Cody Keenan, Obama’s former speechwriter talks about battling imposter syndrome

And now from the University of Chicago Institute of Politics and CNN Audio, The Axe Files with your host, David Axelrod.

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If you’re a regular listener, you may recall my conversation a few years back with an old friend and colleague of mine, Cody Keenan, the former chief speechwriter for President Obama. Well, now Cody has written a book, a splendid book called “Grace: President Obama and Ten Days in the Battle for America.” It’s about ten eventful days in 2015, during which a lot of history was made, some soaring and some tragic. The book’s a wonderful window into Obama, his White House, and the role of speechwriter, really speech collaborator, to a president for whom the power of words meant so much. I sat down with Cody this week before an audience at the Institute of Politics to talk about this and his own journey. Here’s that conversation. Cody Keenan, it’s great to see you, brother. It’s been been a while.

Yeah, amen.

And I appreciate you being here. You’re you’re coming down from some school on the north side there.

I just start by saying thanks for letting Northwestern get in here. I just came from class.

Where you’re, where you teach speech writing. But it’s good of you to be here at the Institute of Politics, and we’re happy to have you. Chicago is is is really your original home. This is where you were born. You know, much of your youth was spent here. In fact, you were born in Wrigleyville.

That’s right.

And you remain to this day, I know, a loyal Cubs fan, Bears fan. And I was wondering if this is how you learned how to write so poignantly about sorrow and loss?

Yeah. The Venn diagram between being a Democrat and being a Cubs and Bears fan is a circle.

And your folks were in the advertising business. Creatives in the advertising, tell me about them. What did they do?

Well, they so they were in client relations, which really is a fancy way of saying they took clients to Cubs games, but they taught me how to tell a story. You know, it’s just they were they were selling, you know, it was the eighties, so they were selling cars and beer. But there’s a story to be told in every commercial. And I was just, there’s a there’s a marketing component to politics that I picked up from them.

Were you a writer as a kid? Was writing a big thing in your life? Is that something that you inherited from your your folks?

Yeah. My mother was also an English teacher in high school. Before she got in advertising, she got her masters in journalism from Northwestern. I was a bigger reader. I was a voracious reader, which I think is a direct parallel into good writing. I think to be a good writer, you have to be a good reader. And I, I’m doing a stop later on this tour in Ridgefield, Connecticut, which where I ended up going to high school and public school there. And my conversion will be my 11th grade English teacher, because she sent me on this course.

Watch your grammar?

Yeah.

Yeah. What did. And was politics something that you talked about in your house a lot? Was that something of interest to your folks?

My parents bickered about it a lot at the dining table. My mom had always been a liberal. She’d volunteered on the McGovern campaign, and she volunteered on the Ted Kennedy campaign in 80. My dad was a Reagan Republican, came from California, and they just kind of bickered over politics all the time. Not not real fights, not like today. Right. Where if you have a MAGA person and Democrat in one family, they might end up divorced. But it was just, that’s how I absorbed it. And I wanted to know what they were arguing about. And we subscribed to the paper edition of the Tribune, you know, and I’d plow through it to see what was going on.

When it was a real paper.

When you wrote there. Yeah.

Well, that’s what I meant. So you went off to Connecticut. Presumably they got jobs in the East and you were the quarterback of your football team and you got injured, blew out your knee.

Blew out knee, everything in it. I was out for two years and so I thought I wanted to be an orthopedic surgeon.

And then you came to Northwestern? Yeah. And like a lot of aspiring doctors, you then confronted chemistry and became a poli sci major.

That’s why they make you take chemistry first. No, I wanted- I loved biology. Give me that. But no chemistry and I did not get along.

Was there a focus of your studies in poli sci? Was it on American politics?

It was on American politics. And as a writer, I think the only poli sci course that I just had a real aversion to was statistics and polling and political research just didn’t make sense to me. Numbers. That’s why I’m a writer. I just couldn’t I couldn’t crack that.

And then you graduated and faced the terror of trying to figure out what to do. And some friends inveigled you to come to Washington.

Yeah, a couple of Northwestern guys pressured me into it, and I ended up living with one of them when I got there. And he was in Teach for America, which is incredibly important, but it was not useful to me to get a job in Washington. I knew nobody. You know, my parents weren’t donors, which is the way a lot of kids get jobs. I didn’t know anyone, so I just kind of. Back then, we used this website called HillZoo. I mean, this was before social media and before LinkedIn. And so there’s this janky website called hillzoo.com, where people would post internships.

HillZoo sounds like a barbershop.

Yeah, it was- it kind of used comic sans, you know, it wasn’t it wasn’t a great website, but I found my internship with Ted Kennedy there.

And what was it just that that was an internship that was available? Or did you, as a good Irishman, have an affinity for Kennedy, or what was it that attracted you to him?

Well, who I didn’t have a great I had a great political science degree and background and could do it right, almost anything. I didn’t have a great knowledge of how to get a job in politics, but I saw this ad for Ted Kennedy. And it’s not just that I knew who he was, and that I aligned with him on all the issues. But as a as a young Democrat, the chance to work for the last Kennedy brother was something that I couldn’t pass up.

You’re too young, actually, to have remembered the other. You were born after the other Kennedy brothers were. But you had a sense of him and the whole Kennedy mystique.

There was a sense of purpose to it that I wanted in my own life, a sense of public service and the idea that we can do something to make this country better.

