview with him, you have to kind of keep this in mind as you’re doing it.

That probably is what made him such a good leader: he could be out there giving the smooth politician version.

I think you’re exactly right. It’s the 25th anniversary coming up on Good Friday in three weeks.

We’re coming towards the end here. I’ve got just a couple of things. One relates to where we are, Charlottesville. In August of ’12, the story we heard was that the President’s team had reached out to say he wanted to come to Charlottesville and give what was by then an opening kickoff maybe for the campaign and that the thought was maybe the amphitheater on the main Grounds. Again, the story we heard was that the University said, Oh, the date you’re asking for is the first day of classes, and we would have to cancel them for security. We don’t really want to cancel the first day of class for the fall term. He came into Charlottesville, but he gave the speech down at the Pavilion on the [Downtown] Mall.

Was this in ’12, or was this during the first campaign?

Twelve.

I’m forgetting about this, sorry.

August of ’12. Then maybe the answer is “I don’t remember.” But I just wondered if, given that you were a UVA student and are UVA alum, someone would come to you to say he wants to go to UVA instead of Charlottesville.

I apologize. I need to go back and look at that. I’m sure I had to give them some UVA color.

The different event I remember is the first time I ever saw him at the Pavilion during his first campaign. This was when I hadn’t graduated yet, and I saw him speak in person for the first time. Then later on during that campaign, Michelle Obama was coming here, and her team asked me, “Where should we go to eat?” I gave them a list of all the best restaurants around here, and then I said, “But if you really want a sense of what we did in college, go to the Virginian.”

So she went to the Virginian, and they sat in the back and ordered the chicken. I heard the owner of the Virginian was a very hardcore Republican and was not that happy about it. [laughter] You won’t see any pictures of this in the Virginian. But I heard that, and I thought, Wait, you went to the one at the bottom of the list? I gave you a lot of good places to go. But they went to the Virginian. I’m sorry. I’ll have to go refresh my memory on that.

I’ll definitely check on the date, but I’m pretty sure.

Yes, I’m sure you’re right.

Then she was supposed to come, that date I don’t remember, but I was going to go see her come speak here, and then the Aurora shooting happened. She didn’t think it was appropriate to be speaking in public, so she had to cancel that.

Obama came with [Emmanuel] Macron, right, to Monticello?

We were doing an oral history that day, and we talked about Macron coming to Monticello, but that I don’t recall. If you remember that the President came, I’m sure he did.

Man, I’ve got to go back and check this out. I’m sorry.

You’re permitted to write up in the appendices the things you want.

I’ll double-check my date on that.

OK. I’ll go back and look through.

If certain things occur to you, just quickly type up some additional thoughts. You can put it at the end, and it works just as well as the interview.

So, Favreau leaves in ’13 and Cody Keenan, as you’ve said, becomes your boss. Then you move up again: you become a special assistant to the President and deputy director of speechwriting. How does your job change at that point? Is anything happening in the structure of the speechwriters office?

As a more senior speechwriter, I would do bigger speeches. I would edit the speechwriters more often. It didn’t change that much, but I was doing slightly different things.

Did you find it hard to supervise other speechwriters?

Not really. We were such a small team that everybody felt pretty comfortable with each other. We wouldn’t edit each other that much, but we would ask each other for feedback enough that it wasn’t like I was giving people feedback for the first time.

As we started our conversation today, this was your dream job. Given that, how did you decide to leave it then in July of ’14?

Looking back, I wish I had stayed a little bit longer, but at the time I remember feeling like Cody was going to stay for the rest of the administration. I was not going to be the director of speechwriting. The pace was pretty relentless, as we talked about. I also wanted to try California. I had grown up around D.C., lived there my whole professional life at that point. I felt like I was writing similar versions of speeches and was a little burned out.

So, yes, my then-girlfriend, now wife, and I decided to give California a try. Looking back, I feel like I got off the ride a little before I should have. But at the time, it seemed clear. I think I must have been tired of it. I don’t know. It made sense.

And now you’re back on the ride in a different way, we understand.

Back on the ride, yes. I took a seven-and-a-half-year break, [laughter] which is probably good. Yes, ready to get back on.

That’s the last point I have to raise. Can you tell us about how you came back to now be a speechwriter for the postpresidency of Barack Obama? What is that like?

In between, I worked for Nest. I was Mark Zuckerberg’s speechwriter for Facebook, which is a whole different oral history.

If he’ll fund it, we’ll do it. [laughter]

Then I worked for Jim Ryan here [at UVA] and then went out on my own.

Is that right?

Yes, I was Jim’s speechwriter for the first two years of his presidency. I was looking for a way to come back to Charlottesville and actually knew him through Bill [Antholis], who offered to introduce us.

How did you know Bill?

He was not the director when you were at the Miller Center, right?

No. I think he might have reached out when I was still out in California. We had met there. He was there to talk to some other people. Bill’s a good finder and networker of people.

I was on my own, doing work for different clients. One of my friends, who was Michelle Obama’s speechwriter, was doing both Michelle and Barack Obama stuff after Cody left and said, “I just can’t do it all. Can you take the Barack Obama stuff?” So I did. The cool thing these days is because I’m the only one working with him, I get to work a lot more closely with him on a lot more speeches. And the pressure’s off a little bit. We don’t do as much. They’re not as important, but they’re more fun.

We did all the midterm stuff this past time. We did a big speech on social media and things like that. I think we’re going to do another one on inclusive capitalism. These are interesting things that he’s thought a lot about. It can be a little crazy because now I have two young kids. He’ll call to talk through edits, and one time he heard both of them having a meltdown in the background at the same time. And he was like, “Should I call back later?” [laughter]

He’s been there.

Yes, he’s been there.

[END OF INTERVIEW]