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On This Day: Teddy Roosevelt’s Rough Riders Storm San Juan Hill, Cuba

Last updated: February 15, 2023

On July 1, 1898, Lt. Col. Theodore Roosevelt led his “Rough Riders” up the San Juan Heights against heavy artillery fire to help end the Spanish-American War.

The Battle of San Juan Hill

In the afternoon of July 1, 1898, in the midst of the Spanish-American War, American forces with orders to take Santiago, Cuba, found themselves in a difficult position. The U.S. forces were supposed to take El Carney and then San Juan Hill, but, according to, they were unable to secure El Carney, and as the troops advanced toward San Juan Hill enemy gunfire rained down upon them.

Richard Harding Davis, whose reporting of America’s Santiago campaign served to popularize the war, describes the Battle of San Juan Hill in detail. Excerpted from his 1905 “Notes of a War Correspondent,” Davis gives a firsthand account of the days leading up to the battle and the battle itself.

He notes that many troops stuck in the midst of gunfire were unable to advance until given futher orders, meanwhile they sat within close range of enemy guns and were killed and wounded as they waited. Retreat was difficult or impossible because of the narrow pathways they had used to advance.

Although Theodore Roosevelt and the Rough Riders are remembered in history as bravely pushing through and charging up Kettle Hill to secure it, PBS points out that Roosevelt was not alone in the Battle of San Juan Hill, and that Brig. Gen. Jacob Ford Kent, Gen. Samuel S. Sumner, John Coulter Bates and Gen.l Henry W. Lawton also played important roles in securing San Juan Hill and Kettle Hill.

A July 4, 1898, New York Times article analyzes the maneuvers and outcome of the July 1 battles for Santiago, and discusses the bravery of the soldiers “who never before had been in a general engagement where they had to face a furious artillery.”

This battle, the bloodiest of the Spanish-American War, caused the Spanish to try to leave Santiago Bay just days later, but U.S. forces destroyed all of their ships, according to the Library of Congress. The victory at the Battle of San Juan Hill led directly to the surrender of Santiago on July 17, a crucial victory preceding the end of hostilities in August. Furthermore, it launched the career of Theodore Roosevelt and popularized the Rough Riders.

Background: The Spanish-American War

The Spanish-American War was a result of Cuba’s struggle for independance from Spain, which had begun in 1885. Riots in Havana in 1898 prompted the United States to send the USS Maine into port, which was destroyed a month later, on Feb. 15, in a still-disputed explosion.

According to Encyclopedia Britannica, the United States demanded that the Spanish withdraw from Cuba, but instead Spain declared war on the United States on April 24, 1898. Fighting continued through August; the Treaty of Paris was signed on Dec. 10, 1898, and through it the United States gained control of Puerto Rico, the Philippines and Guam, and Cuba gained its independence.

Key Players: Theodore Roosevelt and the Rough Riders

Sources in This Story

  • This Day in History 1898: The Battle of San Juan Hill
  • PBS: Reporting America at War: Richard Harding Davis: The Battle of San Juan Hill
  • PBS: Crucible of Empire: The Spanish-American War Timeline
  • Library of Congress: Chronology of the Spanish-American War
  • The New York Times: Praising Our Fighters
  • Encyclopedia Britannica: Spanish-American War
  • findingDulcinea: Presidential Profiles: Theodore “Teddy” Roosevelt
  • The Theodore Roosevelt Association: Biography
  • The Spanish American War Centennial Website: A Brief History of the st United States Volunteer Cavalry (“Rough Riders”)

Theodore Roosevelt, born Aug. 27, 1858, was a man of many accomplishments. He helped to raise the 1st Volunteer Cavalry Regiment, of which he would be lieutenant colonel. The regiment, dubbed “The Rough Riders,” comprised an unusual mix of cowboys, Native Americans, friends from Manhattan, ranchers, African-Americans, speculators and Harvard classmates.

In Roosevelt’s bestselling 1899 book “The Rough Riders,” he writes in great detail about the group from its inception to the victorious return from Cuba, complete with exhaustive accounts of maneuvers and battles, day-to-day minutiae, and many descriptive passages about the individuals he chose to fight with.

In 1901, at age 42, he became the youngest president in history when he was sworn in after President William McKinley was assassinated. As president, Roosevelt is remembered for promoting conservation, placing the United States firmly in international affairs and starting construction of the Panama Canal, according to the Theodore Roosevelt Association. He is also famous for being a a big-game hunter, a hobby that inspired the stuffed animal that bears his name.

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