Yeah. Why? I mean, why were you imbued with that? I know you said your folks argued about politics. But what gave you that sense of mission about public service?

Well, when I was thinking about becoming a doctor and then and then switched to politics, I realized why help just one person at a time when I can go help millions? It was- my dad is everything to me. But it was my mom’s kind of big heartedness, you know, always chiding me, well they both did, to to stand up to bullies, to always be nice to everyone in school, to to help other people out. And that just as you grow up, you try to think of other ways to do that. And I because I grew up and, you know, we ultimately moved from Wilmette to or from Wrigleyville to Wilmette. And it was just a place with, you know, amazing public schools, public parks, an incredible public library. And you start to think as you get older and realize what other people have and don’t, that I wanted other people to have the same kind of chance that this country gave me, that living here gave me. And the people I saw doing that were Democrats.

Yes. You started in the mailroom, which normally, you know, that’s like the sort of American story. You start in the mailroom, then you work your way up. But it turns out that working in the mailroom for someone who wants to be a speechwriter or wants to write about, you know, write in service of politics and public service is a pretty meaningful place to be. Talk about the letters that you would read when, and presumably Ted Kennedy got letters from all over the country because he was more than just a Massachusetts senator. He was an iconic figure when it came to the fight for health care and so many other things, equal education and so on.

Yeah, a lot of the letters flat out said, “My senators don’t represent me, so I’m writing to you.” But there are also a lot of people who would just wanted to write to the last Kennedy brother to touch that family in some way. But reading letters in the mailroom changed the way I thought about politics right off the bat. And I you know, my my idea of what it looked like came from the TV show The West Wing, because I was popular when I was in college and graduated. It was still on the air. And you get there and you read these letters and you realize quickly it’s just very, very different. And these letters would be, you know, people would splash their private hopes and pains on the page. They wouldn’t even necessarily be asking for anything in particular. There’s, any time a letter would come in and say, I’m having a problem with my Social Security benefits or whatever, someone in the Boston office would figure that out right away. But a lot of the ones that came to him in D.C. were they just wanted him to know what their life was like. And there was this kind of deep hope to it, even if they were sad that somebody on the other end would care, would read this letter and care. And that changed the way I thought about politics forever. And that changed the way that that I wrote forever.

Yeah. What did you do with the letters? You responded to each one of them, or did you pass them along to someone else?

We had the legislative correspondent who would do it all. I was- basically just my job to read and route them first. Ultimately, I graduated up to replying to them. But but it’s always, he was really good at constituent services.

Yeah. Famously.

Famously so, I mean, he had a whole office in Boston that just, if you had a problem, we’re going to solve it in an hour.

Yeah. You know, it’s interesting to me about that story, about you in the mailroom is my experience with President Obama. And one of the first things that he did was insist that he get ten letters a day. You know this because he would share those letters with us, ten letters a day from people across the country. People in the in the correspondence department of the White House would try and pick ten that were representative of the kinds of letters they were getting on on a particular day. And he would often respond to them, sometimes call them and we’ll talk a little bit later. I mean, there were, we could talk about it now. There were people, Natoma Canfield was an example of a woman who really was struggling in the health care system and was and she became a symbol for people within the White House and ultimately in speeches of why he was making that fight.

Mm hmm. He still has her letter on his personal office wall right now, framed. And the great thing about these letters was, you know, we would have morning message meetings where we talk about what goes into his speech. We would have access to polling data, focus groups. But I often found the most profound things came from those letters. I would change the way I thought about an issue based on the way somebody described it in those letters. And what makes that important for speechwriting is, you know, Bill Clinton was always famous for saying, I feel your pain. Right. But you can also show that you understand an audience what they’re going through rather than just have the president up there saying, I understand student loans, which he did, because he had just finished paying them off about four years where he ran for president.

Yeah. He’s doing better now.

Yeah. But you could tell somebody’s story in a speech, and we often would, and you’d see the audience nodding along. And they would. They would say, you know what? I understand that person. I am that person. That’s my life story. And it was really profound. And there was this one in particular, Rebecca Earler, who wrote this long, beautiful letter coming from Minneapolis in 2014. And she just wanted the president to know what her life had been like through the recession and beyond. Didn’t, again, didn’t ask for anything. There were a couple of things that can make life better for someone like me, she’d write, but it was such a beautiful letter that we reached out to her and asked her to introduce the president at an event in Minneapolis. And she did. And I stayed in touch. And then when it was coming, time for the 2015 State of the Union address, rather than, do, you know, go through all the people in the first lady’s box. We built the speech just around this woman, Rebecca. The economic portion was all custom tailored to her life and her letter. And I’ve, I texted with her this weekend. I mean, we’ve become friends because she’s just, she and her husband are my age and they’re just cool.

And they bought the book?

I hope so. But they’re wonderful.

You know, the other reason why it’s so important and I still you know, we’ll talk more about the interweaving of stories and storytelling as part of speechwriting. But the White House is such an isolating place. Our friend David Plouffe described it as like working in a submarine. And you look at the world through a periscope and you can very quickly lose your sense of touch. You know, Washington has its own interests and conversations that often are disconnected with the conversations and concerns of people out in the country. So these letters are like a lifeline. And there were many times when the president would come into a policy meeting and say, you know, I got this letter and I’m really concerned about it, and it would change thinking about policy. So being in the mailroom was a hell of a place to start. Yeah, but you were determined not to stay in the mailroom. And ultimately, you went off to graduate school. You went to the Kennedy School at Harvard. What, what did you hope to learn? Did you know by that point that you wanted to be a speechwriter?

