President Barack Obama is seen in the Oval Office of the White House with Cody Keenan, left, his director of speechwriting, Ben Rhodes, the deputy national security adviser, and Jen Psaki, foreground, the White House communications director, on January 11, 2016.
CNN  — 

The idea for Cody Keenan’s New York Times best-selling first book came from a viral tweet storm.

It’s a genesis rich with irony for a man who rose to prominence as President Barack Obama’s chief speechwriter, toiling in a windowless West Wing office (the “speech cave,” as Obama’s wordsmiths called it) as he drafted tens of thousands of words for the 44th President.

But the fact it took two years for Keenan to fully grasp the depth of meaning captured by the weight and stakes of a 10-day period that shaped the country underscores the reality of his job – really any job – in a White House.

At the end of June 2015, Keenan and his team were responsible for drafting remarks on Supreme Court rulings that would eventually uphold the Affordable Care Act and establish the fundamental right to marry for same-sex couples – as well as remarks if the court had ruled differently on each case.

That was all happening as Keenan grappled with his own personal struggle – and Obama’s – to find the words to come to terms with the nationwide horror resulting from the murder of nine Black Americans attending a Bible study at Emanuel AME Church in Charleston, South Carolina.

Keenan is an engaging and almost charmingly self-deprecating Chicago native in person and has been traveling the country on a full-throttle book tour over the course of the last several weeks. But as I read the book on a recent Air Force One trip with President Joe Biden to the West Coast, I kept thinking of things I wanted to ask him that would expand on various elements of the book.

Full disclosure, I was covering the White House during the time period the book focuses on for Bloomberg News and knew Keenan at the time. He is unflinchingly loyal to Obama, who he continued to work for in the four years after they left the White House. He is a true-blue Democrat, even if that’s more of a backdrop of his experience than a defining feature.

But the reason I shot him a note asking to chat was to see if he’d dive a little deeper into his writing process – both in speechwriting and as an author – and into the rich portrait he paints of what it’s like to work in a White House at the most senior level.

A few days after giving his daughter, Gracie, the experience of her first Northwestern University football tailgate – his alma mater lost to Wisconsin by five touchdowns, which Keenan admirably acknowledged was a valuable early life lesson – we connected as I sat a couple hundred feet away from the building that he called his office for eight years.

CNN: Part of the reason I wanted to read the book is obvious - I was covering the White House at the time, it was a tsunami of history and news and I was kind of intrigued to see it from your end. But I think the more salient thing for me is that I’m fascinated by the process, just the insight into how anyone at a high level approaches their job – there’s so much you can learn. And there’s an extraordinary amount of detail in here on exactly that. But one thing I kept wondering throughout was, man, were you just taking copious notes like 24/7 while you were here?

Keenan: I was not, I promise, because when we first joined the White House – this is gonna sound like a joke, but it’s not – they were very adamant that any notes you take, any journals you take belongs to the National Archives and not you. So, they actually cautioned us against keeping notes.

But one of the lucky things is within the Oval Office, I would transcribe all of my conversations with the President on my laptop, because that’s how I wrote my speeches – I would ask, and prompt, and get him going.

So, all of our conversations in the Oval are verbatim, just because I would type it down super-fast because I needed that material for speech writing. So, I did have those.

But the rest of it is memory – there’s a mix of emails to myself. But there was no notebook or journal or anything like that.

CNN: As you’ve talked to people since the book has been out, what are the elements that you hear … from people who don’t understand how this place works, that they’re most surprised about? Beyond the fact that you worked in a cave.

Keenan: A lot of people been surprised by a few things. Number one, and this is gonna make you roll your eyes, but how much we all liked each other, which I think is really rare in any company, any business, let alone a White House. We were family – I mean literally, I met and married my wife (Kristen Bartoloni, the White House research director) there.

But also, that it’s just a slog. And I wanted to convey the struggle to do good work. Because you don’t just ride into town and do everything you said you were gonna do. It is really, really difficult. And for the 2,922 days we were there, a good night was when you could go home just feeling like you’ve moved the ball forward a little bit. Because all of those inches eventually add up to a touchdown.

You know, the Obamacare ruling, the marriage equality ruling – those were the result of not just years of our effort, but decades of other people’s effort. Democracy is hard. That’s what I wanted to convey.

Also, there’s still people out there who aren’t convinced that Barack Obama was an active speechwriter. He was our chief speechwriter. He was involved in every speech - you know this from being there. Writing for him was very, very difficult just because he was so good at it and expected a lot from us. And we expected a lot of ourselves we tried to get in the first draft.

