History Impossible

The Slave Who Would Be a Spy (w/ Isaac Willour)

History Impossible

Show Notes

Slavery is often known as the United States’ original sin, and for good reason. Much of our perceptions of it are informed both by the Civil War’s cause and outcome, and the contradictions—and even moral hypocrisy—that it created with our Founding Fathers’ professed beliefs. Contradiction is the theme not just of the United States’ values and history, but it also a major theme of this episode of the podcast.

In this newest installment of History Impossible, we’re looking at the extraordinary life of James Armistead Lafayette, the slave who would become the Colonies’ most vital spy during the Revolutionary War. I had never heard of this man before, but after reading fellow Keinrath Publishing writer Isaac Willour’s stirring and powerful portrait of the man—which everyone should check out here—I felt that it would be fitting for me and Isaac to chat about it. This conversation was the result of that, in which we discuss the circumstances of Armistead Lafayette’s life defined by action as well as the seemingly baffling contradiction that he shared with the Founding Fathers themselves: his owning of slaves after his own manumission.

Isaac’s writing has appeared not just in Keinrath, but also publications including National Review, The Daily Wire, and the American Institute for Economic Research. He has also appeared in the New York Times and the Wall Street Journal. Amid all of that, though, he has managed to carve out time to be fascinated in history and that led us to chatting about this story. It is a fascinating tale, and I hope you all enjoy.

…

History Impossible has been made possible by the following generous supporters on Patreon, Substack, and PayPal. Please consider donating today to help keep me free and this show alive:

David Adamcik David Alsbach Rajan Athul Robert Babeon Michael Beach Benjamin Greg Bosai Johannes Breitsameter Carol ABC Charles C Curtis Christiansen Clayton Connell Cliffydeuce CR B.Cyr daddygorgon Danny Lynda Davis Paul DeCoster Regina Dick-Endrizzi Neil Dickens Nathan Diehl Bob Downing Dramicas Martin E. Gavin Edwards Howie Feltersnatch Pierre Ghazarian Jayson Griesmeyer Nathan Grote Benjamin Hamilton Peter Hauck Henry Eric Hodges Carey Hurst Mike Jarulic Joe6245 Russell Johnson Lionel Joseph Thomas Justesen Mike Kalnins Bryn Kaufman Leah Kodner Benjamin Lee Constance Loucks Maddy Mounty of Madness Jose Martinez Mike Mayleben Judy McCoid Kyle Mohney Kostas Moros Ryan Mortenson Cameron Needham Skip Pacheco Mel Padden David Page Molly Pan Jeff Parrent Sr. Powell Brian Pritzl AnaR737 PJ Rader Gleb Radutsky Aleksandr Rakitin Reptilycus Matthew M. Rice Phillip Rice Terry Rosen Chris Rowe Dan S Jon Andre Saether Jake Scalia Emily Schmidt Julian Schmidt Andrew Seeber Joshua Simpson Cameron Smith Jerry Spangler timetosuccedd1995 Thomas Squeo Athal Krishna Sundarrajan Jared Cole Temple Ward Van Roy Pierre Vorupuni Robert VS Jonny Wilkie Michael Wroblewski F. You Greg Zink

Become a supporter of this podcast: https://www.spreaker.com/podcast/history-impossible--5634566/support.

More from History Impossible

Sep 30, 2026

Hey everyone. No preamble here. Just a nice bonus as a thank you for your continued support. As the title suggests, this is an audio adaptation of an essay I wrote about the 25th anniversary of 9/11 and how it led me to reflect on my generation, that is millennials, seems to believe about itself regarding trauma, adversity, and the future.

Sep 22, 2026

We often hear about how the Second World War was more morally nuanced and complex than we have been led to believe. This is, to a certain extent, very true. The Axis powers meted out a level of genocidal destruction and suffering upon tens of millions of people across the world, decimating generations in places as far flung as Poland and the Philippines, and Croatia and China. To call their actions existential by their very nature is to arguably undersell the threat they posed. The Allies realized these were the stakes and were eventually faced with a very real question: what would it take to stop such a threat? It required what many have come to believe was the unthinkable: meeting destruction with destruction. And in meeting the Axis violence with more violence did indeed bring the war to its ultimate end.

Sep 7, 2026

In this newest episode of History Impossible we’re joined a second time by Richard Lim, host of the This American President podcast, who last appeared on this program a couple years ago to discuss the insane, contentious election of 1876. He is also the author of a new book, Refusing a Crown: How George Washington Changed the World, which releases on October 13, 2026, and covers the most significant aspect of America’s first president: his restraint from seizing power that almost certainly would have remained his.

Aug 18, 2026

“Because remember: Russia is a religious experience.” Those are the oft-repeated and well-said words by the host of The Eastern Border podcast, my good friend Kristaps Andrejsons. They are well-said because there are very few alternatives for explaining Russian actions, rhetoric, and political culture over the past near half-decade in its World War I-style conflict with Ukraine. The Russian religious experience, made emblematic by Kristaps’ and my favorite shared punching bag Aleksandr Dugin, is a phenomenon best understood as a more formalized and colossal version of what ISIS was ten years ago, and it helps explain why Kristaps believes the spiral of the Russian state as we currently know it is beginning in 2026.

Aug 11, 2026

Antizionism, as it has become, has been having a bit of a moment for going on three years. It is a tough nut to crack, given its various claims of varying legitimacy and, as we have covered more than once on History Impossible, its increasing tendency to veer into outright antisemitism, especially by those looking for a supposedly intellectual and moral veneer for their racial and geopolitical fixations. Part of the reason for this confusion is the complex intellectual history of the position, which, after 1948, became more complicated than the relatively straightforward debate over Jewish statehood before, during, and after the Holocaust.

See all episodes →