No, I knew by that point, I actually wanted to be, I’d finally been promoted to legislative aide, so I had my own little portfolio. But as the only legislative aide without an advanced degree on Kennedy staff, there were some other Senate offices just running circles around me, people who had been doing it for 30 years. And I actually went back to my boss and said, Listen, I’m not doing the senator a service here. And so I thought-

Did you think you could get ahead in the organization by going to the Kennedy School?

I thought it would be easier if he wrote me a letter to get into the Kennedy School and true to his word, he said, listen, if you get he didn’t know the name of the test because like, if you get the if you get the average on the test, the school test, I’ll write you a letter. And so I did I got a 519 on the GRE and he wrote me a letter, but I assumed I needed a, I finally needed to get that numbers background. And the MPP program there had a deep background in economics and statistics, but it was also during the Kennedy School when the Obama campaign came calling about speechwriting. And I changed my course, because I had been I had written a few speeches for Senator Kennedy at that point. He didn’t have a speechwriter. So you just kind of wrote for your area. But I had been on the Senate, on the floor.

So he didn’t have a speechwriter. One of the one of the most celebrated speech makers of our time.

He had he had a legislative director who’d been with him for 40 something years who just edited the heck out of every speech to get it where it needed to be. So he was he was kind of like a chief speechwriter, even though he didn’t write anything for him. But but what really sparked my interest was I was on the floor in 2004 at the convention when Obama gave that speech because I was working for Ted Kennedy. We all got to go up for the week. And just that changed my life.

Did that, did you say I want to work on a speech like that?

Yeah, right away. I wanted to work on a speech like that. No, the first speech I wrote for Senator Kennedy was a floor speech, you know, for the 100 people at home watching C-SPAN2. And it’s not particularly good. I still have it. But but to watch somebody read what you’ve written out was electrifying, you know? And I called my parents. It was like, turn on C-SPAN2. And it was just really, really exciting. And I got to write a few more for him over time.

They found C-SPAN2 in time to see your speech.

I think my mom actually, like, emailed back, what channel is C-SPAN2?

So the Obama campaign called, I think. Stephanie Cutter, a mutual friend of ours suggested that you, who was very close to Ted Kennedy, suggested that you check out the Obama campaign. So you had minor speech writing experience. But you applied for that job. Favreau is that who hired you?

Yeah so, jon Favreau and I shared a mentor in Stephanie Cutter. She was Kennedy’s communications director when I was there. And then she was Kerry’s communications director in the ’04 campaign. And she connected us. And I think what mostly helped me get that job was that Favs was just drowning. You know, he was the only writer at the time. He hadn’t hired Adam Frankel yet.

I remember. I was I was the one who was drowning him.

Yeah. And he he said, look, we can’t pay you, but if you want to come out and intern, get out here.

Mm hmm. And what was that experience like? I mean, I know what it was like for me, but what was it like for you and how did your, how did your writing evolve through that campaign?

Well, it was terrifying because I and I never I don’t think I’ve ever fully shaken the idea that I’m a bit of a dilettante who doesn’t belong here. You know, I’d probably written ten speeches in my life, and here I am driving out to Chicago, which was awesome to work on the Obama campaign. So on the drive from Boston, I listened to both of his books on tape to just try to get down his voice, get down his worldview. I never met him on the campaign. You know, experience was obviously than yours, you were traveling with him all the time, but he was only in Chicago maybe three times while I was there and came in. He’d address the staff, but then go into high level meetings with you and Plouffe and everybody else. The first time I met him was in the Oval Office. I won’t skip too far ahead, but so the campaign was really the first thing I wrote for him on the campaign was his opening statement at the NAACP debate. There were not still nine candidates in the race. And just to watch that was incredible. And then you just kind of bone up quickly on every issue under the sun and Favs was a patient and dedicated mentor who would, you know, make detail that it’s the speech. Walk me through, not just what Obama would want to say, but why he would want to say it and kind of get us all on the same page with the campaign messaging.

You went to the White House with, and there was a, I mean, I’ve said this many times that I had a lot of wonderful experiences in the White House. But the the consistently great experience was meeting every day with the speechwriters or the wordsmiths, as I called you guys. And it was it was I don’t think I think Rhodes may have been 30. Everybody else was in their twenties.

Ben was the grizzled old man at 30.

Yeah. Favs was 26.

He was younger than me. A year younger than me.

Yeah. Heady for you guys.

It was exciting and terrifying because you walk in there and then the economy is falling apart. You know, it’s.

Wasn’t your fault, by the way.

Thank you. Yeah, but suddenly you’re assigned a speech on housing policy, and I’ve never written about housing policies. You have to find somebody at Treasury or upstairs in the NSC to explain it to you and. And then write it in the speech and the president go out. And it was like drinking out of a fire hose for a long time and really exciting and heady, but also kind of scary, too, because our own families were dealing with that at the time. Everybody was.

Yeah. But you guys, I mean, the I would say the first ten or 15 minutes of those meetings were basically a lot of jokes.

Yeah, Romper Room.

Yeah. Which, it was like a writers room.

We were very punny.

Yeah, yeah, I enjoyed that.

