The Rough Riders was a nickname given to the 1st United States Volunteer Cavalry, one of three such regiments raised in 1898 for the Spanish–American War and the only one to see combat. The United States Army was small, understaffed, and disorganized in comparison to its status during the American Civil War roughly thirty years prior. Following the sinking of USS Maine, President William McKinley needed to muster a strong ground force swiftly, which he did by calling for 125,000 volunteers to assist in the war. The U.S. had gone to war in opposition to Spanish colonial policies in Cuba, which was then torn by a rebellion. The regiment was also nicknamed "Wood's Weary Walkers" for its first commander, Colonel Leonard Wood. This reflected their dissatisfaction that despite being cavalry, they ended up fighting in Cuba as infantry, since their horses were not sent there with them.

The Spanish–American War began in the aftermath of the internal explosion of USS Maine in Havana Harbor in Cuba, leading to United States intervention in the Cuban War of Independence. The war led to the United States emerging predominant in the Caribbean region, and resulted in U.S. acquisition of Puerto Rico, Guam, and the Philippines. It also led to United States involvement in the Philippine Revolution and later to the Philippine–American War.