Progressive Era (1890-1913) Rough Riders on the attack, from Edison's "Infantry supported by Rough Riders at El Caney," 1899 MPEG Format (8.4 MB) Help With Video Credits 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. The U.S. was fighting against Spain over Spain's colonial policies with Cuba. Roosevelt recruited a diverse group of cowboys, miners, law enforcement officials, and Native Americans to join the Rough Riders. They participated in the capture of Kettle Hill, and then charged across a valley to assist in the seizure of San Juan Ridge, the highest point of which is San Juan Hill. page 1 of 2 Library Of Congress | Legal Notices | Privacy | Site Map | Contact Us VIDEO CREDIT: Edison Manufacturing Co. “U.S. Infantry supported by Rough Riders at El Caney / Thomas A. Edison, Inc. ; producer, James H. White,” 1899. Motion Picture, Broadcasting, and Recorded Sound Division, Library of Congress. Call Number FEC 2939.