Well, I’ve kept that tradition going. You used to, you know, you kind of raise your eyebrows, but not look up from your BlackBerry and wish us all, hello.

That hasn’t changed.

Hello, wordsmiths. Whenever you came in, you know, once you left and I became chief, I did that every morning with my speechwriters, and I still do it every morning with my students.

We’re going to take a short break and we’ll be right back with more of The Axe Files. And now back to the show. You rose through the ranks. You were appointed at some point, deputy Chief Speechwriter. I left the White House in January of 2011. One of the last things that happened when I was in the White House was the horrific shooting in in Tucson, Arizona, of Gabby Giffords. Congresswoman Giffords, the president went down and gave the eulogy or she spoke at a memorial service for those who had died in that shooting. Obviously, Congresswoman Giffords mercifully survived, miraculously survived. And there was one and I remember this very well, because everybody said after the speech, like, who wrote that speech and this, I just want to read a couple of paragraphs of this. I want you to talk about it. He was talking about a nine year old girl named Christina Taylor Green. And Christina came out to see her congresswoman and was was shot and killed. And he said Christina was given to us on September 11, 2001. One of 50 babies born that day to be pictured in a book called Faces of Hope. On either side of her photo in that book were simple wishes for a child’s life. I hope you help those in need, red one. I hope you know all of the words to the national anthem and sing it with your hand over your heart. I hope you jump in rain puddles. And then he said, if there are rain puddles in heaven, Christina is jumping in them today. I get verklempt even when I read these words today. And here on earth, we place our hands over our hearts and commit ourselves as Americans to forging a country that is forever worthy of her gentle, happy spirit. Tell me about that. That particular because that is the kind of thing that that makes a speech memorable, powerful, meaningful. And I know it’s the sort of thing that you as a speechwriter are looking for to give that depth of feeling to a speech. Tell me about how that came about.

Yeah, my we saved this for the end of the speech after he’d, you know, in a eulogy, he usually takes time to remember all the victims. And in this one, there were a lot. But then also kind of instruct Americans as to what we’re supposed to do now that they’re gone, what are our responsibilities? And I my favorite part is even before that section you’re reading, where I changed up the language so that it wasn’t really the way Barack Obama would talk, it was the way that a little girl might talk that that she had gone to this event and she had just run for student council. And she thought that, you know, she wanted to see her congresswoman, someone she was sure was was good and pure and important. I wanted to describe what democracy might have looked like to a nine year old. And then we let her down and thought about how he might want us to see the world kind of undimmed by cynicism. And then Kyle O’Connor, who was our junior speechwriter at the time, found this book. I still don’t know how this faces a Pope book with her in it. And that’s what the power of good research couldn’t do. I mean, it just it just lent itself to this extraordinary story. And then how I think about speeches constantly, even if I’m not at my computer, they’re just always in my head. It makes me an awful dinner companion when I’m trying to think through arguments, and I just, I’ll realize I haven’t been listening to a word the other person has said. And I remember that line came to me-

I know we’re having dinner later, so thanks for the warning.

That line about rain puddles came to me that morning as I was getting ready for work. And the first thing I just I grabbed my BlackBerry and I emailed it to myself. And then when I get to work, we’ve it into the speech and that and that gets me too, you know, if you watch the last couple of minutes of that speech, it is it is something.

Yeah. Yeah. Well, anyone with a beating heart, I think, would feel the same. The same way we all think of our kids and grandkids. And let’s talk. You became the chief speechwriter in 2013 when Jon Favreau left. I want to talk about this wonderful book, “Grace: President Obama and Ten Days in the Battle for America.” There are so many things I love about the book, but one of them is it really does give you a sense of what goes into writing a speech. And one of them is that. The letters, the history, the hidden the hidden revelatory story. And you say research is I mean, I’m sure you put a premium on that in the staff, put a premium on that.

Mm hmm. I read constantly in the White House, not just custom tailored for each speech, but just just all the time. Everything I could, because each of us as individuals is not the font of all wisdom. We don’t have a monopoly on good ideas. I’d get them from anywhere. And then just try to improve on them. You know, for for the Selma speech I used to start the book, I read part of the Taylor Branch trilogy just to really get in the mindset of, I wanted to know what the marchers were-

Trilogy on the Civil Rights Movement.

On the Civil Rights Movement. I wanted to know what the marchers are doing that morning to get ready and prepare.

This was the speech marking the 50th anniversary of Bloody Sunday.

And it’s just doing that kind of reading is so important because empathy is really critical to speechwriting, super critical. You want to-

It’s kind of important to governing to, I would argue. But yeah.

That and a sense of shame I think are missing from our politics. But but there are limits to empathy you can imagine, right? For Tucson and Newtown. You can imagine what it might be like to lose a child. But if you don’t have children yet, it’s a stretch and you need to talk to people who do. I have one now. So I think I finally get it. But but if I was writing about anything that was outside my own lived experience, I would make it a real point to read up or talk to the president or talk to somebody else and try to get into the audience’s head first.

Talk about the the why you chose. I know this book has been in your head. You talk about being in your head, which obviously is an expansive place. You you you’ve talked about this ten days and this book. You were helping President Obama on his memoirs, you know, but in all during that period, you were saying, let’s get this book in my head that I really need to write. And it was about these ten days. You were in the White House for-.

2922 days.

