DC insider on the 10 most crucial days of the Obama presidency
Other than being able to string a sentence together, empathy is the most important quality in a speechwriter. The ability or at least the attempt to understand your audience, to walk in their shoes for a little while, even if empathy will never be a perfect match for experience.—Cody Keenan, Grace
Ten days in June 2015 were some of the most intense during the presidency of Barack Obama. The president was awaiting US Supreme Court decisions on the fate of the Affordable Care Act and marriage equality. And, on June 17, a hate-fueled white supremacist shot to death nine African American worshippers at a historic church in Charleston, South Carolina.
Chief White House speechwriter Cody Keenan focuses on this extraordinary period in his revelatory and lively new book Grace: President Obama and Ten Days in the Battle for America (Mariner Books).
In response to this perfect storm of historic events, Mr. Keenan drafted memorable speeches and a heartfelt and now immortal eulogy for Reverend Clementa Pinckney and other victims of the Charleston violence. And that address moved beyond a eulogy with the president’s powerful plea for unity and reconciliation and his surprising segue as he led the congregation and the nation in singing “Amazing Grace.”
In Grace, Mr. Keenan recounts highlights of his career as a speechwriter as he describes the tumultuous ten days. The reader immediately senses the demands of working for a president who was himself the former editor of the Harvard Law Review and among the most celebrated writers and orators of the recent history. As Mr. Keenan puts it, “To be a speechwriter for Barack Obama is f---ing terrifying.” Mr. Keenan worked “to his limits” in his high-pressure position to provide President Obama with the best drafts possible. And it’s obvious from Grace that the two men were gifted collaborators who worked together with great mutual respect and admiration.
As he provides a behind-the-scenes perspective on White House operations, Mr. Keenan introduces key presidential aides such as Valerie Jarrett, Jen Psaki, Ben Rhodes, Jon Favreau and his speechwriting team. He also intersperses the book with the story of his romance with esteemed presidential fact-checker Kristen Bartoloni, who often challenged and corrected his writing. They married at the White House in 2016.
By 2015, President Obama had delivered more than a dozen eulogies for the victims of gun violence, including for those who died in the massacre where Representative Gabby Giffords was seriously wounded in Arizona and the horrific gunshot murders of 20 children and five adults in Sandy Hook, Connecticut. Mr. Keenan wrote those eulogies as well as the president’s now famous speech honoring the fiftieth anniversary of the 1965 March on Selma for voting rights and those peaceful protesters including civil rights icon, Representative John Lewis, who endured a bloody attack by police.
Mr. Keenan writes powerfully of the pain and sorrow that he and the president experienced in addressing yet another mass shooting in June 2015, that time with the added dimension of racist violence. The description in Grace of the creation of the president’s address for the funeral of beloved Reverend Clementa Pinckney is a case study in collaboration in the speech drafting process.
During the same sad week, Mr. Keenan wrote statements for the president to deliver if the Supreme Court gutted the Affordable Care Act and ended marriage equality. We now know that those speeches on the Court decisions weren’t necessary. And the eulogy for Reverend Pinckney will be remembered as one of the great presidential addresses. Mr. Keenan concedes that this eulogy was his most difficult assignment after working on more than three thousand speeches for President Obama.
Mr. Keenan’s heartfelt and moving memoir Grace shows how a gifted president and his devoted team worked together tirelessly for a more fair, more tolerant, and more just nation.
Mr. Keenan is best known as an acclaimed speechwriter. He studied political science at Northwestern University and, after graduation worked in the office of US Senator Ted Kennedy. After several years in that role, he earned a master's degree in public policy at the Harvard Kennedy School. He subsequently secured a full-time position with Barack Obama's presidential campaign in Chicago in 2008.
When President Obama took office in 2009, Mr. Keenan became deputy director of speechwriting in the White House. He was promoted to chief White House speechwriter during the president’s second term. He also collaborated with President Obama on writing projects from the end of his term in 2017 until 2020. He has said that he wrote his dream speech just four days before Obama left office—welcoming the World Champion Chicago Cubs to the White House.
Mr. Keenan is currently a partner at the speechwriting firm Fenway Strategies and, as a visiting professor at his alma mater Northwestern University, he teaches a popular course on political speechwriting. Today, he and Kristen live in New York City with their daughter, Grace.
