Teddy roosevelt and the rough riders july 1 1898 before becoming president of the united states theodore roosevelt was the assistant secretary of the navy he resigned in 1898 to organize the rough riders the first voluntary cavalry in the spanish american war. Among theodore roosevelts many lifetime accomplishments few capture the imagination as easily as his military service as a rough rider during the spanish american war america had become interested in cubas liberation in the 1890s as publications portrayed the evil of spanish rule no one . Original title colonel roosevelt and his rough riders at the top of the hill which they captured battle of san juan hill us army victors on kettle hill about 3 july 1898 after the battle of san juan hills left to right are 3rd us cavalry 1st volunteer cavalry with roosevelt at center and 10th us cavalry. Rough riders the most famous of all the units fighting in cuba the rough riders was the name given to the first us volunteer cavalry under the leadership of theodore rooseveltroosevelt resigned his position as assistant secretary of the navy in may 1898 to join the volunteer cavalry
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