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SAM SANDERS, HOST:
Hey, y'all. Sam Sanders here. IT'S BEEN A MINUTE. Every Tuesday on the show, we bring you a deep dive. Today, we have one of the youngest speechwriters in the Obama administration, probably in any White House. His name is David Litt. David was writing speeches for President Barack Obama at the age of 24. I know. What have we done with our lives? Anyway, he has a new book all about the experience. It's called "Thanks Obama: My Hopey, Changey White House Years."
Bit of background - David left the White House in 2016 before the election, and now he's a comedy writer for the website Funny or Die. During his time in the White House, David wrote a bunch of the president's funny speeches - White House correspondents' dinners, that kind of thing. And there's a bunch of good stories in this chat about all of that. But there's also some real talk, too. David is really honest about how he and so many others kind of fell in love really hard for candidate Obama. And then at some point came to realize Obama, just like them, was a mere mortal. Anyway, that should get you started.
Here's me talking to David Litt here in D.C. His new book is called "Thanks, Obama: My Hopey, Changey White House Years."
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SANDERS: Where are you from?
DAVID LITT: I'm from New York City, grew up on the Upper West Side.
LITT: You're a Texan, right?
SANDERS: Google. Yeah, it's true.
LITT: Yeah, I Googled.
SANDERS: Yeah, OK. OK.
So walk me through how you get from - what? - Upper West Side or Upper East Side?
LITT: Upper West Side, please, we're the down...
SANDERS: What was that please about?
LITT: Well, you know, I feel like we're very proud on the Upper West Side of being the, like, down-to-earth totally...
SANDERS: That's right. Salt of the earth.
LITT: ...Sheltered kids. Right. Like, we're the second-most sheltered children on the Eastern seaboard.
SANDERS: Yeah. So you open your book by describing the scene of falling in love with Obama while taking a plane back to New York from somewhere. Walk me through that moment when you saw Obama giving this speech and you're, like oh, that's it.
LITT: So I was flying...
SANDERS: And how old were you?
LITT: I was 21. I was a senior in college. And I had just - I spent the summer before interning for The Onion. And...
SANDERS: I know those people.
LITT: Love The Onion.
LITT: Discovered I was not great at writing Onion headlines.
SANDERS: Well, it's hard.
LITT: And they get so many. And I sort of had that moment - and I say this in the book - there's kind of like - it can be hard to tell the difference between the absence of talent and the presence of destiny where I was like, OK, maybe I'm - I should do something bigger, by which I meant I'm not going to get hired at The Onion. And so I went - you know, I wanted to join the CIA. That didn't work because I had smoked pot two months before my interview, so they cut that short. There's some rule that they had.
SANDERS: Some rule (laughter).
LITT: Yeah, so I don't know. And with that done - and I was trying to kind of figure it out. And I was on a plane. It was the end of winter break. We were going into JFK Airport. And it was - you know, they still had free cable on THE flights.
SANDERS: Was it JetBlue?
LITT: It was like - it was JetBlue.
SANDERS: Yeah, I think they still do the cable stuff.
LITT: They still do. And I - yeah, I'm deeply appreciative. And I was just kind of scrolling around. And I knew about Barack Obama. I had seen his speech in 2004.
SANDERS: At the convention.
LITT: Yeah, all of my friends who were really idealistic and earnest were into his campaign, but I...
SANDERS: So you weren't idealistic and earnest.
LITT: No, I think I wasn't totally apolitical. It's not like I didn't know that there was an election going on. The - I had volunteered on John Kerry's campaign. And I think he would have made a good president.
SANDERS: Well, that'll disillusion you.
LITT: Yeah, but it left me feeling, like, you know what? The idea that I could have done something and the idea that all of my knocking on doors and believing was making a difference was pretty dumb. And then I saw Barack Obama speak.
SANDERS: What was his speech?
LITT: It was after the Iowa caucuses.
SANDERS: So he had won Iowa.
LITT: He just won.
LITT: And I tuned in 30 or 40 seconds before he started. And he - I mean, from that first line, you know, he said - they said this day will never come. And I just remember having this moment that was like, oh, this is how presidents sound. You know, I never heard a presidential candidate in my lifetime sound so in command in that way.
SANDERS: But did you also - if I recall correctly reading this, did you also kind of like nitpicky edit that line too?
LITT: No, it's one I think about now.
SANDERS: Who is the they? (Laughter).
LITT: Yeah, it's...
SANDERS: Never? You want to use absolutes?
LITT: This is what I wanted to talk about in the book, right?
LITT: Is that looking back on it now, I recognize that there are some parts of that line where, you know, the idealistic part of me still watches that speech and kind of tears up a little bit and the more practical speechwriter part kind of looks back and says, well, actually, technically, if you look at it, you know, if Edwards wasn't in the race, probably Hillary would have won. And, you know, at the time she was leading...
SANDERS: There's an explanation for this.
LITT: Exactly. And so, you know, it's not actually that surprising when you think about it, particularly given the war and all the other stuff going on and so on. And how to juggle both of those parts of me because that's what happens, I think, when you move to Washington, but it also just happens as you go from being a college kid to being somebody who's a little bit older than that. You kind of have to have that moment where you figure out, how do I...
SANDERS: How do I do both?
LITT: Yeah, how do I do both? How do I stay an idealist and a realist at the same time?
SANDERS: How did you?
