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America's longest war was against the American Indians (American Natives) which lasted from 1622 (Battle of the James River Settlement which had 347 colonists killed) to the Battle of Wounded Knee in 1890.

America's longest war against Another Country (Nation) was the Vietnam War. A war against the country of North Vietnam.

America's longest war and bloodiest war would be the Vietnam War with over 58,000 US Military men being killed there.

America's bloodiest war would be the American Civil War (US Civil War) with nearly a million dead, but Americans were killing Americans...thus the high number.

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Q: America's longest and deadliest war
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