Teddy Roosevelt’s Rough Riders: The 1st US Volunteer Cavalry

The First US Volunteer Cavalry, nicknamed the Rough Riders, played a key role in one of the final battles of the Spanish-American War. As a great supporter of the war, Theodore Roosevelt felt inclined to create a volunteer cavalry. Roosevelt saw the opportunity that victory in the war would bring, as the US could become the primary power of the Western Hemisphere. The Rough Riders were applauded for their bravery as they charged up Kettle Hill and returned home as war heroes for their efforts. Teddy Roosevelt’s great leadership during the Battle of San Juan Hill was recognized by key political figures in the states, which helped jumpstart his notable political career.

When the US declared war on Spain in April 1898, Theodore Roosevelt abandoned his position as assistant secretary of the US Navy to set up a volunteer cavalry. Roosevelt recruited men of all types of backgrounds across the country to join the First US Volunteer Cavalry, popularly referred to as the Rough Riders. Roosevelt recruited Leonard Wood to become the colonel of the volunteer cavalry, while Roosevelt took the lieutenant colonel position. Roosevelt was a former New York National Guardsmen and had great leadership skills. He was excited at the opportunity to join the war, as he saw great potential in what the victory over the Spanish-American War could hold for the US and its position as a world power.

Once Roosevelt announced that he was establishing a volunteer cavalry, more than 20,000 applications to join the regiment poured in. Roosevelt even recruited some of his acquaintances and friends he had met previously through work and school. Among the men recruited were Native Americans, sheriffs and policemen, Texas Rangers, cowboys, and former ivy-league students and athletes.

The Rough Riders were one of the three volunteer cavalry regiments authorized by Congress. Recruits for the Rough Riders were mustered throughout the Midwest and West, including Native American territories, New Mexico, Arizona, and Oklahoma. Roosevelt was initially allowed to recruit 780 men, but it was later raised to 1,000 men. Roosevelt traveled to San Antonio, Texas, where more recruits were gathered and established a training base. The Rough Riders would spend a little over a month preparing for battle in San Antonio before departing to Tampa, Florida, where they would leave for Cuba.

Spain had established territories in Central and South America since colonial times. Spanish exploration of the Western Hemisphere began in the late 15th century. By the 19th century, Spanish possessions in Central and South America began to seek independence. Cuba had been fighting for its independence from Spain since 1868 when the Ten Years’ War began. The last war of liberation for Cuba was the Cuban War of Independence, which ended in 1898 upon the defeat of Spain in the Spanish-American War.

Political leaders in the Philippines followed suit as they made attempts to break away from Spanish rule in the 1890s. Puerto Rico sought independence from Spain between the 1880s and 1890s. The US already had interests in Cuba and other territories in Central America prior to the 1890s. Gaining control over these territories meant that the US would become a world power as it would have primary control over the Western Hemisphere. The US had invested tens of millions of dollars to acquire land in Cuba for American sugar interests, which helped fund Cuba’s revolutionary war efforts. However, President Grover Cleveland announced that the US would take a neutral position in the conflict between Cuba and Spain in June 1895.

In December 1896, President Cleveland reversed his decision to get involved in the war when Cuba was placed under martial law, and the people were moved under Spanish military jurisdiction in February 1896. President William McKinley took office in March 1897 during a time of restlessness and indecision on whether the US would intervene in the Cuban-Spanish conflict. On February 15, 1898, the battleship USS Maine exploded while anchored in Cuba’s Havana Harbor. At the time, it was almost certain that the explosion was caused by the Spanish. The USS Maine was sent to Cuba as a means of protection for US interests just a month prior to its explosion. The US Navy conducted an investigation of the explosion and determined that it was caused by a detonated mine located below the ship.

The explosion of the USS Maine directly led to US involvement in the war between Cuba and Spain and prompted the start of the Spanish-American War. Congress passed a joint resolution on April 20, 1898, which acknowledged Cuban independence and demanded Spain give up its possession of Cuba. This demand acted as an ultimatum. Upon Spain’s refusal to give up Cuba, any diplomatic ties between the US and Spain were severed. Just two days after the passing of the joint resolution and Spain’s rejection of the ultimatum, the US placed a naval blockade in Cuba and called for 125,000 military volunteers to prepare for war. The following day, Spain declared war on the US. Congress responded by voting to go to war with Spain on April 25.

Theodore Roosevelt and Leonard Wood had very little time to prepare their volunteer regiment, as the first battle in the war began on May 1, just six days after the war was declared. From the end of April to the end of May, Roosevelt and Wood recruited and trained the Rough Riders before they departed for Tampa to await further orders. Roosevelt described the men he recruited in his book entitled The Rough Riders, stating they all “possessed in common the traits of hardihood and a thirst for adventure.”