LITT: Probably by a lot of gallows humor. I think for me that's where - because I think that's the other challenge. You move to Washington, you get a dream job, you start to feel like maybe I'm really indispensable to the president. You forget you're just, like, a junior-level speechwriter. And so I think to some extent, by trying to stay focused on what's funny about this or, you know, tell the story about the time I embarrassed myself in front of the president...
SANDERS: There were a few.
LITT: Oh, there were a few.
SANDERS: You were...
SANDERS: You did not hold back.
LITT: Yeah, I mean, well, even at the - I think it's in the last chapter or the second-to-last chapter where I talk about being on Air Force One and realizing that I'm not going to be able to change clothes in time before we land in Germany. And I'm like, this is bad. Am I going to, like, walk out onto the tarmac? I'm wearing these Hulk pajama pants. You know, is Angela Merkel going to be there? You start to have this catastrophic thinking. And when you're in the White House, catastrophic thinking takes on this sort of international...
SANDERS: We should back up.
LITT: Yeah, please. All right.
SANDERS: 'Cause I read it, so I know.
LITT: Yeah, yeah.
SANDERS: But, like - so you were on an overnight trip on Air Force One. And that means that overnight everyone sleeps and, like, wears pajamas.
SANDERS: You were late to get in line for the bathrooms to change out of your pajamas.
LITT: Yes, this is the...
SANDERS: You had also not slept.
LITT: I hadn't slept. I had never been on an overnight flight before, so I was - I did not know that it was going to be different than just a, you know, flight to Kansas City or Los Angeles or something like that. And I didn't take a sleeping pill.
SANDERS: Which they pass out like candy.
LITT: Which they passed out because I thought what if it's, like, 5 a.m.? And, you know, I'd written this speech about how fun it is to be in Germany and joke about lederhosen. This was not a, like, important speech.
SANDERS: Had you been to Germany before?
LITT: I had - I think I had been, like, once with my parents when I was 10. But this is not practical research. This was a sort of, you know, lederhosen, beer, pretzel speech before the president...
SANDERS: All of those things sound fun.
LITT: Oh, yeah. I got to write the fun stuff. And then other people had written the sort of serious we need to - you know, here's what we need to do about the Eurozone or whatever. But what if the president had edits to that speech early in the morning? I didn't want to be not able to focus. So I hadn't slept all night. We get up and they give us breakfast. And I ate the entire thing - should not have done that. And by the time I'm done eating and I look up from my enormous tray of food - because the food on Air Force One, they always gave you too much food. So I looked around. There's a room that has the computers and stuff - no doors in there. And I had this kind of stroke of insight where I realized there's a coat closet. My suit's in there. All I have to do is sneak into the coat closet, close the door...
SANDERS: And I can change.
LITT: Yeah, change my clothes. And I almost pulled it off. But almost is a very important word in this scenario.
SANDERS: Yeah, almost doesn't count.
LITT: It really does not count in - yeah, only in horseshoes and hand grenades and definitely not when changing your clothes on Air Force One 'cause our trip director opened the door - and, of course, the coat closet opens directly into the staff cabin. So everyone just sitting there suddenly sees me with...
SANDERS: In your underwear.
LITT: Me in my underwear staring out at the rest of the presidential staff on Air Force One. And I think - I heard that this story was so popular among staff that on later flights people would re-enact it, like, just to see whether it would work. So I think that as I look back on some of these stories I feel like that intense urge to get it right when it's so intense that it makes you do it wrong...
LITT: ...I feel like I did a lot of that.
SANDERS: That's just such a...
LITT: That's probably something a lot of my colleagues didn't do because they were a little bit better at figuring out the balance than I was.
SANDERS: It's also, like, a testament to youth. I feel like the guy that I was seven or eight years ago would do things wrong to get it right. And I feel like the older I get, the more I'm better at just saying, the line's too long for the bathroom. I can't change. Hey, boss, let me just change once we get to the venue. Is that cool?
LITT: Yeah, kind of getting used to the idea that, like, I am pretty imperfect, and that's going to be OK.
SANDERS: Yes. And I can admit that.
LITT: Right. And I'm also not quite as smart as I think. Like, that brilliant coat closet idea, there might be a downside that I don't see.
LITT: But I'm just going to trust that maybe I shouldn't do that.
LITT: Yeah, I learned that lesson.
SANDERS: That's a good lesson to learn. Let's walk through how you got from seeing Obama on that plane to working for him. You didn't - it took you a few steps. You interned a bit elsewhere before you got in there. Take us through that.
LITT: So I landed, became one of those people that would not shut up about Barack Obama. Then I graduated in 2008, May of 2008, and two weeks later got in my car, drove to Ohio and worked as a field organizer in Ohio on the campaign. So basically where as a volunteer, I had been knocking on doors and telling people to go vote, now I was calling up supporters and getting them to knock on doors and tell people to go vote. And it was a great experience. And in many ways, it sort of felt like exactly what you always want out of politics. I mean, it was this moment when for all the craziness of a campaign and all the late nights and all that stuff, it just felt like things gradually - this entire community is realizing how powerful it can be and how together we can change this country.
SANDERS: So you finish your work with Obama.
SANDERS: He wins.
LITT: He wins.
SANDERS: But you're, like, waiting around to get an administration...
LITT: Yeah, so...
SANDERS: ...Job possibly.
LITT: Exactly, so then I move back home with my parents.
LITT: And then I decided that was not going to work.
SANDERS: Upper West Side not going to work for you anymore.
LITT: (Laughter) It was less the Upper West Side and more the - like, the feeling of sitting on your...
