The year is 1898 and the United States of America are at war with Spain. The Americans claimed they were upholding the Monroe Doctrine, which stated that the American people would not tolerate the continued influence of Old World imperialism in the New World. They were also retaliating for the sinking of the USS Maine, a ship anchored in Havana harbour, whose destruction had been blamed on the Spanish. The Spanish were defending Cuba, land they claimed as Spanish territory and had done so since the early 16th Century.

As the US army was small, President McKinley called upon volunteers to serve their country, creating the 1st United States Volunteer Cavalry, under the command of Colonel Leonard Wood.  The regiment was made up of men from Arizona, New Mexico, Oklahoma and Texas, as the men would be used to warmer climates. Wood’s second-in-command was a man called Theodore Roosevelt. Prior to the war, Roosevelt had been Assistant Secretary of the Navy and ten days after the sinking of the Maine, had been promoted to Acting Secretary of the Navy. Roosevelt would later resign in order to fight in the war he had advocated so strongly.

It turned out that Roosevelt would be invaluable to the regiment as he used his political connections to secure the regiment proper equipment, despite them only being a temporary volunteer force. By the time they were shipped out to Cuba, every soldier and NCO carried a Springfield Model Krag rifle while officers carried the newer M1895 Winchester. All men were also supplied with a Bowie hunting knife and a private donation had led to the acquisition of two tripod mounted Colt-Browning machine guns.

Teddy R

Las Guasimas

The regiment’s first taste of action came in late June after reconnaissance discovered a small Spanish outpost in the jungle. Despite the tactical advantage held by the Spanish as well as the constraints imposed by the thick jungle terrain, Wood and Roosevelt instructed their officers to act as spotters for their men, pinpointing enemy position and focusing fire on identified enemy positions.

The battle lasted approximately ninety minutes and ended with an American victory. While the Spanish had stopped the American advance, they had also been forced to withdraw from their outpost. Over the next six days, the regiment would rest at Las Guasimas and leave on June 30th with a new leader. During their time at the outpost, General Joseph Wheeler had fallen ill, leaving no-one in command on the field operations. Due to the chain of command, Colonel Wood was promoted to Brigadier General and put in charge of the cavalry. This left Roosevelt to take over command of the regiment. It would be from this point onwards that they would garner the nickname ‘Roosevelt’s Rough Riders’ or simple ‘The Rough Riders’.

San Juan Hill

A day after leaving the outpost at Las Guasimas, the Rough Riders marched eight miles closer to Santiago, the province capital. With no specific orders, Roosevelt’s cavalry regiment was to act as a distract for the thousand or so Spanish troops stationed at San Juan heights while an attack was launched against the Spanish stronghold of El Caney. However, this would prove to be the defining moment of the Rough Riders. As the battle began, Roosevelt and his men were caught at the bottom of Kettle Hill, exposed and vulnerable to the Spanish’s superior fire power. After some typical Roosevelting, orders were received for the Rough Riders to assault the hill and the regiment, along with a number of soldiers who had become isolated from their own units, began to climb the hill. Fearing that simply climbing the hill would lead to a massacre; Roosevelt gave the order to charge and set off on his horse, waving his hat. This bolstered the men on the hill and soon the Spanish were faced with a sea of Americans brazenly charging up the hill towards them. Kettle Hill was taken twenty minutes later and San Juan Hill fell within the subsequent hour.

Kettle Hill summit


The last major outing of the war for the Rough Riders was assisting in the siege of Santiago de Cuba, the province capital. While there was very little combat to speak of, the Rough Riders inspired the troops around them and their professionalism made them an essential part of the infantry blockade of the city. Surrender was finalised on July 16th.


After being shipped home, the Rough Riders celebrated in New York before being officially disbanded on September 15th. An annual reunion was held in Las Vegas, New Mexico between 1899 and 1967, when only one surviving veteran attended. That same veteran, Jesse Langdon, became the last survivor of the Rough Riders and died at the age of 94 in June of 1975.

Leonard Wood, the first commander of the Rough Riders, would go onto become the Army Chief of Staff in 1910. Theodore Roosevelt would go to be the Governor of New York, Vice-President and eventually President of the United States (1901-09).

There would be calls for the Rough Riders to be raised once again during the First World War. However, Roosevelt was unable to secure the support he had garnered during the Spanish-American War and the attempt was scrapped. While the Rough Riders were gone, their legacy would remain.



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