Yeah, but who’s counting? And you chose these ten. Why did you choose these ten?

It’s, I mean, on its own, you’ll remember all of the stories and all of the all of the events in this book. You won’t remember that they all happened in the same ten day span. I mean, that in and of itself is a story that demands to be told. And part of me wanted it to be this book that lives through history, that so that someday my daughter reads this and her generation reads this and goes, wow. I remember someone wrote, I can’t remember who that. It’s just it was too far fetched for an entire season of the West Wing. Everything was covered in these ten days. But every event of those ten days also say something profound about America. They began, day one was the shooting in Charleston, where a white supremacist walked into a Black church. He’d been self-radicalized and obsessed with Confederate iconography and murdered eight Black parishioners in their pastor during Bible study. And then I get into the workings of the White House too, how to how do we snap to, does the president gave a statement the next morning? What do we say? What what is the president supposed to do in that situation? How do we prepare it? The families of the victims forgave the killer the day after that, which was just truly extraordinary on live television. We’re all watching it with our mouths open and that kind of changed the tone of the week, I think, you know, I don’t have data to back it up, but but it changed things in the White House. President Obama did not want to go give a eulogy. He didn’t want to speak.

Explain, why?

We had done over a dozen at that point after mass shootings. And this goes back a few years, the shooting in Newtown, Connecticut, where 20 little kids were murdered in their classrooms, along with six of their educators, was right after he’d been reelected. And he put aside his second term agenda right out of the gate to try to do something about guns, because it was just, what, an abdication of leadership that would be if he didn’t. And he had a little boost by Joe Manchin and Pat Toomey, who’s a who’s an arch conservative from Pennsylvania with an A-rating from the NRA. They both had one. They decided to work together on a background checks bill. And even though we knew the odds in the Senate would be long, that gives you something to try for. And so we traveled the country for a few months. He made it a centerpiece of his State of the Union address. Big, emotional, powerful ending. And in the end, in in April, it failed. It didn’t just fail. Republicans blocked a vote on it with the parents of the Newtown kids watching from the gallery. And that’s about as cynical as I’ve ever seen Barack Obama. Yet he went out and spoke in the Rose Garden with those families. I handed him a draft of the speech and he said, look out, I’m going to use this as a as a template, but I’m just going to wing it.

This, was this the, were these the remarks where he literally cried?

That was the day, that was the day of the Newtown shooting when he cried in the briefing room.

Day of the Newtown shooting. But there was real anger.

Yeah.

That day you know he’s, as you know.

Unvarnished.

Yeah but he’s he’s remarkably composed at all times and this was a time when he he just as you say, let it let it rip.

Yeah. And he came in after that speech into the outer Oval Office, which is this room just off the oval where his assistants sit, and he was almost yelling once the door closed, he said, what, what am I going to do the next time this happens? What am I going to say? I don’t want to speak. If we’ve decided as a country that we’re not going to do anything about this, then I don’t want to be the one who.

Offers thoughts and prayers.

Yeah. And just lets the country, gives the country the signal that it’s okay to move on before the next one. And I wondered if he’d hold true to that after Charleston.

But there was a moment in these ten days when you weren’t sure whether he was going to speak or not.

I mean, I got to confess, I was relieved when he didn’t want to because I didn’t know what to write after this one. And we knew this, this one’s much more charged than usual because it goes right into our oldest wounds, you know, goes right into race. And, you know, the Confederate flag was omnipresent, you know, in that shooting and in the days afterwards. But what those families did changed the way he was thinking about it. But also, you started to see some Republicans in the South come out against the flag for the first time. Strom Thurmond’s son, who was a Republican state rep in South Carolina, said it’s time for it to come down. The Republican governor of Alabama just quietly ordered it to come down over the statehouse and it mass retailers said we’re going to stop selling it. And things started feeling a little different than usual after a mass shooting.

And we should just say parenthetically, because the great thing about the book is that it’s sequential. So you do get a sense of of what each day was like. And the Supreme Court was considering two extraordinarily important cases at the same time. You did not know how the Supreme Court was going to rule. So you’re managing a staff that’s trying to write multiple scenarios for these events. Talk about the Supreme Court cases.

I had this great team of speechwriters. And so we we we would find we knew that the Supreme Court was looking at Obamacare for the second time and marriage equality. And it turned out that there were multiple options for each. I mean, we find out the same time as everybody else in America. You know, we had a lawyer in the courtroom.

That was in the days where they weren’t leaked in advance.

That’s right. We had a lawyer in the courtroom, but we would just find out by watching cable news. So you don’t want to make America wait several hours for the president to speak after something that big. So we prepared basically win, win and lose remarks for each. And then the lawyers came in. They’re like, actually, there’s there are four different options for each. I’m just like, get out, get out. So we were working on those two. But again, those go to something fundamental about America. You know, our, if if Charleston was all about race and whether or not we’re going to stand up to white supremacy and stand up for equal rights. These cases were about does this country guarantee some measure of financial security and health insurance to poor people and working people? Does this country, are we going to allow our gay brothers and sisters to get married or are we going to deem them some sort of second class citizen? All these questions were just coming to the fore at once in these ten days, and we had to write about them the entire time.

So returning to the speech in Charleston, you you describe in the book sort of agonizing process of trying to figure out what to write, including sleepless nights, long strolls, cigarettes.

I’ve quit, now I have a daughter.

Good.