LITT: ...Childhood bed, like, staring up at your most-improved certificates from summer camp and wondering what on earth you're going to do. So I move to D.C., and I didn't really have a plan other than like hope and change.
SANDERS: That's a great plan.
LITT: But I just knew Obama's in Washington. I want to be there.
SANDERS: Yeah, well, you wrote - and I love this line - you...
LITT: Was it the Phish thing?
SANDERS: Can you quote it?
LITT: Yeah, I was - well, what I said was, I didn't move to D.C. to get a job with Obama - or hoping to get a job with Obama any more than a Phish fan goes to a Phish concert hoping to get a job with Phish.
SANDERS: Although if those Phish dudes were offered a job with Phish they'd be like, oh, my God, yes (laughter).
LITT: Yeah, which is exactly how I was when I was offered a job with Obama, right?
SANDERS: Yeah. yeah.
LITT: And so I didn't really think that I was going to get hired by the administration...
SANDERS: And you had different gigs before...
SANDERS: ...Because you were at - what? - like, a firm you could not name.
LITT: Yeah, I was at a crisis communications firm. I think I was the worst intern in Washington, D.C.
SANDERS: This is the one where you played Minesweeper all day?
LITT: I played - yeah, I mean, I would only answer work-related questions in analogies to the game of Minesweeper I was playing at the time.
SANDERS: (Laughter) Give me an example of this.
LITT: So - and I thought this was such a good, sneaky, brilliant, subversive thing to do. So somebody would be like, you know, have you - do you have that memo ready? And I would say, well, it's almost done. But you know how when in Minesweeper you've gotten, like, 97 of 100 mines, but you still have three left, but you have like five squares, so that's the really hard part, is the very end...
SANDERS: That's where I am right now.
LITT: ...Because you're trying to figure it out? Yeah, so that memo might not be done for a little bit.
LITT: And as if by, like, the fourth or fifth Minesweeper answer it was not incredibly obvious what I was doing or how terribly obnoxious I was.
SANDERS: Yeah, you kind of - you were kind of a turd.
LITT: Yeah, I was kind of the worst. And this is one thing I do talk a little bit about in the book, is that I sort of came from a universe - I went to Yale and, you know, knew people from, like, growing up in New York, going to high school and whatever - where I kind of got second chances I did not necessarily deserve.
LITT: And I think - and I felt like it was important when I was writing the book and even just talking about it - to say, like, most interns who do that don't get another shot. But I was lucky enough that I met a speechwriter named Dan Benaim, who at the time was writing for John Kerry in the Senate. And we had coffee and he said, we had this thing we wanted to write - I think it was a piece for root.com.
SANDERS: The Root?
LITT: Yeah, The Root, the Slate offshoot?
SANDERS: Yeah, yeah, yeah.
LITT: And he basically was like, one of our interns tried to do it, didn't go great. You want to give it a shot over the weekend? So I spent the weekend working on it. He thought it was good and said, you know what? You should intern with this speechwriting firm called West Wing Writers.
SANDERS: Did that guy make a call for you to get into West Wing?
LITT: Yeah, exactly.
LITT: So he knew the partners there. The thing about speechwriting, it's kind of hard to break into. But then once you're a speechwriter, there's so few of them that everyone...
SANDERS: Knows everybody.
LITT: ...Kind of knows each other or at least knows someone who knows someone.
SANDERS: OK, so you meet someone who knows someone.
SANDERS: Someone that you know who gets you this internship at West Wing.
SANDERS: And then you go from West Wing to...
LITT: Well, yeah, so all of their associates were leaving it to write in the administration.
SANDERS: Got you.
LITT: And so two weeks in, I was, like, the fifth-most senior - sixth-most senior person at a six-person firm.
LITT: But still, it was like the partners...
LITT: ...And the office manager and me. So they hired me to stay on. So I did that. And basically, I just got lucky because Valerie, who was the president's senior adviser...
SANDERS: Valerie Jarrett...
LITT: Valerie Jarrett.
SANDERS: ...Who loves to end her sentences in prepositions - not in prepositions.
LITT: No, she does not end her...
LITT: Yes. So I don't mind ending sentences in prepositions.
SANDERS: Well, because, like, humans.
LITT: Right. Well, and also, you know, I think it's just a style thing, right? And I say this in the book. It wasn't that I thought I was right and she was wrong.
SANDERS: It's just a difference of style.
LITT: Exactly. But if you're a speechwriter and your boss has a difference of style, they're right.
LITT: That's the rule, and...
SANDERS: Did Jarrett's people in the White House just call West Wing and say, who you got? Or was there another connection of connections?
LITT: You know, so my bosses at West Wing Writers had sent my writing samples to Jon Favreau, who was the chief speechwriter in the White House at the time. And I sat down with him, and he kind of said, you can do the application process. You can try to become a presidential speechwriter. Or we have this job opening for Valerie and for senior staff. You can basically be the only candidate for that job if you want. And I was like, OK, I'm going to go ahead and be the only candidate for that job.
SANDERS: And this is when you were 24?
LITT: That was when I was 24.
SANDERS: How did that feel? You were the only candidate for a speechwriting job in the White House two years after being the worst intern in the world.
LITT: (Laughter) Well, I would like to tell you it felt great. Mostly, it felt terrifying because I was sure it was going to fall through somehow.
LITT: Because you do the background check.
SANDERS: You spent a lot of time talking about trying to get through that.
