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.










