“Jefferson deserved the musical more than Hamilton did.” — Walter Isaacson
Walter Isaacson has written the definitive biographies of Steve Jobs, Elon Musk, Albert Einstein, Benjamin Franklin, Leonardo da Vinci, and Jennifer Doudna. He spent years embedded with his subjects, and he has thought as hard as anyone about what makes a person bend the arc of history. His new book, The Greatest Sentence Ever Written, is a biography of a single line — the second sentence of the Declaration of Independence. He argues it was never meant to be a factual description of the country, but rather a promise it has spent 250 years trying to keep. In this conversation he makes a series of calls: that Jobs and Musk were both difficult men in roughly the same way, that empathy can be a form of vanity, that Benjamin Franklin’s two-word edit turned equality into a truth by definition, that we are surely getting things wrong today that our grandchildren will judge us for, and that the reporters who go out and gather the facts deserve to be paid by the machines that learn from them.
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This week the country turns 250, and I wanted to spend it with the person who wrote a whole book arguing that the most important thing America ever produced was this single sentence - “We hold these truths to be self-evident….”
Walter has spent his life writing about geniuses - Steve Jobs, Elon Musk, Jennifer Doudna, Ben Franklin, Albert Einstein - so we start there: how does parking an Airstream in someone’s driveway for two years change you, why a subject who’s a bit of a jerk is actually easier to write about honestly, and whether any of the geniuses he profiled would have gotten into Harvard. Then we get to the sentence itself, and to Ben Franklin quietly crossing out Jefferson’s “sacred” and writing in “self-evident.”
As a professor at Tulane, he tells his students to use AI, all of it, three models at once - but he draws a hard line at the writing itself. We close on Harvard’s part in the founding and on why getting worked up about your country is a form of loving it. I think you’ll enjoy this one.
As always, let me know what you thought: david@thecontextwindow.com
Happy birthday, America.
Chapters
[00:00] Cold open Isaacson’s blunt verdict on Steve Jobs and Elon Musk - and the Harvard word for it.
[00:08] Introduction Harvard, 1970. A kid from New Orleans who didn’t yet know that writing was a job.
[01:30] Two kinds of Louisianans Walker Percy told him the world already had too many preachers. Better to be a storyteller.
[02:35] How biography fell out of favor Doris Kearns Goodwin lost her tenure case for writing one, and for a while that left the whole field to outsiders.
[04:25] Fingerprints on history Kissinger taught that great forces drive history. Up close, beside Jobs and Musk, Isaacson saw individuals.
[06:40] Is empathy a weakness? Musk told him that empathy is sometimes just vanity. Isaacson thinks it’s why he failed running CNN.
[08:35] Two kinds of genius Jobs could read you and wound you on purpose. Musk, he says, is closer to a cyborg.
[10:20] Staying objective He liked Jennifer Doudna a little too much, and he knew it. Musk made objectivity easier.
[12:35] Would they have gotten into Harvard? Einstein was turned away by the Zurich Polytechnic. What does that say about how we choose?
[14:50] The greatest sentence ever written Why this one - and why a line that wasn’t true in 1776 may be the most important ever written.
[16:05] A forcing mechanism Lincoln, the suffragists at Seneca Falls, King, and Johnson all reached for the same sentence to pull the country closer to it.
[16:55] What are we getting wrong now? Fifty years from now, whose portrait comes down? Isaacson names fossil fuels, eating meat, and abortion, then turns to race.
[21:35] From sacred to self-evident Franklin crossed out “sacred” and wrote “self-evident.” A Scottish philosopher is the reason it matters.
[24:20] The pursuit of happiness Every earlier draft said “property.” Why Jefferson reached for happiness instead.
[26:35] The commons Boston Common was never just a park. The real question is what a society agrees to share.
[29:00] Out of balance? Is it the billionaires, or is it all of us? Michael Sandel’s “skyboxification,” and a harder look in the mirror.
[31:15] What would Franklin do? He could seat an abolitionist and a slaveholder under the same mulberry tree. He would not recognize our media.
[33:35] Why his students must use AI Use three different models, and show me every wrong turn. The finished paper is barely the point.
[35:00] Boswell & Company A biography startup named for Samuel Johnson’s biographer. The AI does the digging; the sentences are still typed by hand.
[37:20] Don’t eat the seed corn Somebody still has to sit in the trailer at Starbase and go to the Ole Miss game. Isaacson wants the AI companies to pay them for it.
[40:05] When intelligence is abundant We lived through this in the 1890s and built the high school. So what’s left for people once the machines are smart?
[43:40] The cradle of liberty Eight signers came out of Harvard, and Washington pitched his first camp in the Yard.
