History Impossible14 Maalis 2025

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

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.

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