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American History

The Bold Life of the Hero of San Juan Hill

William McKinley - Theodore Roosevelt
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13. Roosevelt assumed command of the Rough Riders while in Cuba

Roosevelt (far right) stands to the left of his commanding officer in Cuba, Colonel Leonard Wood, US Army. Wikimedia

The overall commander of the American cavalry in Cuba was Joseph Wheeler, a veteran of the Confederate Army during the Civil War. When he became ill, a shuffling of the senior officers put Wood in command of a brigade, and Roosevelt became a colonel of volunteers and in command of the Rough Riders, who by then were calling themselves “Wood’s Weary Walkers”. After a week of being encamped at Las Guasimas, the regiment was ordered to move forward a distance of about eight miles, near the San Juan heights, and remain in position there until they received further orders.

The Rough Riders moved forward with the rest of the American dismounted cavalry on July 1, 1898. They were to join in an attack which threatened the Spanish-held city of Santiago de Cuba, by taking the heights which overlooked the city. The names of San Juan Hill and nearby Kettle Hill were given to positions occupied by entrenched Spanish troops by the Americans. As the battle opened the Rough Riders had no orders to advance, but they came under artillery fire and Roosevelt, one of the few men on the battlefield who was mounted, sent messengers urging that he be allowed to move his regiment forward in support of the infantry preparing to assault Kettle Hill.

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