Battle of San Juan Hill Battle of San Juan Hill The Battle of San Juan Hill (July 1, 1898), also known as the battle for the San Juan Heights, was a decisive battle of the Spanish–American War. The San Juan heights was a north-south running elevation about east of Santiago de Cuba, Cuba. The names San Juan Hill and Kettle Hill were given to the location by the Americans. This fight for the heights was the bloodiest and most famous battle of the war. It was also the location of the so called "greatest victory" for the Rough Riders, as stated by the press and
Siege of Santiago along San Juan Heights. In the charge at the Battle of San Juan Hill U.S. forces captured the Spanish position. At the Battle of El Caney the same day, U.S. forces took the fortified Spanish position and were then able to extend the U.S. flank on San Juan Hill. The destruction of the Spanish fleet at the Battle of Santiago de Cuba allowed U.S. forces to safely besiege the city. On July 3, 1898, the same day as the naval battle, Major General William "Pecos Bill" Shafter began the siege of Santiago. Shafter fortified his position on San Juan Heights.