My mother found out that I smoke from reading this book, and I knew she would and it would break her heart.

You deceived her this long?

Yeah.

Talk about the evolution of that speech and describe, this was the last sort of event in this book, the Supreme Court, that you flew off to Charleston when the the day the Supreme Court ruled on on same sex marriage. But the speech sort of, this speech was a particularly difficult speech in some ways those speeches, given the fact that they came out as as you hoped, as the president hoped, were easy to write. This one was really hard.

Really hard. And I’m very honest in this book, too, about what a challenge it is to write for him in general, let alone on something of this important and all these different third rails in one speech. It helped that the mood in the White House was slowly lifting over the course of the week and just the way the country’s conducting itself. And then suddenly Obamacare wins again and then marriage equality becomes a reality. And a bunch of our colleagues, you know, were suddenly told, you can get married, which which we always knew should be true. But to finally get it was a huge relief. But I’d been struggling with this speech all week long. I’m glad you mentioned the all nighter. It’s one of my favorite passages in the book just describing how weird an all nighter in the West Wing is. But I knew that the draft I’d been working on wasn’t there. And he’s talked about this publicly, too. He talked about on the Springsteen podcast. He did. I knew it wasn’t there and he hadn’t given me much to go on. And he knew that, too. But it’s, you used to have a phrase that just drove us insane when you’d read a draft, and you’d say, it was, what was it about the runway? It was like, I don’t think we’re landing on the runway or-

I don’t remember exactly. But yes, I used to send you guys back to the drawing board quite a bit.

Yeah, right. I think we’re undershooting the runway here, something like that. We’d all just go, ugh, Axe Yeah, but I knew it, but I was out of time too. And so I gave it to him Thursday evening and I’d agonized over it for three days. He calls me back to the White House 3 hours later, 11 p.m., and he tore up the last two pages in their entirety, which he’d never done to me before, and he’d rewritten them in 3 hours after I had three days. And they just soared. He took, I had the phrase Amazing Grace, and that’s where he started tearing it up. And he wrote out the lyrics. And he, more importantly, used the lyrics to build a structure for the back half of the speech, which was it’s one of those things where in retrospect, I just kick myself for not thinking of it because it’s beautifully simple. But I just, I’d been in my own head all week long writing about, I was terrified, writing about race and the Confederate flag and guns coming from him to a country that was a little bit on edge. But he was, this was one of the things that made him such a great boss. He could have been angry at me, you know, he could have sent it to somebody else and just excised me from the equation entirely. He sat me down and walked me through it and it was the first time I ever apologized to him for not hitting the mark. But he he said, look, brother, we’re collaborators. You know, you gave me what I needed to work with here.

Which, I don’t know how many speeches- you guys were superb speechwriters. I don’t know how many speeches we gave him, knowing that the speech was was in A-minus, A speech, and that he would make it an A-plus speech and that he would buff it up. But that is, it’s, I mean, you know, politics you always like to say, good speechwriters say, well, that’s really his work. But he really there always no matter how good you were, there always was this sense that he’s the best writer in the group.

That’s what made it so hard to write for him. Every time, we knew he just wanted something to work with. That wasn’t enough for us. We wanted to impress them, you know? We wanted to prove that we deserve to be there. We all suffered from some form of imposter syndrome. And he made it abundantly clear a lot of the time that we should feel that way. Not always. There were plenty of times where he’s like, I don’t know, just, you know, just write something. But not on the big stuff. On the big stuff he delivered. And so you were talking about the final morning, you know, where I-

Before, before you get there, that speech you that inspired you in 2004, you know, I was working with him on his Senate race. And, you know, we conspired to to get the keynote speech. He was just a state senator from Illinois, but he had been nominated for the Senate, the US Senate. And we really campaigned to get him the speech. And and then we had long negotiations about how much time they were going to give him. They said 8 minutes. We said 28, I think it was 17. And as you’ll appreciate as a good speechwriter, the 17 minute draft was probably better than the 28 minutes.

Oh, and harder.

Yes. But he was the author of that speech. I mean, we made small suggestions. We did some of the editing because he refused to cut as, he didn’t want to do it.

He’s told me several times he wrote that himself.

Yes, Yeah. And I’m here to attest to that. I’m here to attest to that. And as you get you know, because I used to say to everyone, go back and read that that’s the foundational kind of statement of values and principles for Barack Obama. But really breathtaking, you know, and I, working for him, got this speech and I said, my God, this is going to be one of the great convention speeches of all time. Anyway, that morning-

Yeah. I mean, it’s important that you just said all that. He is our chief speechwriter. I’d say that several times in this book. I think people have seen enough of Pete Souza’s photos to know just how much he works on this stuff, and it’ll all be in the library, just down the street someday for people to look at. And I can’t wait.

Yeah, yeah. Unless. Unless he’s spirited some off and hidden in his basement.

Don’t. Don’t do it, Eric Schultz is going to call you in 5 minutes. So there you know, I’m I’m both discouraged and fired up by what’s happened with with the speech. And I’ve slept 3 hours in three days. And I was working on a speech right through 10 a.m., which is when decisions come down. I forgot to turn my TV on to see what would happen with marriage equality. We knew that was going to be Friday because the court likes to be dramatic and hold them for the last day. And I start hearing whoops and cheers from all over the West Wing and I just know that we won and you turn it on and you see and by we, I mean America, not Barack Obama You see these joyous scenes at the Supreme Court and like, you can’t help but get a little bit choked up.