LITT: Yeah, you know, you have to fill out every address you've ever lived at.
LITT: You know, like, some FBI agent called my mom and, like, talked to her for a while.
LITT: They'll check in with a friend and say, hey, by the way, you know - they're looking for inconsistencies, right? And then, you know, I did sort of have that moment - the first time I met Valerie and Mike Strautmanis, her chief of staff, and kind of had a quick interview with her and basically realized, like, barring some catastrophe, you have the job.
SANDERS: You got this job.
LITT: I mean, that was the moment you kind of - like, I walked back to my apartment and basically, like, immediately took my suit off because it was really uncomfortable and then just jumped up and down in my underwear and was like, this is amazing...
LITT: ...And, you know, yelled a lot of swear words at - just into the air.
LITT: And it was incredible, but it's also - that's the - the crazy thing about White House jobs is it's this mixture of this incredible experience and this thing you wouldn't give up for the world but also an incredible amount of responsibility and stress and having both of those at the same time. And it definitely gets to you in weird ways.
SANDERS: Yeah. All right. Time for a quick break. When we come back, meeting the president and what it was like to work on a staff of mostly white male speechwriters working for the first black president.
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SANDERS: All right. So two questions. How did you move to the Obama speechwriting staff, and what was it like to meet him for the first time?
LITT: So the basic - the way that most D.C. opportunities happen is people are too busy to do whatever they need to do. And so they give you what they don't want.
LITT: And the nice thing about when I was working for Valerie and for Bill Daley, the chief of staff and others was I would do my work for them but then kind of gradually - if there was something the presidential speechwriters didn't have time for or didn't want to deal with, I would also take that on. And so it became a sort of easy way to get to try to do some speeches for the president where - you know, most people don't want to do the Thanksgiving video after they've already written three Thanksgiving videos. Like, it's...
SANDERS: Yeah, we've moved on.
LITT: ...You've said enough about Thanksgiving.
LITT: But for me, it was like, this is amazing. This is my - this is the biggest day of my life. So I got to be that guy who's excited about the stuff no one else wants to do. And I think that was how I started to pinch-hit a little bit more for - on the president's team.
SANDERS: The Thanksgiving speech - this is where you forgot to say God.
LITT: Yeah, I...
SANDERS: Or was it another speech?
LITT: ...Left God out of that speech. I feel like you said that in a way where it's like, have you apologized to God? I'm like, well, no. Not yet.
SANDERS: It's OK. It's all right. She'll forgive you.
LITT: (Laughter) So this Thanksgiving Day speech - that was the first time I met the president.
LITT: And this was - we did the taping. So it was in the diplomatic room of the White House, one of the most beautiful rooms in the entire building. It feels very White House. And I was standing there, and the woman who filmed the president, Hope Hall, basically said, like, don't worry. I - just wait. It's going to be fine. And so we're waiting, and all these things always run late. We're waiting forever. Finally, the president walks in, and he's standing up. We all stand up. And he sits down. So we all sit down. And he's about to start filming, and Hope stops him and says, Mr. President, this is David. This is the first video he's ever written for you. And President Obama looks at me and says, oh, how's it going, David? And I...
SANDERS: How do you answer that question?
LITT: Well, I remember having exactly one thought, which was I did not realize we were going to have to answer questions. That's the only thing I remember thinking.
SANDERS: (Laughter) You're like, I already wrote this stuff, man.
LITT: Yeah, you're like, I have no - and, like, it's, like, how's it going? I was, like, what am I going to say? And then I don't know. I literally blacked out.
LITT: Like, the first time I met President Obama, I blacked out. And the first time I went into the Oval, I did not black out. Very proud of that.
SANDERS: Thank goodness.
LITT: Yes. But it was for this Betty White tribute video. and...
SANDERS: On her birthday.
LITT: On her birthday, her 90th birthday. And I - it was one of those moments where I wanted so badly for everything to go perfectly that I managed to make almost nothing go perfectly.
LITT: I opened my mouth to talk to the president and what came out was like I was trying to ask for directions but in Spanish.
LITT: Like, the nouns and verbs were there, but there was nothing connecting.
SANDERS: The conjugation was lacking.
LITT: It was - yeah. It was a mess.
LITT: And given that my job was also to write stuff, the fact that I, like, tongue-tied does not begin to describe it. I doubt I made a very good sort of second first impression.
SANDERS: But he must be used to that.
LITT: Yeah, I think he kind of gave Hope a look that was like, oh, another one, you know?
SANDERS: Yeah. Yeah.
LITT: Like, I have heard since from a number of people who blacked out when they first met Obama.
LITT: And so - and also people who were there - where, like, a celebrity would meet Obama. And they'd have - and, suddenly, that person who is normally the most famous person anyone's going to meet that year just, like, can't handle it.
SANDERS: Oh, yeah.
LITT: Yeah. So it was - and, actually, one of the really cool things, once I was at the White House for a while, was getting to be parts of those moments for other people. Like...
SANDERS: You'd see it happen to others.
LITT: Yeah, you'd see it happen during a speech. Or, like, he would meet someone who you interviewed because he's going to tell their story in the speech. And...
SANDERS: An RP.
LITT: An RP - a real person.
LITT: And so he's meeting an RP. And you realize, like, in some tiny way, I got to be part of the most memorable moment of this person's life - maybe except for the birth of their children, right? And that was really special. Like, just you realize how much that's going to mean. Every time the president walks into a room is like the biggest thing that happens to everyone else in that room constantly. And it was just - that was an amazing feeling.
