The Battle of San Juan Hill During the Spanish-American War

Colonel Theodore Roosevelt and his Rough Riders, 1898

U.S. National Archives and Records Administration / Wikimedia Commons / Public Domain

The Battle of San Juan Hill was fought on July 1, 1898, during the Spanish-American War (1898). With the beginning of the conflict in April 1898, leaders in Washington, DC began planning for the invasion of Cuba. Moving forward later that spring, American forces landed in the southern part of the island near the city of Santiago de Cuba. Advancing west, plans were made for capturing the San Juan Heights which overlooked the city and harbor.

Moving forward on July 1, Major General William R. Shafter's men launched an assault on the heights. In heavy fighting, which included a charge by the famed 1st US Volunteer Cavalry (The Rough Riders), the position was taken. Consolidating around Santiago, Shafter and his Cuban allies commenced a siege of the city which ultimately fell on July 17.


After landing in late June at Daiquirí and Siboney, Shafter's US V Corps pushed west towards the port of Santiago de Cuba. After fighting an indecisive clash at Las Guasimas on June 24, Shafter prepared to assault the heights around the city. While 3,000-4,000 Cuban insurgents, under General Calixto García Iñiguez blocked the roads to the north and prevented the city from being reinforced, the Spanish commander, General Arsenio Linares, elected to spread his 10,429 men across Santiago's defenses rather than focus against the American threat.

The American Plan

Meeting with his division commanders, Shafter instructed Brigadier General Henry W. Lawton to take his 2nd Division north to capture the Spanish strong point at El Caney. Claiming that he could take the town in two hours, Shafter told him to do so then return south to join in the attack on the San Juan Heights. While Lawton was assaulting El Caney, Brigadier General Jacob Kent would advance towards the heights with the 1st Division, while Major General Joseph Wheeler's Cavalry Division would deploy to the right. Upon returning from El Caney, Lawton was to form on Wheeler's right and the entire line would attack.

As the operation moved forward, both Shafter and Wheeler fell ill. Unable to lead from the front, Shafter directed the operation from his headquarters via his aides and telegraph. Moving forward early on July 1, 1898, Lawton commenced his attack on El Caney around 7:00 AM. To the south, Shafter's aides established a command post atop El Pozo Hill and American artillery rolled into place. Below, the Cavalry Division, fighting dismounted due to a lack of horses, moved forward across the Aguadores River towards their jumping-off point. With Wheeler disabled, it was led by Brigadier General Samuel Sumner.

Armies & Commanders



  • General Arsenio Linares
  • 800 men, 5 guns


  • American - 1,240 (144 killed, 1,024 wounded, 72 missing)
  • Spanish - 482 (114 killed, 366 wounded, 2 captured)

Fighting Begins

Pushing forward, American troops experienced harassing fire from Spanish snipers and skirmishers. Around 10:00 AM, the guns on El Pozo opened fire on the San Juan Heights. Reaching the San Juan River, the cavalry waded across, turned right, and began forming their lines. Behind the cavalry, the Signal Corps launched a balloon that spotted another trail that could be used by Kent's infantry. While the bulk of Brigadier General Hamilton Hawkins' 1st Brigade had passed the new trail, Colonel Charles A. Wikoff's brigade was diverted to it.

Encountering Spanish snipers, Wikoff was mortally wounded. In short order, the next two officers in line to lead the brigade were lost and command devolved to Lieutenant Colonel Ezra P. Ewers. Arriving to support Kent, Ewers men fell into line, followed by Colonel E.P. Pearson's 2nd Brigade which took a position on the extreme left and also provided the reserve. For Hawkins, the objective of the assault was a blockhouse atop the heights, while the cavalry was to capture a lower rise, Kettle Hill, before attacking San Juan.


Though American forces were in a position to attack, the did not advance as Shafter was awaiting Lawton's return from El Caney. Suffering through intense tropical heat, the Americans were taking casualties from Spanish fire. As men were hit, parts of the San Juan River valley were dubbed "Hell's Pocket" and "Bloody Ford." Among those irritated by the inaction was Lieutenant Colonel Theodore Roosevelt, commanding the 1st US Volunteer Cavalry (The Rough Riders). After absorbing enemy fire for some time, Lieutenant Jules G. Ord of Hawkins' staff asked his commander for permission to lead the men forward.

The Americans Strike

After some discussion, a cautious Hawkins relented and Ord led the brigade into the attack supported by a battery of Gatling guns. Having been rallied to the field by the sound of the guns, Wheeler officially gave Kent the order to attack before returning to the cavalry and telling Sumner and his other brigade commander, Brigadier General Leonard Wood, to advance. Moving forward, Sumner's men formed the first line, while Wood's (including Roosevelt) comprised the second. Pushing forward, the lead cavalry units reached a road halfway up Kettle Hill and paused.

Pushing on, several officers, including Roosevelt called for a charge, surged forward, and overran the positions on Kettle Hill. Consolidating their position, the cavalry provided supporting fire to the infantry which was moving up the heights towards the blockhouse. Reaching the foot of the heights, Hawkins and Ewers' men discovered that the Spanish had erred and placed their trenches on the topographical rather than the military crest of the hill. As a result, they were unable to see or shoot at the attackers.

Taking San Juan Hill

Scrambling up the steep terrain, the infantry paused near the crest, before pouring over and driving out the Spanish. Leading the attack, Ord was killed as entered the trenches. Swarming around the blockhouse, American troops finally captured it after entering through the roof. Falling back the Spanish occupied a secondary line of trenches to the rear. Arriving on the field, Pearson's men moved forward and secured a small hill on the American left flank.

Atop Kettle Hill, Roosevelt attempted to lead an attack forward against San Juan but was followed by only five men. Returning to his lines, he met with Sumner and was given permission to take the men forward. Storming forward, the cavalrymen, including the African-American "Buffalo Soldiers" of the 9th and 10th Cavalry, broke through lines of barbed wire and cleared the heights to their front. Many sought to pursue the enemy to Santiago and had to be recalled. Commanding the extreme right of the American line, Roosevelt was soon reinforced by infantry and repulsed a half-hearted Spanish counterattack.


The storming of the San Juan Heights cost the Americans 144 killed and 1,024 wounded, while the Spanish, fighting on the defensive, lost only 114 dead, 366 wounded, and 2 captured. Concerned that the Spanish could shell the heights from the city, Shafter initially ordered Wheeler to fall back. Assessing the situation, Wheeler instead ordered the men to entrench and be prepared to hold the position against attack. The capture of the heights compelled the Spanish fleet in the harbor to attempt a breakout on July 3, which led to their defeat at the Battle of Santiago de Cuba. American and Cuban forces next began a siege of the city which finally fell on July 17 (Map).

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Hickman, Kennedy. "The Battle of San Juan Hill During the Spanish-American War." ThoughtCo, Jul. 31, 2021, Hickman, Kennedy. (2021, July 31). The Battle of San Juan Hill During the Spanish-American War. Retrieved from Hickman, Kennedy. "The Battle of San Juan Hill During the Spanish-American War." ThoughtCo. (accessed May 28, 2023).