We’re going to take a short break and we’ll be right back with more of The Axe Files. And now back to the show.

So I go up to see him and a young woman on our team named Saridah Perry had drafted his marriage equality remarks for the morning and he goes out and did some beautiful ad libbing on it, too.

Yeah, I want to just put a pin in that, because one of the things that I one of the pages I folded over in this book was from that, if I can find it, it may be that I can’t, hold on. You write, he hits the last the last line, and you write and you’re about running for the helicopter to go down to South Carolina and you write, but he kept going. I stuck my head and watched. It wasn’t rare that he would adlib. He’d do it all the time. It was rare that he’d do it when there were no further words on the screen to return to. He was on his own here. I was curious as to where he’d fly and how it land this plane, and then his words, that’s the consequence of a decision from the Supreme Court. But more importantly, it’s a consequence of the countless small acts of courage of millions of people across decades who stood up, who came out, who talked to parents, parents who love their children no matter what, folks who are willing to endure bullying and taunts and stayed strong and came to believe in themselves and who they were and slowly made an entire country realize that love is love. What an extraordinary achievement. What a vindication of the belief that ordinary people can do extraordinary things. What a reminder of what Bobby Kennedy once said about how small actions can be like pebbles being thrown into a still lake and ripples of hope cascade outwards and change the world. Those countless, often anonymous heroes, they deserve our thanks. They should be very proud. America should be very proud.

You just read that about ten times faster than he did at the time.

Yeah. And he had to catch a helicopter.

He spoke even more slowly than usual. And I still to this day, believe that he was genuinely moved, that the country had come so far, so fast on on a civil rights and equal rights issue. And I asked him about that once and he said no, the reason I was talking so slowly is I was just tired from being up all night rewriting your speech. But but I knew that wasn’t true because he gave it back to me at 11 p.m. and he was probably up for several more hours doing something else. I really believe he was genuinely moved in that moment. And then so the military is precise. 5 minutes later, the helicopter lands on the South Lawn and we’re off for Charleston.

Yeah, a remarkable ad lib that speaks to his, the quality of his thought, but also his command of language. What you found out on the way out to Charleston is that he also had some command of music, because you wrote the speech and he said to you guys on the plane, on the on the on the helicopter, I may sing, and I think everybody remembers that.

Yeah. He said, if it feels right, I might sing it. And I just I was so tired. Just, like, normally I’m risk averse. I will I will just instinctively find reasons why you shouldn’t do something. But at that moment, we’d been it had been a joyous morning already, and I hadn’t slept in days, so I was just like you do you man, you know, go for it. And once you see, he understood the AME Church, he knew that they would be there for him. He knew that they would jump in and join him. And when you see it, you know, it’s it’s just not a question.

What was it like? You write about this, but watching that actually happen, I mean, I remember watching it from a thousand something miles away and how moving it was. But to have been part of this process and to see it actually happen was extraordinary.

I was about ten miles away. I stayed on Air Force One. Because he had made more edits to the speech and I didn’t want to risk the wireless cards not working en route to the church or to the arena. So I stayed behind, made the edits, and, but there was for me, selfishly, there was something kind of just nice and being alone and getting to watch it on television and just let all that pressure kind of pour off my shoulders.

And not a bad plane.

Not about plane. And I was watching him on TV and he he paused for 11 seconds before he started singing. And I knew I was going to sing, but I started immediately panicking that everyone at home would think he was missing a page, like a page wasn’t in there. But then he collected himself and started to sing.

Yeah. What did you say to him when he came back?

Well, I asked him what the pause was all about. You know, if he’s trying to create some drama and he goes, No, man, you know, what the thing about Amazing Grace is and I said, obviously not. He said, You’ve got to start low. Otherwise when you get to a wretch like me, your voice cracks. So you got to you’ve got to really put your diaphragm down and get into it.

I would be remiss if I didn’t mention that you also, interwoven through this, was your courting of your now wife, Kristen, who was a research director at the White House, which is, this, if you were going to write a situation comedy, you would write about a romance between the chief speechwriter and the research director, whose job it is to poke holes in everything that the speechwriter writes.

It was her job to tell me I was wrong multiple times a day, every single day for seven years.

And you guys thought this was good practice for marriage?

We’re still married. Yeah. We got our squabbles out of the way at work. But I write about her because she was my hero. She was, she was the only reason that I could keep writing at that level for that long. And that was true about everyone in our White House. This sounds like such a weird thing to say now after the past several years. But we loved each other. We were all forged during that first campaign and that more people stuck around for eight years than any other White House, because we loved each other. We lived together. We got married to each other. I joke with the president now that he’s got he’s got dozens of little grandbabies across the country from people who’ve met and got married by working for him.

Yeah, I just had a a new grandson this week, and he was one of the first people I sent a picture to.

Oh, he loves that. Loves that.

I want to just two things before we before we finish. Personal about your, about the role of being a White House staffer generally, speechwriter, because of the intimacy of your relationship, you literally inhabit someone else’s head and you become their their wordsmith. And to do that, you really have to have a mind meld. You did that for eight years. More than eight years, really. Because in the campaign as well, you were a young guy when you started. You had a few gray hairs when you when you left, and then you worked for him for several years more. What are the challenges of that? You’re obviously, everyone who’s listening to this podcast can see you’re an incredibly bright, thoughtful, fluent person in your own right. But one has to sort of subjugate all of your own identity in some ways to the principal. How do you how do you deal with that?