Mr. Keenan graciously responded by email to a long series of questions on his new book and his work.
Robin Lindley: Congratulations Mr. Keenan on your engaging new book Grace, a revelatory exploration of your work as chief speechwriter for President Obama at an incredibly turbulent time. Before getting to that period, I wanted to ask about your background. You majored in political science at Northwestern University. What sparked your interest in politics?
Cody Keenan: Well, I enrolled at Northwestern as a pre-med student. I wanted to be an orthopedic surgeon after a football injury forced a knee reconstruction. Chemistry 101 weeded me right out, though. I just wanted to take biology.
But politics had always been an interest. My parents often argued about politics at the dinner table – my mom was a Kennedy Democrat from Indiana; my dad was a Reagan Republican from California – and whatever could make them so animated was something worth exploring. One value they both hammered into me, though, was the idea that I should do whatever I could to make sure more people had the same kind of opportunities I did growing up – and by the time I graduated from college, only one political party cared about that.
Robin Lindley: Did you have academic or other training in speechwriting?
Cody Keenan: No. Writing was something that always came naturally, and I think that came from being a voracious reader. I won every summer competition at the local public library. You can’t be a good writer without being a great reader.
Robin Lindley: You interned for legendary Senator Ted Kennedy after college. Did your duties in that role include speechwriting?
Cody Keenan: Not as part of the internship, or even the first position after that. Three months as an intern got me hired to answer his phones. I ended up working for him for almost four years in four different roles.
In 2004, when I was on his staff for the Committee on Health, Education, Labor, and Pensions, the Democratic National Convention was in Boston, his hometown. We all took a week off work to volunteer. I was on the arena floor the night that Barack Obama gave the speech that made him famous. He walked into the arena anonymous; he walked out 17 minutes later a global megastar. It shows you what a good speech can do.
Once we were back in Washington, I must have talked about that speech a lot, because that’s when my boss asked if I could write a speech. I don’t know if he meant did I have the time or did I know how, but it didn’t matter – I lied and said yes.
Robin Lindley: Senator Kennedy was known as a great legislator in the Senate who could work across the aisle. Did you work with him or his staff on any significant projects? What did you learn from that internship?
Cody Keenan: As an intern, one of my tasks was to read and route mail that came to the office. Perfect strangers were writing a senator – often one who wasn’t even their senator – to ask for help. There’s an act of hope involved in that. Even when it was a tough letter to read, even when you could see that the writer had wiped a tear from the page, they hoped that someone on the other end would care enough to help. I learned right away just how important this stuff is.
Later, as a staffer, I worked on all sorts of legislation. Kennedy was involved in everything. Health care, minimum wage, education, immigration, the Iraq War, the response to Hurricane Katrina, Supreme Court nominations – we were always busy. And with good mentors, I learned that just as important as the policy itself was often the way you communicated it.
Robin Lindley: What attracted you to working for President Obama during his first presidential campaign in 2007? Did you work as a speechwriter before his election?
Cody Keenan: Well, what struck me about that 2004 speech was that he described politics the way I wanted it to be – as this collective endeavor in which we could do extraordinary things that we couldn’t do alone. His only speechwriter at the time, Jon Favreau, called me early in the campaign and asked if I wanted to join the speechwriting team he was putting together. I said yes.
Robin Lindley: What did you learn or do to prepare for work as a speechwriter for President Obama, one of our most celebrated American writers and thinkers even then? Did you go back and read works of some of the great White House writers such as Ted Sorensen, Bill Moyers, and Peggy Noonan? Did you read speeches by the likes of Lincoln, FDR, JFK, Churchill, and other memorable leaders?
Cody Keenan: I didn’t. I’d already read the canon of presidential hits, but to be a speechwriter for someone means writing for that specific person, helping him or her sound not like anybody else, but rather the best version of himself or herself.
Robin Lindley: I read that you didn’t personally meet President Obama until his first day at the White House in 2009. Yet, you had been working for him for a year and a half. What do you remember about your first meeting and your early days at the White House?
Cody Keenan: Yep – he visited Chicago headquarters maybe three times during the campaign. He was out campaigning! And when he did visit, it was for strategy sessions with his top aides and to address the entire staff at once, not to meet with his most junior speechwriter.
