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
Battle of Santiago de Cuba only a few inconclusive skirmishes resulting. For his part, Cervera was content to wait, hoping for bad weather to scatter the Americans so that he could make a run to a position more favorable for engaging the enemy. However, U.S. land forces began to drive on Santiago de Cuba, and by the end of June 1898, Cervera found himself unable to remain safely in the harbor, and Governor-General Blanco y Erenas wanted a sortie, stating, "it is better for the honor of our arms that the squadron perish in battle ...". The breakout was planned for 09:00 on Sunday, July