SANDERS: I love how you bury the lead with the - like, with the whole Betty White story. You forgot to tell listeners that you ended up having to hum the theme song of "Golden Girls"...
LITT: I did not. I sang the theme song.
SANDERS: You sang the theme song...
SANDERS: ...To the president.
LITT: To the president. That was the only thing I did right...
LITT: ...Because at the end of it, he was supposed to put on headphones or put in ear buds, pretending to listen to the theme song from the "Golden Girls" - Betty White's most popular show. And he stops, and he says, well, shouldn't I bob my head in time to the music? Wouldn't that be funnier? It's just like this little thing where it's, like, oh, you're rescuing the economy, but also, yeah, that would be funnier. How did you do that?
SANDERS: But also sidebar - how did you, Barack Obama, not know the theme to the "Golden Girls" by heart? It's a classic.
LITT: I like - like, people have their criticisms of Barack Obama. And yours is...
SANDERS: (Laughter) This is my biggest critique (laughter).
LITT: Yours is, excuse, me, Mr. President...
SANDERS: Know the culture.
SANDERS: So he wants to know what it sounds like.
LITT: Yeah, and I - so he looked at Hope, the videographer, and she didn't say anything. So I looked at Hope, and she didn't say anything. So President Obama looked at me. And suddenly I was, like, OK. I know what I can do for my country.
SANDERS: And you did.
LITT: And I stepped up. And I was - yeah.
SANDERS: Thank you for being a friend.
LITT: (Singing) Thank you for being a friend.
And so that...
SANDERS: How long did you sing?
LITT: I think I got through, (singing) invited everyone you knew.
SANDERS: That's deep in there.
LITT: ...That was when he kind of gave me a look that was, like, OK. Because he seemed kind of amused.
LITT: So I kept going. And we were talking, like, kind of special moments. I have a friend who worked on Betty White's show on TV Land...
LITT: ...And said, like, that was a huge - you know, she got the card from the president and was, like, this is so special.
LITT: It's just like you get the chance to make someone's day, like, exponentially better in all these little ways. That mattered a lot, too. Not just the kind of big, national stuff.
SANDERS: Yeah. So you end up - you know, you work your way up from writing for Valerie Jarrett, to writing to, like, all senior staff, then writing for Obama. But you talk about in the book how, at certain points, Obama's speech writing team was, like, a bunch of white dudes, right? And you talk about some of the privileges that helped you get this job. What was it like being who you were and the team that looked the way it did writing for America's first black president?
LITT: Well, one thing I'll say about this speechwriting team - because I do talk about when I started at...
SANDERS: It changed over time.
LITT: Yeah, it changed over time.
SANDERS: But there was a moment when it was white guys.
LITT: Yeah. And speech writing, I think - unfortunately, like, now I'm in comedy writing. So I just kind of keep going from the industries that could use a little...
SANDERS: (Laughter) Let me tell you buddy, but I work in public radio. I know what you're talking about.
LITT: (Laughter) Yeah. So - but it's the same kind of thing, where it is - there's a challenge of just we should - especially progressives - should be getting more people from more different backgrounds just in the beginning of the pipeline. And I think it's good that the Obama administration did that. West Wing Writers is doing that. A lot of people are doing that now. But I don't think that there was ever a moment when - you know, for example, I wrote - when I wrote speeches for President Obama, I thought, well, am I capable of doing this? Because he had - you know, he's an African-American president, and I am a not African-American.
SANDERS: He didn't grow up on the Upper West Side.
SANDERS: Like, you guys are different.
LITT: Exactly. But I think partly because he was and is such a good writer - that when there were parts that he just needed to add from his own experience, he would do that.
LITT: And there was never a sense of, like, he needed you to translate his experience because...
SANDERS: He knows his experience.
LITT: He - exactly.
SANDERS: Were you ever afraid to touch on race or certain topics because of who you were - are?
LITT: I think there were moments where you tread carefully around those things...
SANDERS: Give me a moment.
LITT: You know, for example, I talk a little bit about - at the end of my time at the White House, I wrote a speech about criminal justice reform.
SANDERS: I remember this. It went over quite well from what I could tell from what you wrote about it.
LITT: Yeah, it was - I think the speech - the sort of non-joke speech that I'm proudest of...
LITT: ...That I worked on. And, obviously, that's an issue that has something to do with policy. But it also has to do with race and justice and equality. And, you know, the way I thought about it was I'd - like, I come from a background where if you were caught, you know, with a small amount of drugs or even selling a small amount of drugs, that's a mistake. And if you come from a different part of Manhattan, even, or look a little different, that's a crime, and your outcomes are totally different.
LITT: But I wasn't sure exactly how far to go in talking about that. And when the president made edits to that speech, it came back much sharper. I think he had just - you know, it was not surprising. He had done a lot more thinking both because of his own life but also throughout his career in politics about exactly what these disparities meant, what they looked like, why they were unfair, but also how to talk about that unfairness in a way that would translate not just to the crowd at the NAACP convention but also to a, you know, 50-year-old white guy watching from his couch somewhere.
SANDERS: Yeah. And that, I mean - that, to me, was, like, a tightrope you and the speechwriters and Obama were constantly walking. You had to talk in every speech to black America and to white America and to this, at sometimes, fragile coalition that emerged in 08' and 2012 to support Obama that a lot of folks thought could not hold together, you know? And you can see that work. And I wonder how much of that work and it working is informed by not just the black guy writing about race and his speeches but writing about it with white guys, too, you know?