On our first day at the White House, he called me into the Oval Office because he’d seen my name at the top of speech drafts and he just wanted to put a face to the name. Those early days were drinking from a firehose: the economy was falling apart, millions of Americans had lost their jobs and their homes in just the four months before he took office, and millions more would in the first few months after. There was no honeymoon; we were busy trying to turn that firehose onto the fire.
Robin Lindley: Did you immediately start as a speechwriter once President Obama began work at the White House?
Cody Keenan: I did.
Robin Lindley: How does one prepare for a job that requires knowing the voice and propensities of the person they are writing for?
Cody Keenan: Well, I had a year and a half foundation from the campaign. I’d read his books to absorb his worldview, listened to the audio versions to absorb his cadence, and paid close attention to his edits. He was a writer. He was our chief speechwriter. And he was our top editor. I learned a lot just by poring over his edits to our drafts.
Robin Lindley: How did your relationship with President Obama evolve over his eight years in office? You wrote that working for this acclaimed writer could be terrifying. It seems he offered good advice to you such as having a drink and listening to Miles Davis or John Coltrane. Or reading James Baldwin. Did you see him as a kind of coach or mentor?
Cody Keenan: I was the junior writer on the team for the first two years, sitting across the driveway in the Eisenhower Executive Office Building. Then a series of high-profile speeches got me promoted to deputy director of speechwriting, and I moved into a West Wing office with Jon Favreau. Once he left after the second inaugural, I took over as chief speechwriter. So naturally, our relationship evolved – I went from seeing Obama every couple weeks to every week to every day.
I saw him as my boss. I guess as a writing coach of sorts. And sometimes even as an uncle or older brother who loved to dispense advice. He hosted my wife and our families and our best friends at the White House on our wedding day. It was his idea. He didn’t have to do that.
Robin Lindley: Are there other bits of President Obama’s advice that stick with you?
Cody Keenan: “Don’t impart motives to people.” That’s advice we could use more of.
Robin Lindley: Indeed. A big question, but can you give a sense of the speechwriting process? What sparks the process? Who is involved? What’s it like to collaborate with a team of writers and other staff?
Cody Keenan: He viewed speechwriting as a collaboration. He just wanted us to give him something he could work with. We wrote 3,477 speeches and statements in the White House, and believe it or not, he edited most of the speeches, even if lightly. But he couldn’t be deeply involved with all of them.
For any speech of consequence, though, we’d start by sitting down with him and asking “what’s the story we’re trying to tell?” Then the speechwriting team would talk over each speech, helping each other get started. Then we’d all go back to our own laptops and draft whatever speech we’d been assigned. The drafting was not a collaborative process. The revising was – with each other, but more importantly with him.
Robin Lindley: What’s the fact checking process for a speech draft before it goes to the president? It’s interesting that your future wife Kristen was one of the very diligent fact-checkers you relied on.
Cody Keenan: Yeah, she literally got paid to tell me I was wrong. Every day. For years. It was her team’s job to fireproof the president – to make sure he never said something he shouldn’t, with someone he shouldn’t be with, at a place he shouldn’t be visiting. They prevented countless alternate timelines where we’d have to do some cleanup in the press. They saved us from ourselves again and again.
Robin Lindley: Congratulations on your marriage to Kristen with the magnificent White House wedding. Your blossoming romance runs like a red thread through your book. You note that President Obama would stay up late at night to review and edit drafts of speeches he would give the next day. And you often received late night calls from him or met with him in the wee hours. How did those final hours work with a speech? It seems the president would often edit to the time of delivery.
Cody Keenan: He always edited in the wee hours of the morning. It’s when he preferred to work. It was rare that we were editing right up until delivery. If we were flying somewhere for a speech, he’d always go over it one or two final times on the plane. But he didn’t like chaos. In fact, the reason he edited so heavily, so often, was because he wanted the speech exactly the way he wanted it. Sometimes it was perfectionism. But it’s really just preparation.
Robin Lindley: What did you think when the president ad libbed or changed something from your draft as he spoke? I think you said something to the effect that he was a better speechwriter than all of his writing staff.
