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

Podcast with Jamie Holmes

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.

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