LITT: Right. Well, you know, I don't know the answer to that. And I will say from my perspective, where I wasn't - so I worked for Jon Favreau, who was chief speechwriter and then for Cody Keenan, who was the chief speechwriter.
LITT: And I think they're - when those really thorny issues came up, they would work that out with the president.
SANDERS: Got you.
LITT: So I don't have a lot of insight into, like, this is the moment when we're in the room, thinking about these serious questions. A lot of the time, what I would do is kind of go back and say, what's the last speech the president has spoken about this issue in? How do I kind of take that but then update it for the current moment?
SANDERS: Got you. Got you.
LITT: But I do think one of the things that I am proud of - or that I was proud to see in the Obama White House was we definitely talked in speeches about how diversity makes organizations stronger. But as an administration, we also walked the walk. And over time, I think you could see the composition of the White House staff change to better reflect the people we were serving. And I do think that that made things much more effective.
LITT: I think it was good for everybody in the end.
SANDERS: Talk a bit about the nuts and bolts of Obama and his use of language. You know, we mentioned earlier that Valerie Jarrett didn't like to end sentences in prepositions. You wrote in the book that Obama was actually really, really good at long sentences.
SANDERS: What kind of things about the way he talks and writes became even clearer and more evident to you once you were writing for him.
LITT: Well, one of the very first things was the way that he not even writes but the way he thinks about an argument.
LITT: So there's an old speechwriting saying - tell them what you're going to tell them. Tell them. And then tell them what you told them.
LITT: And that's kind of that folksy style. If I was writing a Joe Biden speech, that's probably what I would've done.
LITT: Or, like, a Bill Clinton speech, even.
LITT: For President Obama, he sort of thought about it more like a lawyer making a case, right?
LITT: So you start with a beginning and a middle and an end. And also, I mean, he wrote, you know, his own memoir before he was in politics. So he's a storyteller.
SANDERS: Yeah. Yeah.
LITT: He wants a story that had, you know - it starts somewhere. It sort of comes to its logical kind of climax. And then it concludes. And that's different than a lot of speeches. And the other thing is some of it's kind of little, verbal tweaks. But more than that, like, I talk about long sentences. He had and has a gift for speaking that meant you could do more as a speechwriter. So a lot of the time, if you're writing for most people, I do think the best thing to do is write short sentences because people get lost in...
LITT: ...Long ones. And they don't know where to pause and where to stop and where to start and which word to emphasize. And so you just - you write even shorter than you would if we're just having a conversation. With President Obama, he could punctuate sentences even better than you would if you were doing it on the keyboard. And so if you gave him you know, a sentence that had six or seven clauses...
SANDERS: He could do it.
LITT: ...He could - he could not just do it. He could make it better than even, you know, the writer thought it was going to come out, right? He could kind of build to this crescendo that made you feel something, didn't just make an argument but kind of connected emotionally. And getting to do that was - that was really fun.
SANDERS: Sounds fun.
LITT: I mean, that's - yeah, it was. There's not going to be a better speechwriting job than the one that I had...
LITT: ...Because he's just - yeah?
SANDERS: Speechwriting now for the current president - that is another interesting challenge.
LITT: I'm sure it's an interesting challenge (laughter). I think - although, from what I've heard, they've - this may not come as a surprise - they've downsized the speechwriting office pretty considerably. Now, I think the thing that made me sort of have confidence in the speech writing process...
SANDERS: Yeah. Yeah.
LITT: ...Is that you can't obscure who somebody is with a good speechwriter.
SANDERS: Yeah, well what did you say? Like, speechwriters are like personal trainers.
LITT: Yeah, exactly. They're not puppet masters.
LITT: They're personal trainers, right? Like, you go to a personal trainer, and they will make you look like the best version of you. But they're not going to make you into somebody you're not.
SANDERS: They can't give you a new face.
LITT: Exactly. Maybe plastic surgeons would be the right analogy. But to me it was - you know, you look at President Obama's speeches. And, absolutely, he had a team of speechwriters. But they are a real reflection of who he is.
SANDERS: I also was interested by - you know, you wrote a lot of the comedy for the president. And he would do this thing where he would kind of punch up a joke that you guys had given him and make it even more funny - like, what was the one? When he wanted to put Biden in the NASCAR...
LITT: Oh, yes.
SANDERS: ...For the slide. Talk me through that.
LITT: Yes, so we...
SANDERS: Explain that.
LITT: It's a little bit of a complicated setup, but it's got a payoff, so it's all right. He had been skeet shooting in Camp David. And the White House put out a photo of him.
SANDERS: This was during the re-election? Or no, just...
LITT: It was right after. It was, I think, a couple of weeks after Newtown. And it was during the sort of fight over this background check bill.
LITT: And part of the point that the president was making is he's not anti-gun. He's going to go to Camp David, do some skeet shooting. And, of course, the right-wing...
SANDERS: Did he hit the...
LITT: I have no idea.
LITT: I was certainly never close enough to the president to be, like, you know, behind...
LITT: He's like, pull, and I'm like, all right.
LITT: That never happened. But - so anyway, we had this picture of him skeet shooting. The right-wing immediately decided somebody had doctored the image, that Barack Obama would never actually shoot a gun. You know, he's anti-gun. And so Cody Keenan, the chief speechwriter had this idea for a slide where we would do...
