When the Spanish-American war broke out in 1898, Theodore Roosevelt left his post as Assistant Navy Secretary to form a cavalry called the Rough Riders: the rootin'est, tootin'est band of cowboys, college athletes, and Texas Rangers the U.S. has ever known. He took his boys to Cuba and led them to a victory at the Battle of San Juan Hill that won the war. He was even awarded a Medal of Honor for it posthumously in 2001.

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