An antique American photograph of a standing Rough Rider. Matted and framed. The most famous of all the units fighting in Cuba, the Rough Riders was the name given to the First U.S. Volunteer Cavalry under the leadership of Theodore Roosevelt. The Rough Riders were in Cuba from June 22, 1898, until early August 1898, during the Spanish-American War. Collectible Americana, Historical Relics.