The Battle of San Juan Hill occurred during the Spanish–American War, specifically on July 1, 1898, near Santiago de Cuba. The campaign aimed to capture Santiago, the main Spanish stronghold in Cuba, which had been fortified to resist American advances. American troops advanced with the aim of breaking through Spanish defenses on the hills surrounding the city. The battle was characterized by intense fighting and considerable casualties on both sides. Approximately 8,000 American troops faced around 7,000 Spanish soldiers, who were well-prepared and dug into their positions atop the hills.

The most famous unit involved was the Rough Riders, a volunteer cavalry regiment led by Theodore Roosevelt, who would later become the 26th President of the United States. Roosevelt's leadership and bravery during the charge on San Juan Hill significantly contributed to his public image and political career. The assault was marked by stark difficulties as troops faced heavy rifle and artillery fire. Despite the challenges, American soldiers scaled the hills, eventually capturing critical positions.

The victory at San Juan Hill proved pivotal, leading to the siege of Santiago and the eventual surrender of the Spanish forces. This battle not only showcased American military capability but also crystallized Roosevelt's reputation as a war hero. The aftermath influenced U.S. foreign policy and marked a significant moment in the emergence of the U.S. as a global power.