CNN: I wanted to dig in on that, because you’re very candid about the kind of “imposter syndrome” that almost seemed pervasive. The reason it struck me is one, because I think I identify with it, and I think many rational people probably would. But two, in this town where everybody acts like they know everything and often know nothing at all, you don’t usually see it laid out in such a detailed manner.

Did it come from who you were working for and his reputation as a writer and orator? Or is that just you generally?

Keenan: It’s mostly working for him and never really believing I earned it.

But we all felt that way, whatever our jobs were. None of us felt like we had earned the right to be there, or just deserve to be there. We all had impostor syndrome – and I think that’s a good thing. Because that is what constantly pushed us to do our best work and prove that we deserved to be there.

And you know, maybe this is a little unfair because I don’t actually know any of the Trump people, but I never got the sense that they felt the same way. I always got the sense they felt like they were entitled to be there and deserved to be there. And I think as a result, the country didn’t get their best effort.

CNN: You get into it a little bit, but the process of working underneath (Obama’s first chief speechwriter Jon Favreau) to being “the guy” – what was that like? How did you become the heir apparent?

Keenan: The great thing about Favs was for all of his fame – and he became famous on the first campaign because Obama’s speeches were different, you know Favs was the wunderkind who dated actresses and was famous. But he never acted that way, he did not have an ego. Everyone wanted to be around him, but he was a patient and generous mentor who taught me almost everything I know about speechwriting.

The way it just kind of unfolded was when we moved into the White House, I was the junior speechwriter on the team and so I made myself a workhorse. I did like four speeches a week and just worked my butt off.

But I drafted the Tucson eulogy (for the victims of the 2011 shooting in the attack on Rep. Gabrielle Giffords), and (White House press secretary Robert) Gibbs outed me on the plane to everybody without my knowledge. We were flying back from the eulogy and some of the press corps asked, “Who helped the President with those?” And Gibbs said it’s Cody Keenan, and then he took the … step of spelling out my name to the press corps.

I still don’t know who asked, but obviously there’s a lot of Northwestern grads in the press corps and one of them said “proud Northwestern Wildcat.” We got back to (Joint Base) Andrews at like 2 a.m. or 3 a.m. or something, and I just slept in. I slept in till like 10 before going back to work. And I woke up to 300 emails and a bunch of missed calls. And that’s a little unusual.

And Savannah Guthrie was calling and trying to get me on the show and I was just like “what the f— is happening?” I didn’t know at that point that Gibbs had done that and that was weird.

Losing your anonymity is a little uncomfortable. And there were reporters calling my parents and my sister and I don’t blame them because you guys are just – the way this system works is you guys are desperate for news. But that was a little a little scary to lose your anonymity like that.

But shortly after that, Favs named me his deputy and I moved over (from the Eisenhower Executive Office Building) to the West Wing into an office with him. That’s when I got to start working with Obama more closely. It was a flight back from LA, Favs was with him on Air Force One and he said, “Look, I’ve been with you for eight years now and I think it’s time for me to move on.”

And Obama asked him, “Do you have anybody in mind to replace you?” And he said, “Yeah, I think it’s Cody.” Then Obama said, “I think that’s right.” It was as simple as that, but still, when he told me that when he got home, I was like, “You’ve gotta be kidding me!”

CNN: How did that change the dynamic of your relationship with the President?

Keenan: It’s hard to be speechwriter for somebody if you don’t spend a lot of time with them. And just the way the White House works, junior speechwriters didn’t get to spend a lot of time with him. Favs was good about making sure we got to if there was a big speech, but from then on, I was with Obama almost every single day. That’s really the best way to get into his head and be able to understand not just what he wants to say, but why. And that changed everything. I got email privileges to email him, I got walk-in privileges to the Oval and that just kind of vaulted me up the ranks, not just in title, but also as a better speechwriter for him.

Keenan, center, is seen during a ceremony for the unveiling of the official White House portraits of Obama and former first lady Michelle Obama in Washington, DC, on September 7, 2022.

CNN: You reference “the muse” in the book – the moments when the President fully engaged on a speech you’d drafted and really elevated something in his own voice. Was that a crutch as a writer? Could you count on that if you were stuck or was that a risk you couldn’t take?

Keenan: It was a risk and it always made me nervous when he’d say – and he didn’t say it often – but sometimes he’d say, you know, “We’ll see if the muse strikes.” And we were just like “Oh, no.” And sometimes it didn’t. But when it did, it would hit in a big way.