Commissioned officers attended officers’ school during training, while non-commissioned officers received similar schooling. The Rough Riders were trained in marching, skirmishing, and firing. Horses were purchased for the men, about half of which were unbroken. The Rough Riders were responsible for mastering the horses and then participated in horseback drills. Roosevelt noted that a great amount of training was accomplished within two to three weeks, and the men were taking to their duties and drills fairly quickly. They trained every day up until they received orders to transfer to Tampa. Their rifles, saddles, and other equipment didn’t arrive until just days before they received orders by wire to travel to Tampa by train on May 29.

Departing to Cuba

It took about four to five days for the men to arrive in Tampa. After all the training was done, some men were left disappointed as they were notified that four troops had to stay behind in Florida along with the horses. There were eight troops taken in total, each consisting of 70 men.

On June 7, Roosevelt received orders that they would depart from Port Tampa the following day to begin their expedition to Cuba.

The men sailed through the West Indies and past Guantanamo Bay before sighting the Santiago Harbor. On June 22, they received orders to make their landing at Port Daquirí in Santiago de Cuba. Prior to leaving for Cuba, the Rough Riders were paired with the First and Tenth Regular Cavalry. Altogether, they formed the Second Brigade led by Brigadier General S.B.M. Young. The horses the Rough Riders were authorized to bring to Cuba were thrown overboard to swim to shore. The regiment set up camp in a Cuban village called Siboney. They were scheduled to head toward Santiago at sunrise.

The Rough Riders had their first encounter with gunfire at the Battle of Las Guásimas. They also got to experience the hot and humid heat of the tropical climate. The Rough Riders trekked through thick jungle vegetation on a narrow trail. The Spaniards were set up at a junction of the trail and a valley road. The Rough Riders began their advance up a steep hill, battling with the intense heat. Some men didn’t make it along the way due to severe exhaustion and were left behind. At this point, there were less than 500 Rough Riders due to the loss of men up the hill and the others left behind at the shore to guard the baggage.

The regiment spent a little over an hour marching before they were halted. They had received word from Colonel Wood, who was ahead of the regiment, that they ran into a Spanish outpost. They filled their magazines and prepared for battle. The Rough Riders and the regular cavalries managed to push the Spaniards back and caused them to retreat from their position toward San Juan Hill. Victory in the Battle of Las Guásimas was important for the regiments to continue on their way to Santiago, located just downhill from where the Spaniards had set up their junction. The Rough Riders lost eight men in Las Guásimas, and the First and Tenth cavalries also lost eight men. A total of 52 men were wounded.

The Battle of San Juan Hill

The Battle of San Juan Hill caused the Rough Riders to earn their notoriety. Their advancement up Kettle Hill to the Spaniard’s San Juan fortification was one of the bloodiest battles in the war that led to US victory. On June 30, the Second Brigade received orders to ready themselves to march toward Santiago. The regular cavalry began their advancement before the Rough Riders. Lieutenant Colonel Dorst gave the Rough Riders orders to advance to support the regular cavalrymen.

On July 1, 1898, Theodore Roosevelt led his men in the charge up San Juan Hill. Bullets zipped by as Spanish guerillas were shooting down at them from perches. The Spaniards were using smokeless gunpowder, which made identifying their positions difficult. The Ninth and First Regiments joined the Rough Riders, with the Third, Sixth, and Tenth Regiments following closely behind. Approximately 490 men were involved in the charge up Kettle Hill, according to Roosevelt’s account in The Rough Riders. Although US regiments are believed to have suffered the most losses in this battle, they remained victorious. The regiments pushed the Spanish back, forcing them to retreat, and the US regiments raised the American Flag over San Juan Hill as a symbol of their victory.

After the Rough Riders and regular cavalry captured San Juan Hill, several more victories were achieved by Cuba and the US in the battles that followed. By July 3, the city of Santiago de Cuba was surrendered to American and Cuban forces. Peace negotiations began by the end of July 1898. In August, a cease-fire agreement was signed. On December 10, 1898, the Spanish-American War officially came to an end with the signing of the Treaty of Paris. The treaty established Cuba’s independence from Spain. It also forced Spain to surrender its possessions of Puerto Rico and Guam to the US. Spain sold their possession of the Philippines to the US for $20 million.

The Rough Riders returned home from the war in August 1898. Even before the Rough Riders entered the war, they received recognition from media outlets, such as The Sun and The Evening Star. Theodore Roosevelt received national attention for his efforts in leading the Rough Riders in the charge up Kettle Hill. He caught the eye of New York political leaders, specifically Thomas C. Platt.

Roosevelt was encouraged to run for the New York governor position under the Republican Party. He won the election and served as the governor of New York from January 1899 to December 1900. Platt quickly withdrew his support of Roosevelt as governor once he realized that Roosevelt was implementing policies he disagreed with. To prevent Roosevelt from tampering with New York’s corrupt political arena, Platt pushed him to run for vice president. Roosevelt was elected Vice President under President William McKinley, which led him to be sworn in as president following McKinley’s assassination in 1901.