#83 - Cody Keenan - Wonderful Struggle
Send us a text Meet Cody Keenan—best known as President Barack Obama’s longtime speechwriter and author of the bestseller "Grace." The conversation covers Cody’s career journey, from his early days working for Senator Ted Kennedy, to his rise as White House Chief Speechwriter, and beyond. Martin opens with humor and heartfelt admiration for Cody’s work, setting a warm, conversational tone. Additionally, the episode touches on the creative process behind presidential speechwriting: the i...
Meet Cody Keenan—best known as President Barack Obama’s longtime speechwriter and author of the bestseller "Grace."
The conversation covers Cody’s career journey, from his early days working for Senator Ted Kennedy, to his rise as White House Chief Speechwriter, and beyond. Martin opens with humor and heartfelt admiration for Cody’s work, setting a warm, conversational tone.
Additionally, the episode touches on the creative process behind presidential speechwriting: the intense collaboration, the immense pressure, and the quest for authenticity in political messaging. Cody reflects on some of the standout speeches he’s helped create, like the Selma anniversary address, and discusses the value of hope, optimism, and candor when writing for the public.
He also gives practical advice to aspiring speechwriters, stressing the importance of clear, conversational language and the dangers of becoming too lofty or detached from everyday people. Personal reflections, pop culture references, and “nerd outs” about superheroes give the episode an accessible, engaging feel.
Throughout, Cody and Martin discuss the importance of public service, the shifting nature of media and public discourse, and the power of storytelling to forge a common, uplifting narrative. They close with mutual appreciation and Cody’s advice to the next generation: be less cynical, invest in hope, and don’t be afraid to fail if you’re striving to make things better.
Overall, this episode balances behind-the-scenes political insight with relatable and inspiring life lessons, making it a compelling listen whether you’re a fan of politics, writing, or personal growth.
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Time Codes:
00:00 Cody's Notable Speeches and Appearances
05:10 Exclusive Interview Highlights
07:50 Oval Office Basement Stress Reflections
10:46 Legacy of War Silence
14:45 Meeting Presidents & Speechwriting Insights
15:41 Anonymity's Decline in Public Service
21:44 "Obama's Skill: Crafting Resonant Narratives"
23:53 Delayed Visit and Unifying Narratives
28:29 Envy of White House Advance Team
31:16 Visualizing Success Through Preparation
35:10 Moonshot Optimism
38:31 "Perseverance and Impactful Living"
39:11 "Milestone Gratitude Acknowledgment"
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00:00 - Cody's Notable Speeches and Appearances
05:10 - Exclusive Interview Highlights
07:50 - Oval Office Basement Stress Reflections
10:46 - Legacy of War Silence
14:45 - Meeting Presidents & Speechwriting Insights
21:44 - "Obama's Skill: Crafting Resonant Narratives"
23:53 - Delayed Visit and Unifying Narratives
28:29 - Envy of White House Advance Team
31:16 - Visualizing Success Through Preparation
35:10 - Moonshot Optimism
38:31 - "Perseverance and Impactful Living"
Cody Keenan, who wrote alongside President Barack Obama for 14 years, working his way up from deputy pirate to White House Chief Speechwriter and post-presidential collaborator.
In 2022, his first book, Grace, became an instant New York Times Bestseller in its own right. Cody was named the “Springsteen” of the Obama White House, even though he can’t play an instrument.
Obama calls him “Hemingway” for reasons that have little to do with his talent or seasonal beard (ask him sometime). And British GQ named Cody one of the 35 Coolest Men under 38 (and a Half), ahead of Ryan Gosling, but behind Tom Hardy (makes perfect sense).
He got his start in public service as a young aide to the legendary senator Edward M. Kennedy. He holds a master’s degree from Harvard University’s John F. Kennedy School of Government and a B.A. from Northwestern University.
Cody’s commencement addresses at NYU in 2015 and Northwestern in 2018 were highlighted as some of the year’s best, and in 2020, Northwestern’s graduating class of seniors chose him to deliver their “Last Lecture.”
He’s appeared on The Late Show with Stephen Colbert, TODAY, Morning Joe, Showtime’s The Circus, and is a frequent in-studio guest on Pod Save America and live television coverage of major presidential addresses.
Born in Wrigleyville, Cody finally got to write his dream speech just four days before Obama left office—one welcoming the World Champion Chicago Cubs to the White House.
To his wife Kristen’s enduring embarrassment, their White House courtship was documented on CNN. Today, they live in New York City with their young children Grace and Jack.
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Highlights from the Conversation:
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- Origin Stories: Cody’s birth literally sped up by a whole Geno’s East pizza, and why tavern-style is his go-to everyday slice.
- Honoring Service: The meaning behind his office décor—his grandfather’s WWII medals—and how personal legacy shapes public service.
- Speechwriting Secrets: What makes a truly great speech, the one Obama considers his best, and the importance of speaking like a real human (not just parroting lofty language).
- Favorite Speeches You Might’ve Missed: From touching eulogies to the oft-overlooked hour-long economic addresses, Cody shares the gems (and inside jokes) that didn’t make the headlines.
- Balancing Anonymity & Influence: Why speechwriters aim to remain invisible, but what it felt like when that veil was lifted.
- Music, Superheroes, and High School Regrets: Lauryn Hill on loop, what he’d say to his high school football team now, and the superhero speech he’d love to write.
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🎙️ Words of Wisdom Passed On:
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Cody’s top advice to the next generation? Set cynicism aside, be open to optimism, and keep fighting for the better—even if you fall flat nine times before succeeding the tenth. It’s a life well-lived.
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Time Codes:
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00:00 Cody's Notable Speeches and Appearances
05:10 Exclusive Interview Highlights
07:50 Oval Office Basement Stress Reflections
10:46 Legacy of War Silence
14:45 Meeting Presidents & Speechwriting Insights
15:41 Anonymity's Decline in Public Service
21:44 "Obama's Skill: Crafting Resonant Narratives"
23:53 Delayed Visit and Unifying Narratives
28:29 Envy of White House Advance Team
31:16 Visualizing Success Through Preparation
35:10 Moonshot Optimism
38:31 "Perseverance and Impactful Living"
39:11 "Milestone Gratitude Acknowledgment"
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🔥 Cody's Resources
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Website: https://fenwaystrategies.com/team/cody-keenan/
Book: GRACE - https://www.amazon.com/Grace-President-Obama-Battle-America/dp/0358651891
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Quotes:
And here we are, at the center of the arc, trapped in the gaudiest, most valuable, and most improbable water wheel the world has ever seen." - James Baldwin
“Everything now, we must assume, is in our hands; we have no right to assume otherwise." - James Baldwin
"Going straight is not the same thing as going forward." - Cody Keenan
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Keywords: Cody Keenan, speechwriting, Barack Obama, White House, President Obama speeches, Grace (the book), commencement addresses, Northwestern University, Harvard Kennedy School, public service, Selma speech, American history, Obama administration, military service, veterans, media coverage, optimism, cynicism, storytelling, Chicago Cubs, deep dish pizza, adversity, advance team, writing process, personal growth, team leadership, Jon Favreau, Jen Psaki, economic inequality, fictional speeches
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🎙️ Mentioned:
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President Obama
Michael Gerson
Jon Lovett
Pod Save America
Jon Favreau
Jen Psaki