Cody Keenan: I loved it. I can’t think of a time I cringed at an adlib. He had a knack for it. It could be a little white-knuckled if he did it at the end of the speech when there’s no text for him to come back to. In that case, he’d have to build a new runway while he was speaking on which to land the plane.
Robin Lindley: When does humor come into the mix? Do you write for events such as the White House Correspondents Dinner? President Obama had some zingers for his eventual birther successor at these events.
Cody Keenan: Those were our most collaborative sets of remarks. The entire team would pitch jokes, and we’d reach out to professional comedy writers to solicit their help. We’d start out with about 200 jokes and whittle them down to the 20 funniest. Sometimes, none of your jokes would make the cut. You’ve got to have a thick skin.
Robin Lindley: And you and the other speechwriters did not use a template such as this speech is on the economy or this speech is political, so we’ll use the file template X or Y. You were responsible for more than three thousand speeches, yet it seems each speech was approached as a unique project.
Cody Keenan: Yes and no. We never used a template. But while each individual speech should tell a story, so should all speeches. What I mean by that is, we were mindful that every speech we wrote fit into a longer narrative arc – both of his presidency and his entire political career.
Robin Lindley: You worked for the president through his eight years in office. How did you come to focus on ten days in 2015 in Grace as the president dealt with the horrific 2015 mass murder of nine Black parishioners by an avowed white supremacist at Mother Emanuel Church in Charleston, South Carolina. The president then also was preparing to address two impending Supreme Court decisions that would determine the fate of the Affordable Care Act and marriage equality.
Cody Keenan: Yeah. People will remember all of the stories and all of the events in this book. They 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. In addition to a massacre carried out by a self-radicalized white supremacist, there was a very real chance that the Supreme Court would say no, people who work two or three jobs don’t deserve help affording health insurance; no, gay Americans don’t get to get married like the rest of us; all of those people are now second-class citizens. And the first Black president has to serve as the public narrator and provide some moral clarity for all of this.
Someone once described it as ten days too implausible for an entire season of The West Wing. But it’s also what those events symbolized and how they fit in the broader, centuries-long story of America – whether or not we’re actually going to live up to the ideals we profess to believe in. Whether we’re going to stand up to white supremacy, and bigotry, and people who profit from inequality and violence. And that week, the answers were all “yes.”
Robin Lindley: With the Charleston massacre, the president had to address another mass shooting and he was tired of giving eulogies after the murders at Sandy Hook and all of the other heartbreaking mass shootings during his term in office. How was his speech at Mother Emmanuel Church different from previous addresses? What was your role in creating this memorable speech? How did the speech go beyond a eulogy to become a message of reconciliation?
Cody Keenan: We had done over a dozen eulogies after mass shootings at that point. 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 what an abdication of leadership that would be if he didn’t. And he had a little boost by Joe Manchin and Pat Toomey, 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 April, 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. 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 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 closes the cycle every time with a eulogy that gives the country permission to move on.”
Ultimately, we did decide to do a eulogy after Charleston, and it was his idea to build the structure of the speech around the lyrics to “Amazing Grace.”
Robin Lindley: I think everyone was surprised and moved when President Obama sang “Amazing Grace” during the Charleston speech. Were you surprised or was that part of the plan for the speech?
Cody Keenan: That, too, was his idea. He told me on Marine One that morning that, if it felt right in the arena, he might sing it.
Robin Lindley: You now teach speechwriting at your alma mater Northwestern University. Do you have any other advice for prospective speech writers?
Cody Keenan: It’s fun, training a new generation of speechwriters and trying to convince them that public service is worth it. What I didn’t expect was that my students would end up teaching me quite a bit in return. There’s an impatience to their generation that mine didn’t have to have. Politics and the pace of change is now existential for them in a way it hasn’t been since schoolkids were doing duck and cover drills during the Cold War. They’re doing those duck and cover drills again because of guns. They can see an end to their future because of climate change.
And let me tell you, when they see a party more into policing books than policing assault weapons; when they see a party more exercised about drag queens than about climate change – they feel a real disdain there. I want them to harness it, though, in a productive way. And part of that means telling them the truth. To tell them that change has always taken time isn’t fun. To tell them that they’re not always going to win isn’t fun. To tell them that even when they vote in every election, they’ll never elect a leader who delivers everything they want. Well, that’s just not inspiring. But it’s also true.
