The Rough Riders and the Battle of San Juan Hills

The Rough Riders

The Battle of San Juan Hills



  • The Rough Riders were led by future president Theodore Roosevelt. They were a rag-tag group of hunters, cowboys, polo players, sheriffs, glee-club singers, Native Americans, and athletic college buddies. But the group was key to winning two important battles against the Spanish in Cuba. The first of these victories was at the Battle of Las Guasimas on June 24, 1898. During the fighting, dozens of the Rough Riders were hurt or worse, but they managed to drive the Spanish away. After Wood and some of the Rough Riders flanked the Spanish army and forced them to withdraw, the American army prepared for an assault on the city of Santiago.
  • Roosevelt’s superior officer was promoted on the battlefield and sent to another unit. This left the Rough Riders entirely in Roosevelt’s hands. After the victory at Los Guasimas, the Rough Riders started to lay the groundwork to capture the city of Santiago, which was a major city in Cuba. Taking the city was key to freeing the island from Spanish rule. The Spanish had retreated to defend the San Juan Heights from the Americans.
  • A week later, on July 1, 1898, an American force, which outnumbered the Spanish 16-to-one, bravely charged the hill to attack the Spanish. The Spanish were dug into the hill and had clear sight of the American forces as they climbed the hill, making them easy to shoot. The bottom of the hill, under constant fire from the Spanish, was called ‘Hell’s Pocket’ and many brave American troops lost their lives here. As well as being shot, casualties also resulted from heat exhaustion. Despite their losses, the American troops continued to advance towards the Spanish at the top of the hill.
  • The American forces made excellent use of a new type of gun – a machine gun called a Gatling that could fire bullets very quickly. Machine guns were normally used to defend positions, but the Americans very cleverly used their Gatlings in attack, moving the guns forward, rather than having them in the same position. These guns were not only important in returning fire to the Spanish, but the sound of the guns inspired the American troops to advance, even when they were easy targets for the Spanish. The Americans suffered many casualties, but were able to take the hill from the Spanish.
  • Roosevelt led a series of charges up a place called Kettle Hill to get to the San Juan Heights. Although Teddy and his men were off their horses and facing enemy gunfire, they bravely rallied and charged the hill. Other regiments continued alongside the Rough Riders, and the American flag was raised over the San Juan Heights shortly thereafter. This critical victory became known as the Battle of San Juan Hill. It cemented Roosevelt’s reputation as a war hero and decided the outcome of the Spanish-American War.
  • The Americans also defeated the Spanish at the Battle of El Caney on the same day. Soon after, the U.S. Navy defeated the Spanish Royal Navy at the Battle of Santiago de Cuba, effectively ending the Spanish-American War, leading to the Spanish asking for peace and the United States taking Cuba, Puerto Rico, Guam, and the Philippine islands from Spain.