Like Charleston, you know, I’m very clear about this in the book, he just kind of tore up the back half figuratively. And fortunately, the muse hit really hard. The speech that I’d spent three days agonizing over, he re-wrote in three hours and that came from a mixture of things. The muse hit for him, it was what those families did, forgiving the killer. It was his correspondence with his pen pal, Marilynne Robinson, who I didn’t know existed. And it was the fact that the Supreme Court has ruled on marriage by morning and it just kind of gave him this open heart.

But, man, there were times when I would turn in a draft and be like, God, I hope he can make this better.

CNN: When he struck out the last two pages of the Charleston draft, I think you wrote that he just put a giant X through the pages – honestly, if an editor did that to me, I’d be ready to fight them. How do you react to that and not want to lose your mind?

Keenan: I wasn’t ready to fight him because I knew he was right. And I knew when I turned it in, and I told him as much, that I just could not get it there. And it was his idea to use the lyrics to “Amazing Grace” not just to sing, but to build the structure to the back half of the speech.

And again, it just sounds like Kool-Aid drinking, but this is the kind of boss he was he could have just given it back to me and said, you know, you need to do better. Or even worse, you could have just excised me from the equation. He could have given them back to Denis (McDonough, the chief of staff) or Valerie (Jarrett, Obama’s closest adviser), and just said, “give this to Cody” and not talked to me at all. But the fact that he brought me in, walked me through them and told me, made me feel better and said, “Listen, we’re collaborators. You gave me what I needed to work with here.”

I mean, just to take the little bit of time to do that makes all the difference in the world. It’s the difference between a speechwriter who loses his self-confidence forever, or one who just remains determined to keep doing better.

CNN: Which I don’t think is necessarily the norm in terms of bosses in DC – which I guess I always had a sense of because you guys are all still so loyal to him, but this was one of the better anecdotal demonstrations of it that I’d read.

Keenan: Yeah. It’s very rare in politics, but I think anywhere to have a boss like that. It’s just really special and makes a big difference to your team. We just had a wedding a couple of weeks ago, where two staffers got married to each other – Joe Paulson and Samantha Tubman – and Obama was there. You know, the fact that he flew across country just to attend their wedding is just to show you what kind of guy he is.

CNN: But was there ever a time you – look, you say it didn’t bother you when he would cross out two pages or have three pages of handwritten notes because you knew he was right – but was there ever a time when you thought he was wrong?

Keenan: It was pretty rare. But there were a couple of times, and he valued us pushing back on him. He liked it. He disdains groupthink. And it would really drive him nuts if everyone in the Oval would almost kind of nod and say I agree. I agree. Agree. He would find the person who didn’t, and he wanted to hear what that person had to say, and it didn’t necessarily mean he changed his mind, but sometimes he did.

CNN: When did you actually know you want to write this book?

Keenan: It’s interesting, not at the time. You know, you’re not thinking as you go through, OK, this is day six, you’re just living it with everybody else.

And it really coalesced for me on the second anniversary of day 10 of the book, which is marriage equality and Amazing Grace and the White House lit up like a rainbow. Trump had done something that morning, who remembers what at this point. He was just pissing everybody off with an 8 a.m. tweet, and I realized it was the second anniversary of those 10 days, so I did like a mini tweet storm to kind of remind people about what happened in those 10 days … and what we were capable of and it just kind of took off.

It was really like my first viral tweet and Esquire magazine wrote it up and that was the first time I thought that there’s a story here. I was still working for him. I worked for him for four more years and it didn’t feel right to write a book while he was paying me, so I didn’t start writing till 2021. But I started thinking about it in 2017.

CNN: Were you pinging ideas off him at all or sending him drafts throughout? Or did you wait until it was done to show it to him?

Keenan: I did. I told him all about it as I was thinking it through while I was still working for him. Then I left on New Year’s Eve 2020. And my wife got pregnant shortly after. Then the pandemic hit so everything kinda got put on hold. But I sent him a really early draft back in March and I took some risks. I knew that if there’s a book about him, it’s likely he’s going to read it quickly. And he got back to me within about four days.

If you think that waiting for him to get his feedback on a speech draft is agonizing, try sending him your book. But he sent back nicer praise than he had ever sent me on speech. And he offered one edit for the book, just one, that actually really did make it better, because he just can’t help himself.

But it was a relief to kind of get his stamp of approval, especially on the parts that I tried to be really honest about, which is what it was like to be a White speech writer writing for the first Black president I really wanted to make sure I didn’t get that wrong. And fortunately, to hear him say, “this is dead on,” was a nice thing.

Keenan is seen on "The Late Show with Stephen Colbert" on October 5, 2022.