SANDERS: For the correspondents' dinner.
LITT: ...For the correspondents' dinner where we would do what really happened that day.
LITT: Like, it was doctored. We admit it. And then, in fact, the real version would be something that was, like, totally insane. So we had...
SANDERS: What things were in the shot?
LITT: We had, like, a giant kitten shooting lasers out of its eyes, and the president was riding. I think the first version was, like, a monster truck, you know, and he's, like, still shooting his gun. And, you know, there's, like, lightning bolts, and it's just, like, totally insane scene. And we showed it to the president, and the - his only edits were like, can we have a NASCAR?
LITT: ...Which was smart because it is, like...
SANDERS: It's very smart.
LITT: Yeah, it's, like, the little thing, right? Like, a NASCAR is better. And then we're like, yes, Mr. President, we can do that. And then right as we're about to leave, he's like, can Biden be driving the NASCAR? And you're like, yeah, that - Biden can be driving the NASCAR.
SANDERS: That's it. That's it. He gets it.
LITT: Right, and he - and I think that's - what I talk about is when people say that President Obama was the smartest guy in the room, I think a lot of what they were referring to was, he could just get the - figure out the essence of something really quickly - like, way faster than anyone else I've ever had the privilege of seeing do that. So he could figure out what was important and make the decision that needed to be made or do the thing that needed to be done based on that. Like, he had that ability to focus on the right thing. And I think when you look at the contrast between President Obama and President Trump, so much of it is, can you focus? And do you know what to focus on?
SANDERS: You underscore how much of a hand you had in the humor that is now quintessential Obama. You played a part in him doing the "Between Two Ferns" interview. You played a part in him doing the thanks-Obama BuzzFeed video. You actually were the catalyst for Luther the anger translator at the correspondents' dinner where - I get them confused - Michael Keegan Key?
LITT: Keegan-Michael Key.
SANDERS: Keegan-Michael Key was Obama's anger - like, that - you set that up because you saw him somewhere and were like, I like your jokes. Maybe one day, do a thing with the president. And then you made it happen. Like, how does it feel to know that, like, you were a part of some of what is now quintessential Barack Obama?
LITT: You know, it feels totally bizarre that I had that opportunity. Writing about the book, sometimes I felt like I was writing about someone else's life because it was so - you - so strange to find yourself doing that.
I mean, the thing with Keegan is a perfect example, right? Like, that wouldn't have happened if President Obama wasn't already a fan and we hadn't already talked about doing it. But then you have these moments where every so often - most of the time in the White House, unless you're a very important person, you're a cog in the machine. And I was proud of the machine I was a cog in, so I'm not - I think that's great.
SANDERS: You're also a very important person. It's OK, you are.
LITT: Thank you. I appreciate that. No, but in all seriousness, you're kind of doing your job and hoping not to screw up, and most of the time, you don't. But then every so often, you just kind of have a moment where you say, oh, hey, I met this guy at a party. I, like, followed him around the buffet table until I tracked him down, got his email. And now because of that, the wheels get set in motion, and, you know, a few weeks later...
SANDERS: It's a thing.
LITT: It's a thing. And 35 million people watch it in - on Facebook in the first 24 hours, which is crazy. It certainly makes me feel proud. But it also - that experience gives you a sense of just how rare and lucky this is. I think one of the things that I came away from my time at the White House with was an even stronger appreciation for just how lucky you have to get for those dream jobs or moments in your dream job - for those to come together.
SANDERS: Yeah. You know, you talk now about how skilled your boss was at a lot of things, but there's a portion of the book where you talk about the moment you kind of fell out of love with him. And you say that you began to see Obama as just a guy, right? When did that happen? And how did that feel?
LITT: Yeah, so what I talk about was the first debate in 2012 and...
SANDERS: Against Mitt Romney.
LITT: Against Mitt Romney - and from the very beginning of that debate, it was clear that things were not going well. And we didn't even need things to go that great because we were up, like, seven - six, seven points in the polls.
SANDERS: Romney had just had the 47 percent comment.
LITT: Right - just had the 47 percent comment. You look back at that now, and you're like, that's a comment that was going to sink a candidate? But at the time, that was true. And so all we needed was, like, a tie or even a slight loss, and we were done. Like, the re-elect was over. We were going to win.
And the president, I mean, he just - he looked like he didn't want to be there. And I remember watching and just - it - what he said - if you read the transcript of the debate and that's the only thing you were judging from, he actually did pretty well, in terms of the arguments he made.
SANDERS: But as you wrote, these are, like, not real debates, they're dog shows for people.
LITT: Exactly, yeah. It's theater. And he just didn't - he was just - did not want to do the theater. At least that's what it looked like. And that's certainly the way that Americans felt about it when they were watching. And it was this moment where, to me, I mean, what - if in 2008, I kind of had that pure feeling of love - right? - that just like, I'm an Obama bot. Whatever this guy - he - this is the perfect guy.
SANDERS: Pure feeling of love.
LITT: Yeah, I mean it was like just having an enormous crush immediately - just politically rather than physically. And that's the thing that I think went away that night. It's not that I didn't - you know, I continue to think Barack Obama was a great president. I'm proud of what I did and proud of what we did.
But this idea that somebody can be just even better than human - right? - fundamentally, that was just a moment when I had to reconcile myself to the fact that even incredibly impressive people are people. And they don't always do exactly what you hope they will do when the stakes are high.
