Teddy Roosevelt's Rough Riders: Definition & San Juan Hill

Instructor: Katie Cote

Katie teaches high school social studies and has a master's degree in history from Providence College.

The Rough Riders were a diverse group of volunteer cavalry soldiers who served during the Spanish-American War in 1898. The men were led by the tireless Teddy Roosevelt (1858-1919) and are best known for their overwhelming victory at San Juan Hill in Cuba.


When the United States found itself at war with Spain in April of 1898, Teddy Roosevelt quit his position as Assistant Secretary of the Navy to serve as lieutenant colonel under Leonard Wood. The men worked together to form a regiment of cavalry volunteers. The unit would become one of the most famous regiments in American history. So, what did this group do to earn such a prominent place in history books?

Roosevelt posing in his Rough Riders uniform
Teddy Roosevelt posing in his Rough Riders uniform

Who Volunteered?

The volunteers were mostly recruited from the southwestern states of Arizona, New Mexico, Oklahoma, and Texas. Here, the heat and terrain were similar to that of Cuba, making the transition to life on the island of Cuba that much more smooth for the troops.

The unit was a unique mixture of men from a variety of ethnic and socioeconomic backgrounds, including, but not limited to: cowboys, ranchers, miners, and hunters as well as Ivy League graduates, polo players, and yachtsmen. All men were physically strong as well as experienced on horseback. They were both well-trained and well-equipped, and this ensured the troops would see combat (this was often not the case with volunteer units).

The men trained at Fort Sam Houston in San Antonio, Texas. At the end of May, after training for barely a month, the Rough Riders traveled to Tampa, Florida, where they would board a ship that would take them to war in Cuba.

Rough Riders in Cuba

In late June, as Roosevelt and his Rough Riders made their way towards Santiago, the soldiers stumbled into battle when the Spanish attacked the men without warning. The battle occurred at Las Guasimas, an inland town known to hold large numbers of Spaniards. Although the battle was short, the Spanish fought with intensity, killing and injuring dozens of American troops within minutes. This confrontation gave the men a taste of what was to come the following week at San Juan Hill.

July 1, 1898 marked the day that US troops attacked Spanish forces at Santiago. The goal was to charge up the Kettle and San Juan Hills. From this position, the troops could fire down on Spanish troops from a superior vantage point. However, due to some confusion when troops were leaving Tampa for Cuba, the horses were not shipped, so the Rough Riders were forced to attack the Spanish on foot while facing heavy fire. The Rough Riders marched on Kettle Hill and then moved on to take San Juan Hill.

The Rough Riders pose victoriously on top of San Juan Hill (Roosevelt is in the center)
Teddy Roosevelt and his Rough Riders

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