[45:15] Loving the country at 250 Is Harvard a force for good? And why, Isaacson says, the people most worked up about this country tend to be the ones who love it.
Guest bio
Walter Isaacson is the bestselling author of biographies of Steve Jobs, Elon Musk, Leonardo da Vinci, Benjamin Franklin, Albert Einstein, and Jennifer Doudna (The Code Breaker), as well as The Innovators. His latest book is The Greatest Sentence Ever Written (Simon & Schuster, 2025). He is the Leonard A. Lauder University Professor of History at Tulane University, and has been chairman and CEO of CNN, editor of Time, and for many years ran the Aspen Institute, the nonpartisan policy and leadership organization known for the Aspen Ideas Festival. A native of New Orleans, he came to Harvard in 1970, concentrated in History and Literature, wrote for the Lampoon, and served as president of the Signet Society. After graduating he studied at Oxford as a Rhodes Scholar. He teaches a course on the history of the digital revolution at Tulane and runs Boswell & Company, a startup he founded that produces commissioned biographies and memoirs for individuals, families, and companies, using AI alongside a team of his Tulane students.
Mentioned in this episode
Books
The Greatest Sentence Ever Written by Walter Isaacson
Steve Jobs by Walter Isaacson
Elon Musk by Walter Isaacson
The Code Breaker: Jennifer Doudna, Gene Editing, and the Future of the Human Race by Walter Isaacson
Benjamin Franklin: An American Life by Walter Isaacson
The Innovators by Walter Isaacson
Einstein: His Life and Universe by Walter Isaacson
The Tyranny of Merit by Michael J. Sandel - on meritocracy
What Money Can’t Buy by Michael J. Sandel - on the chipping away of the commons
Lyndon Johnson and the American Dream by Doris Kearns Goodwin - the biography that, Isaacson says, cost her tenure
The Life of Samuel Johnson by James Boswell - the namesake of Boswell & Company
People
Walker Percy - the novelist who told him to be a storyteller, not a preacher
Thomas Jefferson - author of the first draft (”sacred”)
Benjamin Franklin - who changed it to “self-evident,” and the hero of the new book
David Hume - Hume’s fork, the two kinds of truth
John Locke - the social contract and the proviso
John Rawls and Robert Nozick - his Harvard philosophy professors
Michael Sandel - the commons and the “skyboxification” of America
Drew Gilpin Faust - whose portrait comes down in a hundred years?
William R. Fitzsimmons - Harvard’s longtime dean of admissions, on looking for sparks
Henry Kissinger - great forces versus the difference people make
Albert Einstein - rejected twice by the Zurich Polytech
Bill Gates - processing power against Jobs’s “think different”
Abraham Lincoln and Theodore Parker - Gettysburg, and the arc of history that bends toward justice
Jennifer Doudna, Feng Zhang, and David Liu - the CRISPR race
James Boswell - the namesake of Boswell & Company
Also referenced: William Shakespeare (Henry V, Iago, Shylock), Plato, Henri Poincaré, Peter Galison, George Mason, Alexander Hamilton, E. B. White, David McCullough, Robert Caro, Jon Meacham, Kimbal Musk, Yo-Yo Ma
Ideas, concepts, and ventures
The Declaration of Independence and its second sentence
Hume’s fork - empirical truth (”London is bigger than Philadelphia”) versus self-evident truth (”all bachelors are unmarried”)
The social contract and the Lockean proviso - leaving “as good and enough” in common
Life, liberty, and the pursuit of happiness - and why it isn’t “property”
“Innovation is a team sport” - the myth of the lone genius in the garage
AI training data and who should be paid for the reporting underneath it
The 1890s knowledge economy, universal high school, and the land-grant colleges
Created by Humans - the marketplace for licensing creative work to AI, where Isaacson is an investor and advisor
Boswell & Company - Isaacson’s startup producing commissioned biographies with AI and a team of his Tulane students
Further reading and listening
Gettysburg Address, the Declaration of Sentiments (Seneca Falls), and Lyndon Johnson signing the Civil Rights Act - the later moments that, Isaacson argues, all reach back to the sentence
David’s companion solo episode, “Why new college grads can’t find jobs (it’s not AI)”, and his Forked Lightning essay on how remote work containerized the office
Peter Galison, Einstein’s Clocks, Poincaré’s Maps - on the mental leap behind relativity
“Our self-evident truths,” Harvard Gazette (November 2025) — Isaacson on the new book
Credits
Host: David Deming, Danoff Dean of Harvard College
Executive Producer: Denise Koller Consulting Producers: Tim Smith and Jonathan Palumbo Produced by: Hauser Studio, Harvard University - Anthony Di Bartolo and Adam Dusenberry; Cabin 3 Media - Justin Callahan, Editor