SANDERS: Were you crestfallen? I mean, how did you feel? Were you just like, oh, my God, this is the worst? Was it, like, a breakup or what?
LITT: It was - the couple days after were really awful. Like, everyone - I was working in the DNC headquarters at the time.
SANDERS: ...Because you had gone to help - right? - for the re-elect.
LITT: Yeah, I had gone to help on the campaign side rather than the official government side. And I mean, we all kind of trudged in. And it was so bad because you just didn't know how far, how bad things were going to get. Like, we just kept dropping in the polls every day. And I was just obsessively clicking FiveThirtyEight, trying to see what was going to happen. It was just this feeling of, did we blow it? You know, did - like, this was the biggest night of the campaign so far, and you want him to come through, and he didn't come through.
And to me, that's one of the things I did want to talk about in the book - was coming to this realization that you can admire someone and believe in them but without thinking that they're perfect because none of us is perfect. And I think in politics, too often, we're kind of looking for the perfect person to come and say, if - you know, if that...
SANDERS: If they come...
LITT: They'll save us, right?
SANDERS: But I mean, didn't '08 Obama kind of low-key do that?
LITT: Yeah, well, didn't he save us or didn't we feel that way?
SANDERS: Or didn't he kind of say sometimes? Well, there was the one speech where he's like, the waters will recede, and the this will that, and the that will this. Like, was - hearing what you're saying right now, do you think that, had candidate Obama and President Obama done a little better job of tempering expectations earlier on, there wouldn't have been such a blow for you when it happened for you and for others when it happened for them?
LITT: I mean, I remember very clearly, as a candidate, Barack Obama saying in a speech, I'm not a perfect man, and I will not be a perfect president. And I remember thinking, well, that's exactly what a perfect president would say, right?
LITT: And so I think there was not a - it was - would've been very, very hard to come up with enough tempering to keep the enthusiasm, which was so vital to the 2008 campaign, and simultaneously be realistic. Campaigns don't tend to be super realistic, and that's part of what makes them so exciting. They are about ideals. And I think that the next inspiring president we have, we will have this moment where we feel like, this is a chance to somehow be perfect.
SANDERS: You say next inspiring as if this one doesn't inspire you.
LITT: I'm not super inspired these days. I have to say. But I do think that we're then going to have to figure out, how do you exit the campaign mode and get into the more prosaic governing mode? And we're going to have to be realistic and recognize that it's not always going to feel like that.
And the only other thing I would say, because you sort of talked about falling in love, falling out of love with Obama - and the distinction that I would make - and I think I made this in a late edit - is that I feel like what really happened was my idea of what it meant to love a person, or a candidate or a country changed, that when I was 21, if I - like, I fell in love with, like, you know, about six different women per semester - basically, only unrequited, but still - and you know, and certainly, like, fell in love with a candidate - and what I meant was kind of, this person is perfect, and somehow they will fix all the flaws in me.
And over time, both in my kind of relationship with Barack Obama or the idea of Barack Obama, but also in my relationship with Jacqui, my fiance, or with how I think about America, realizing that love is not - that love is understanding that somebody has flaws and loving them anyway, and believing in them even when you're also disillusioned with them. I'm - this is - like, I don't want to speak for Jacqui but I do think...
SANDERS: Speak for Jacqui.
LITT: Like, she knows more about what's wrong with me than anybody. And she also loves me more than anybody, right? And that to me is a - that's a kind of secure feeling that is missing from the kind of love I so regularly fell in when I was 21 years old. It's not necessarily moment to moment. It doesn't have that, like, endorphin rush every single second. But there is something that feels right about it. And that's how I think about - when I think about Obama, you know, and his legacy, or when I think about what it means to love America, I absolutely feel that sense of love. But it's more of a grown-up kind of love and less of this kind of puppy love, you know?
SANDERS: It's a maybe we're just going to go to the movies Friday night this week...
LITT: Yeah, exactly.
SANDERS: And one of us might not like the movie. But what else are we going to do?
LITT: Right. It's a, you know, we're-going-to-stay-in-and-that's-fine kind of love.
SANDERS: Yeah, you could wear sweats.
LITT: Right, exactly, it's a sweatpants love for America.
SANDERS: (Laughter) Yeah
LITT: That's - yeah, but - and that's ultimately, to me, the - a lot of the book was about...
SANDERS: ...Getting to that place.
LITT: ...Kind of growing up in that way.
SANDERS: On behalf of all "Golden Girls" lovers, thank you for your service. It was a great conversation.
LITT: Yeah, this was really fun.
SANDERS: I really appreciate it.
LITT: Thank you so much.
SANDERS: All right, man.
(SOUNDBITE OF FLEVANS'S "FLICKER")
SANDERS: David Litt, so fun. Thank you, David, for coming in. The book, again, is called "Thanks, Obama: My Hopey, Changey White House Years."
And quick favor to ask - you know I always ask it. If you like the show, and I hope you do, leave us a review on Apple Podcasts, OK? Also, don't forget to share a recording of the best thing that happened to you all week for our Friday wrap. Send that audio clip of your voice to email@example.com. All right, that's a wrap until Friday. I'm Sam Sanders. Talk soon.
(SOUNDBITE OF FLEVANS'S "FLICKER")
SANDERS: I was not writing speeches for presidents when I was 24. I was traipsing through Boston drunk.
LITT: Well, I was traipsing through Washington drunk, it was just what...
LITT: It was the daytime. It was maybe different.
(SOUNDBITE OF FLEVANS'S "FLICKER")
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