In May 1898, one month after the outbreak of the Spanish-American War, a Spanish fleet docked in the Santiago de Cuba harbor after racing across the Atlantic from Spain. A superior U.S. naval force arrived soon after and blockaded the harbor entrance. In June, the U.S. Army Fifth Corps landed on Cuba with the aim of marching to Santiago and launching a coordinated land and sea assault on the Spanish stronghold. Included among the U.S. ground troops were the Theodore Roosevelt-led “Rough Riders,” a collection of Western cowboys and Eastern blue bloods officially known as the First U.S. Voluntary Cavalry.
The U.S. Army Fifth Corps fought its way to Santiago’s outer defenses, and on July 1 U.S. General William Shafter ordered an attack on the village of El Caney and San Juan Hill. Shafter hoped to capture El Caney before besieging the fortified heights of San Juan Hill, but the 500 Spanish defenders of the village put up a fierce resistance and held off 10 times their number for most of the day. Although El Caney was not secure, some 8,000 Americans pressed forward toward San Juan Hill.
Hundreds fell under Spanish gunfire before reaching the base of the heights, where the force split up into two flanks to take San Juan Hill and Kettle Hill. The Rough Riders were among the troops in the right flank attacking Kettle Hill. When the order was given by Lieutenant John Miley that “the heights must be taken at all hazards,” the Rough Riders, who had been forced to leave their horses behind because of transportation difficulties, led the charge up the hills. The Rough Riders and the black soldiers of the 9th and 10th Cavalry regiments were the first up Kettle Hill, and San Juan Hill was taken soon after. From the crest, the Americans found themselves overlooking Santiago, and the next day they began a siege of the city.
On July 3, the Spanish fleet was destroyed off Santiago by U.S. warships under Admiral William Sampson, and on July 17 the Spanish surrendered the city–and thus Cuba–to the Americans.