Nobody ever promised us these things. That’s democracy. But here’s the thing about democracy: we get to refresh it whenever we want. Older generations aren’t entitled to their full tenure. So, while I counsel patience and realism, I also fan the flames of their impatience and idealism. I tell them to join a campaign now, to start an advocacy group now, to run for office now. Stay at it not just until the people in power are more representative of what America actually is, but until they’re the ones in power themselves. Then make the system your own. Faster, smarter, more responsive to the needs of a modern, pluralistic democracy. And one way to do that is through my cardinal rule of speechwriting: help more leaders talk like actual human beings.
Robin Lindley: You also continue to work as a speechwriter and you note that you worked with President Obama after his tenure in office. Did you consult with the president on writing projects such as his monumental memoir Promised Land?
Cody Keenan: I worked for him full-time for four years after we left the White House, ultimately leaving after the 2020 election so that I could devote my time to writing Grace.
Robin Lindley: What sorts of clients do your work with as a speechwriter now?
Cody Keenan: All kinds. Progressive candidates, nonprofit, academic, and corporate. Our rule is that each client has to be putting more into the world – hopefully much more – than it’s taking out. But the best part of it is to be surrounded by a team of idealistic young speechwriters again. I missed that over the four years after the White House.
Robin Lindley: Would you consider working with a president at the White House again?
Cody Keenan: Maybe. Depends on who it is. For a speechwriter, it really, really depends on who it is. Speeches require a deeper relationship than a lot of other staff positions. But I’m also older and have a young daughter. Both of those things make the grind of the White House much less attractive.
Robin Lindley: It seems we’re more divided now than during the Obama years. I never thought I’d see Nazi rallies in America in the 21st century. Where do you find hope for our democracy at this fraught time?
Cody Keenan: My students. While politics as it is may make them cynical, they’re not cynical about America and its possibilities. Somehow, they’re not as plagued by fear or suspicion as older generations; they’re more tolerant of differences between race and culture and gender and orientation, not only comfortable navigating all these different worlds but impatient to make them all fairer, more inclusive, and just plain better. They’re consumed with the idea that they can change things. They just want to do it faster.
Robin Lindley: Is there anything you’d like to add for readers about your book or your work?
Cody Keenan: You’re going to love Grace. I wrote it because it’s a hell of a story and it’s the most intimate look at Obama’s approach to speechwriting that exists.
But I also wrote it, as I told Stephen Colbert when he had me on, to blow up people’s cynicism about our politics. Because politics isn’t some rigid system we’re trapped under. It’s us. It’s only as good as we are. That’s why I was so happy when Obama called it “an antidote to cynicism that will make you believe again.”
But I was just as happy to read a review that described it this way: “Grace is a refreshing departure from the flood of scandalous ‘literary’ flotsam that typically washes up in the wake of the transfer of power. This book might not make breaking-news headlines, but it just might restore a little faith in the presidency and the backstage men and women who work around the clock to fulfill the chief executive’s promises to the American people.” The publicist at the publishing house didn’t love the part about “breaking-news headlines,” because that’s what sells books – but I was proud to write it the way I did. There’s no sleazy tell-all in this book, but there are a bunch of great never-before-told stories about what it’s like to sit alone with Obama and unlock the right words for a fraught moment.
Robin Lindley: Thank you Cody for your generosity and thoughtful comments. Your book captures the reality of work in the tense and often exhilarating environment of the White House with a president who was devoted to creating a more just and tolerant nation. Best wishes on your continuing work and congratulations on Grace.Robin Lindley is a Seattle-based attorney, writer, illustrator, and features editor for the History News Network (historynewsnetwork.org). His work also has appeared in Writer’s Chronicle, Bill Moyers.com, Re-Markings, Salon.com, Crosscut, Documentary, ABA Journal, Huffington Post, and more. Most of his legal work has been in public service. He served as a staff attorney with the US House of Representatives Select Committee on Assassinations and investigated the death of Dr. Martin Luther King, Jr. His writing often focuses on the history of human rights, social justice, conflict, medicine, visual culture, and art. Robin’s email: email@example.com.