On July 1, 1898, during the Spanish-American War, Colonel Theodore Roosevelt (1858–1919) led his American troops, known as the Rough Riders, on an attack of the Spanish blockhouse (a small fort) on San Juan Hill, near Santiago, Cuba. Newspaper reports made Roosevelt and the Rough Riders into celebrities, and even after he became a U.S. president, Teddy Roosevelt remarked that “San Juan was the great day of my life.”

San Juan Hill was part of a two-pronged assault on Santiago. While the Rough Riders regiment attacked the Spanish defenses at San Juan and Kettle Hills, another American division, led by General Henry Lawton (1843–1899), captured the Spanish fort at El Caney. The success of the two initiatives on July 1 combined to give the Americans command over the ridges surrounding Santiago. By July 3 the American forces had destroyed the Spanish fleet under the command of Admiral Pascual Cervera y Topete (1839–1909). On July 17 the Spanish surrendered the city.

Though the victory was critical to the outcome of the war, the assault on Kettle Hill and San Juan Hill had come at a high price: 1,600 American lives were lost, in a battle that had seen American troops—black and white—fight the Spanish shoulder to shoulder.