It’s hard. It’s hard. I had a lot of anxiety dreams and still do sometimes, usually about him wanting to know where the speech was. And I didn’t know that there was one or it’s not ready, or. But getting into his head was always a complicated task. You know, not just because we had different upbringings, but he he had this moral imagination to him that that is what really took the speeches to a higher place than I could reach. And it was a challenge. And the challenge of writing this book was actually breaking myself of writing like him. Trying to write differently. That was really difficult. And then when I went back and reread the first few chapters, they sounded like him, and I went back and rewrote those towards the end of the process.

Was there a sense at some point, and I’m maybe tipping my mitt, because we’ve had conversations, but just of, okay, I got to get on with the rest of my life and be Cody Keenan now, not the president’s speechwriter.

He would tell me that too, though. He would be, he would he would joke- even though he asked me to stick with him, he would say, you know, it’s time for you to figure out what you want to do and get out of here. And that’s where this book came in. I knew I didn’t feel good starting this while he was still paying me to write about him. So I waited until that was over. But it I’ll confess, I really wanted to prove that I could do something without him. It helped that he tweeted about my book. I’ll gladly take that. But. But, you know, I’m proud of this book for a lot of reasons. There are a lot of different reasons. I wrote it. That’s that’s the private one to me. And he read an early copy and sent a really nice note last week. And, you know, that means that means everything.

Yeah. And you’re also you’re now running Fenway Partners.

Fenway Strategies.

Fenway Strategies. Sorry. Writing speeches for a whole bunch of people, managing a staff again. You’re teaching speech writing up there at Northwestern, as we said. And you have a baby.

Yep. Gracie.

And the baby’s name is Grace.

Yeah. She and the book were born at the same time.

Yeah.

She’s, you know, she’s awesome. I miss her while I’m while I’m traveling. But she, you know, they’re both named after the concept, obviously not each other. But she was we found out we just moved to New York two months before the pandemic hit. And then we found out Kristen was pregnant two weeks before New York City shut down. And, you know, remember, it was terrible in New York City, 30,000 people died quickly. So that was a frightening year between the pandemic and, you know, kind of the all the upheaval after George Floyd, as exciting as that was, it was it was also, you know, unsettling. And the election, you know, that that went on for a while. She was, there’s no such thing as relatively easy pregnancy, but she was complication free. And every night she would, you know, just kind of kick at the same time like clockwork. And she was just, we didn’t deserve it. But she visited Grace upon us for that whole year.

Yeah.

So it was a no brainer.

Finally, I just want to ask you, you know, reading this book was a joyful experience. Thank you. And especially. Having lived some of that journey with with you and him. But I think anyone who reads this book will get a sense of idealism, sense of possibility, a sense of of hope, a sense that things can actually turn out the right way. But I also had a feeling reading it, that I was reading it through kind of sepia colored glasses, because these have not been particularly hopeful times. These have not been times of unity in our country.

So you’ve read the epilogue.

So how do you look at things today? How does someone who experienced this experience, who has seen progress, how do you view the world now and what do you have to say? We’ve got some young people in our audience. What do you have to say to them about the possibilities of the future?

Yeah. I don’t see a conflict between writing about this experience and that it was hopeful and sometimes joyful and fun to do this, to struggle to do good work in democracy with the realities we’re living through now. Because it wasn’t all sunshine and rainbows in the Obama White House either. But what I do want young people to take away from it is that it is a worthy endeavor. It’s worthy of your time and your energy. You will you know, you may never be lucky enough to join a campaign like ours or to work for someone like Barack. But boy, I shouldn’t say that out loud, like President Obama. But if you join a team that is committed to something bigger, it really can be fun. And another theme of this book is that none of these things that happened in those ten days were really his triumphs. You know, he pushed Obamacare through, but that was the result of a 100 year movement for universal health care. And we’re still not there yet. You know, marriage equality was a result of a 50 year movement for LGBTQ rights. We’re not done with civil rights. Out of the 2922 days in the White House, we usually went on happy if we just move the ball forward just a little bit. But all of those days are what contribute to the big victories, you know, and democracy can be really frustrating. Working in the White House, working Congress can be really, really frustrating. It can also be extremely rewarding. And, you know, if we did have more people in public service who thought that way, who cared, who knew that their efforts can make a difference, even if it takes a long time, we’d be in a better place. And it’s not impossible. And that also doesn’t gloss over all the very real work we have to do right now to preserve this democracy and keep it alive.

Or honest differences on issues that in a democracy you have to thrash out in good faith for us to truly make progress. The book is “Grace: President Obama and Ten Days in the Battle for America.” You said earlier, Cody, that we loved each other in the White House. I certainly feel that way about you. And as such, I’m incredibly proud of this work, and I hope that everybody reads the book. Thank you so much for being here.

Love you back. Thank you.

Thank you for listening to The Axe Files brought to you by the University of Chicago Institute of Politics and CNN Audio. The executive producer of the show is Allyson Siegal. The show is also produced by Miriam Fender Annenberg, Jeff Fox and Hannah Grace McDonald. And special thanks to our partners at CNN, including Rafeena Ahmad and Megan Marcus. For more programing from the IOP, visit politics.uhicago.edu.