Battle of San Juan Hill, the most significant U.S. land victory, and one of the final battles, of the Spanish-American War. It occurred on July 1, 1898. After the Battle of Las Guasimas in Cuba, Major General William Shafter planned to take Santiago de Cuba, the island’s second largest city. Reports of Spanish reinforcements en route to the city caused him to accelerate his plans. He ordered head-on assaults against three hilltop fortified positions that made up the city’s outer defenses.

　　24th U.S. Infantry during the Spanish-American WarThe 24th U.S. Infantry, made up of Black soldiers, during the Spanish-American War. (more)In Shafter’s plan, the 2d Division was to take El Caney, a village about 3.75 miles (6 km) east of Santiago, then swing south to join in a coordinated attack at 10:00 AM with the 1st Division, led by Brigadier General Jacob Kent, and the dismounted Cavalry Division, led by Brigadier General Samuel Sumner, against the two hills that sat on the San Juan ridgeline overlooking Santiago: San Juan Hill and Kettle Hill. Entrenchments, blockhouses, barbed wire, and several cannon protected the Spanish defenders on the hills, estimated at about 4,500 soldiers.

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　　Battle of San Juan Hill July 1, 1898 keyboard_arrow_right Shafter’s plan quickly fell apart. The march to attack positions was delayed, and unit deployment was confused by the narrow, crowded trail and enemy fire. At 8:00 AM, 1 July, artillery began firing on the Spanish positions, then ceased to avoid counterbattery fire. El Caney’s defenders, numbering no more than 500, put up fierce resistance against an attacking force that was ten times larger. Although it was well after noon before all the units were on line, the 2d Division was still heavily engaged at El Caney. Finally, at 1:00 PM, and under galling Spanish fire, an aide of Shafter’s gave approval to attack. The Cavalry Division’s two brigades, led by the 1st Volunteer Cavalry—the famed “Rough Riders,” heavily recruited from ranches and small towns in the American West and including a large number of Native Americans from what was then called the Indian Territory—under Colonel Theodore Roosevelt, charged and captured Kettle Hill, though suffering heavy casualties. Roosevelt himself was exposed to heavy enemy fire. “We had a bully fight,” said the future U.S. president, whose political career was greatly aided by his leadership this day. More than a century later, for his conspicuous valor in this battle, Roosevelt was posthumously awarded the Medal of Honor in 2001, more than a century after he was originally nominated for it.

　　Meanwhile, the Spanish on San Juan Hill tenaciously held back 1st Division’s infantrymen. Two American Gatling guns appeared, and their rapid volume of fire let the U.S. infantry renew their charge and break into the Spanish trenches. At the same time, cavalrymen attacked from Kettle Hill 500 yards (457 m) away, taking another section of San Juan Hill. By 2:00 PM, the last elements of Spanish resistance had been eliminated.

　　Participating in some of the heaviest fighting of this decisive American victory were the famed, all-black “Buffalo Soldiers,” one of whose officers was John “Black Jack” Pershing, soon to be commander of U.S. forces in World War I. The American force, augmented by Cuban rebels and numbering between 7,000 and 8,000 troops, was the most integrated of the 19th century, although it would be another half century before the U.S. military was officially desegregated. Of the Buffalo Soldiers, one Rough Rider remarked, “I never saw braver men anywhere.” Roosevelt himself praised them. saying, “no one can tell whether it was the Rough Riders or the men of the 9th [Cavalry] who came forward with the greater courage to offer their lives in the service of their country.” Five Buffalo Soldiers were awarded the Medal of Honor for courage under fire during the battle.

　　On July 3, a Spanish fleet in Santiago’s harbor was destroyed by a flotilla of U.S. warships. Two weeks later, on July 17, the Spanish formally surrendered Santiago.

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