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Thomas Jefferson knew slavery was wrong — he wrote a blistering condemnation of it in the original Declaration draft that was removed by southerners — yet he chose to maintain it at Monticello, making him both an incomparable genius and a terrible hypocrite, and Americans must hold both truths simultaneously.

Conan highlights the central Jefferson paradox: he knew better than anyone that slavery was wrong (proven by his original Declaration draft), but he loved Monticello and could only sustain it through slavery. Conan argues we must honor his gifts as a writer and thinker while honestly confronting his moral failure. ✦ AI generated

Conan O'Brien · The Rest Is History · 2026-07-25 · original ↗

starts at this moment · 26:22

The greatest fact that you guys brought up in the Jefferson episode was there are probably a lot of people who would guess that, well, this is the world that Jefferson was brought up in. He's a Virginian. Slavery is just part of their world. And he didn't know any better. And that's just not true. He wrote in his original draft of the Declaration of Independence, he lambasted slavery and tore away at it and said this is a great evil and that other southerners made him take it out. But he knew better. He knew better. And as you pointed out, if you've been to Monticello, it's absolutely stunning. He's very proud of Monticello. And he probably as you said probably loves Monticello more than anybody or anything and the only way he can keep it going is with slavery. So, it's a terrible failing and I'm a big believer in we need to acknowledge those things while not throwing the baby out with bath water and closing one's eyes to the fact that he was a remarkable writer, a remarkable ideologue, a remarkable politician, a remarkable president. It's a question for Americans that I am not qualified to opine on. How easy it is to do that — to have this man of incomparable genius who also has this great kind of moral blot and can the two be squared.

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26:04fault, but I think he would have missed the appointment. Um because he had business to conduct, but he would have sent someone who would have um I think probably kicked Hamilton to death before pistols were even chosen. [laughter] Some some MFA fighter. I I think you're you're probably right with that. And of course, Hamilton's I mean, we talked about Burr, but Hamilton's great opponent is Jefferson, who was the last

26:30of the founding fathers that we did. And I think by miles the most remarkable, extraordinary genius and extraordinary hypocrite. And the challenge really of making sense of the American Revolution is the challenge of making sense of Jefferson. The greatest fact that you guys brought up, I thought, in the Jefferson episode, was there are probably a lot of people who would guess that, well, this is the world that Jefferson

27:02was brought up in. He's a Virginia. Um, slavery is just part of their world. Uh, and he didn't know any better. And that's just not true. and that you said that, you know, he he wrote in his original draft of the Declaration of Independence, uh, he lambasted slavery and tore away at it and said this is a great evil and that, uh, other southerners made him take it out. But he

27:31knew better. He knew better. And as you pointed out, he, if you've been to Montichello, it's absolutely stunning. He's very proud of Montichello. and he probably as you said probably loves Montichello more than anybody or anything and the only way he can keep it going is you know with slavery. So, it's a terrible failing and I'm a big believer in we need to acknowledge those things while I think not throwing the baby out

28:01with bath water and closing one's eyes to the fact that he was a remarkable writer, a remarkable ideologue, a remarkable politician, a remarkable president. And I suppose it's a it's a question for Americans that I am not qualified to appine on. How easy it is to do that to have this man of incomparable genius who also has this great kind of moral blot and can the two be squared. You and

28:32Dominic do this all the time on your podcast. You'll be talking about um you know Admiral Lord Nelson and you absolutely I mean uh Dominic clearly has a portrait of Nelson in his bedroom that he that he looks at just before he he pulls up the covers. You know he gave me um a letter of Nelson. >> Oh. And it's got a little picture of Nelson. So actually it's in my bedroom.

28:55So >> Oh, okay. So you're just as guilty but you know a a good Englishman loves Lord Nelson. And then there are times where he really lets you down. Um, and you think he behaved very poorly and showed bad character with his with his wife. And we all have to do that all the time. We all have to square the remarkable thing about these people and the

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