The Rough Riders

The Rough Riders

The Spanish-American War


After declaring war, the United States Navy began a blockade of Cuba so that Spain could not resupply its forces. The Americans were also aware of a fleet of Spanish ships anchored in Manila Bay in the Philippine Islands. The U.S. Navy sank all of the Spanish ships without any loss of their own. The war was underway.

Rather than stay in the comfort of his government office, Teddy Roosevelt resigned his post and formed the 1st U.S. Volunteer Cavalry to help fight the war. Alongside his friend Leonard Wood, an American war hero, Teddy sifted through nearly 25,000 applications to create the group that came to be known as the ‘Rough Riders.’

The Rough Riders

Ultimately, the Rough Riders was 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 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. 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 attach, moving the guns forward, rather than having them in the same position
  • 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.
  • 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.