# The Longest American War You've Never Heard Of — and Why It Sounds Familiar

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Podcast: [Skipped History](https://stenobird.com/podcast/skipped-history-6825732)
Published: 2026-03-27T13:23:02+00:00
Episode link: https://skippedhistory.substack.com/p/the-longest-american-war-youve-never
Audio file: https://api.substack.com/feed/podcast/192306030/6ae67d1e750490f0b64a4f6e3095a7b5.mp3
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Duration seconds: 2181

## Resource

Today, Jamie Holmes explains how Andrew Jackson launched America’s longest war before Vietnam—with almost no understanding of what he was getting into. In The Free and the Dead: The Untold Story of the Black Seminole Chief, the Indigenous Rebel, and America’s Forgotten War , Holmes traces the Second Seminole War (1835-1842). Jackson invaded Florida knowing Black Seminoles were free and armed. When war broke out, he kept saying: why isn’t it over? What’s the problem? The war ended up costing up to $40 million (over $1 billion today), killing more soldiers from disease than combat, and could have been avoided entirely. Holmes sees a pattern echoing today: leaders imposing their will by force alone, denying realities they can’t defend on paper, while the media shapes our understanding of wars in real time. Jamie Holmes is a writer whose work has appeared in The New York Times , The New Yorker , The Atlantic , and elsewhere. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit skippedhistory.substack.com/subscribe

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