CNN: I was struck by that specific issue when I was reading. You’re very candid about your efforts to grapple with writing about race – particularly for the first Black president – as a White guy from the North Side of Chicago. It’s really the backdrop of the way you thread together the process of writing the Charleston speech. Was there ever a moment where you’ve felt comfortable with that dynamic, or you felt like you understood his perspective and voice so well that you weren’t going to have to grapple with that reality?

Keenan: I think it’s related to imposter syndrome. And a lot of that actually became clear, too, after George Floyd, where we all tried to get better. And you can view yourself as being on the right side of these issues, but how do you really know if you’re actually doing injustice?

To be a speechwriter you have to be able to write for anybody and it requires a sense of empathy and to be well read. But what does a White kid from the north side of Chicago really know about inhabiting the life of a Black man in America? There just – there are limits to the imagination. And so that’s why we’re trying to grab him before those bigger speeches and be like, “Help me with the story I’m trying to tell. Am I right? Is my take right on this or is my life experience getting in the way?”

It helped that he was really our chief speechwriter, but he would also talk us through it and made sure that we were approaching these issues from the way he wanted us to approach them.

CNN: Just a couple more before I have to jog over to Pebble Beach (on the White House North Lawn) and be on TV and you probably have another dozen events for your best-seller. Do you feel like you got better as a writer as the years went on?

Keenan: Yes. You know, I look at my early stuff and I cringe. I still go back and edit some of our biggest speeches – that never goes away. I go back and edit my book, but I absolutely got better and that’s just a result of being around Jon Favreau, being around Barack Obama, being around my entire team – Ben Rhodes, Adam Frankel, Sarada (Peri) – everybody made me a better speechwriter. I’m very honest in the book, and I’m not just trying to be self-deprecating for self-deprecating’s sake. This was a hard, hard job. But I knew that by the end I was really good at it. That just doesn’t mean that you think you’re better than Barack Obama at this – you know you’re not. So, that’s what kind of always kept me on my toes and that’s why I stuck around for eight years.

CNN: You don’t mention the current president a ton in the book, but you do mention his decision to get out in front of (President Obama) on gay marriage and I believe the reference was he was kind of like Kool-Aid man busting through the wall to announce his view – I think I remember that correctly.

Keenan: *laughter*

CNN: But unlike some in the administration – at least at the time – who weren’t pleased at all, you describe it in a way that seems to convey you found it somewhat endearing. And the context very much reflects of how his close friends/advisers describe how he operates – he’d had a personal experience a couple of weeks prior and just answered the question with what he was thinking.

In that sense, how did you view him inside the White House when you were there, and how do you view him now?

Keenan: The marriage equality thing was just Joe being Joe. I never saw – I was never like really in intense national security meetings with Biden and Obama. But I never saw Joe Biden to be calculating. He just does what he thinks is right. The people that need him are really what move him. There’s no way that Joe Biden sat there and calculated, “I’m going to come out before the President on this.” He was just with gay people and their kids and was like, “you know what, this is the right thing to do.” And as probably the highest, probably the highest-ranking Catholic in America, at least in politics, that makes a big difference. So, I love Joe Biden. He just governs with his heart, which I think is a great place for a politician to be.

CNN: You also briefly mention Biden’s current (director of speechwriting) Vinay (Reddy) – you wrote he sent a thoughtful note to you before the Charleston speech. I’ve always had the sense that you have a similar approach to what Obama wanted, which is you’re just going to keep your distance from the folks that are in now because you dealt with plenty of people who thought they knew the best way to do things when you were there. Is that fair?

Keenan: Absolutely. It drove me nuts whenever I saw pundits on TV saying look, here’s what Obama needs to say, here’s what Obama needs to say. We’ll figure that out. The last thing Vinay needs from me is me being out there saying, “Here’s what Joe Biden needs to say.” He knows. To be a speechwriter, it is hard to find the words sometimes, it is hard to juggle competing audiences and competing interests. Whenever Vinay has asked me for help, I have offered it, but otherwise I’m not going to jump in there.

CNN: Last one, probably the most dangerous one: Do you feel like your reputation was bolstered or undercut by the admission that you listened to Taylor Swift’s “1989” on repeat while drafting the 2015 State of the Union address?

Keenan: I have met people on tour who have proven it has bolstered (my reputation). I’m a full Swiftie-man now. My daughter was born to “Folklore.” That’s the album Kristen wanted playing when she was in labor. And you know what, her song “The One” puts Gracie to sleep instantly, so I will always be grateful to Taylor Swift.