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T Roosevelt as a Rough Rider Research Paper

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Updated: Sep 3rd, 2019


Born in 1858, Theodore Roosevelt was the 26th President of the US but before his ascension to power, he served as a soldier in Cuba. He led a small regiment known as the Rough Riders during the Spanish American war in 1898. The Rough Riders was the first and only volunteer in United States Cavalry to fight during the Spanish American war and it was made up of volunteer soldiers who eventually fought on foot as infantry despite being a cavalry unit.

The civil war had weakened United States army and with the emergence of the Spanish American war, the then President William McKinley called upon 1,250 volunteers to lend a hand in Americas effort to dislodge Spain from the Caribbean and the Pacific.

Formation of the Rough Riders

Volunteers were mostly gathered from the South and South Western parts of the United States because the climate was hot and the four main collection zones were Arizona, New Mexico, Oklahoma, and Indian Territory (Miller, 1992). The reason for the selection of Southern men was due to the fact that the Southern climate was more similar to that of Cuba, the battle ground of the Spanish American war.

Due to the nature and circumstances that revolved around the amalgamation of the Rough Riders, the men in the Calvary were varied in terms of age and experience. Leonard Wood was appointed in the position of Colonel of The Rough Riders with Roosevelt serving as Lieutenant-Colonel and the unit was known as Wood’s Weary Walkers (Mathingham, 1998).

The men who volunteered to serve under these two men included gold and coal miners, civil war military veterans, hunters, police men, gamblers, cowboys, Buffalo soldiers, Native Americans Indians and college boys (Cannon, 2003). All the men were trained on how to use a gun and ride on horseback consequently fortifying the unit’s competence.

Lieutenant-Colonel Roosevelt was responsible for ensuring that the volunteer cavalry was adequately prepared and equipped similar to any other American military regiment. The volunteers were required to source for weapons before they went off to camp in San Antonio, Texas in May (Roosevelt, 1917).

The remainder of the equipment such as bullets, rifles, horse gear, canvas, uniform, tents among others was all procured by Lieutenant-Colonel Roosevelt. Roosevelt had an intention to turn the volunteer Calvary into a real military regiment and he made sure everything present within the U.S military was availed to the volunteers (Mathingham, 1998).

The Calvary’s uniform consisted of a droop hat, a blue beguile shirt, a pair of brown trousers, leggings, boots, and the soldiers also had a handkerchief which was supposed to be knotted around their necks. The uniform in particular is what earned them the name Rough Riders because they had the appearance of rough and worn out men who collectively looked like a cowboy cavalry.

Departure for war

After intense training which involved basic military drills, code of behavior, and habits involving conduct, compliance and etiquette, the men were finally ready for war. The training they had received was one of the best any Calvary could receive. Training was done on a daily basis and when the men had spatial constraints, they read books on tactic and used boards to perfect their skill (Miller, 1992). Theodore Roosevelt as a high ranking official was at most times immersed in the tactical study of war (Cannon, 2003).

He was a brilliant historian who knew how to identify the opponent’s behavior based on historical chronicles. On June 14, 1898, the regiment was brought together, addressed, motivated and shipped out to Cuba from Tampa, Florida (Roosevelt, 1917). Eight days later, the Rough Riders arrived in Daiquiri, Cuba on June 22, and two days later, they fought for the first time in Battle of Las Guasimas on June 24(Roosevelt, 1917).

Battle of Las Guasimas

Las Guasimas was a point of significance for the American troops because it was an advancement point for further military encroachment. The Americans had decided to attack in the early morning of June 24 when the Spaniards were still on their mark (Roosevelt, 1917). General Young led the offensive by the regulars through the jungle while Lieutenant-Colonel Roosevelt led the Rough Riders took a longer route that was supposed to lead to the open side of the Spaniards’ enclaves (Roosevelt, 1917).

Since many of his men had not received enough rest considering the rough riders had only arrived a day before, some of them fell out of formation or simply got left behind (Walker, 2008). The jungle they were fighting in was thick and foggy making it difficult to spot an enemy or a friendly regiment from more than twenty meters (Cannon, 2003).

Roosevelt managed to successfully navigate the less than five hundred Rough Riders that were still with him through the jungle and round the outpost. They effectively eliminated the opposition hiding in the entrenchments and brush consequently simplifying the advancement of the regulars. It was through the leadership of Lieutenant-Colonel Roosevelt that the battle of Las Guasimas was won after the Rough Riders eliminated the concealed opponent (Mathingham, 1998).

At the end of the two hour battle, the United States soon after took control of Las Guasimas, the Spanish outpost which stood along the road to Santiago. The American troops held position for six days allowing the Rough Riders time to eat, sleep, treat their wounds and bury the dead(Roosevelt, 1917). There was also a high occurrence of fever cases and many of the men became victim to the illness including General Joseph Wheeler.

Command of the Calvary was therefore left to Brigadier General Samuel Sumner and on the night of June 30 Colonel Leonard Wood was promoted in the field to Brigadier General, leaving Theodore Roosevelt as the bona fide Colonel of the Rough Riders and hence their name changed from Wood’s Weary Walkers to Roosevelt’s Rough Riders (Cannon, 2003).

Battle of San Juan Heights and Kettle Hill

On July 1, 1898 the Rough Riders now under Colonel Roosevelt were ordered to march along the road to Santiago to San Juan Heights where they were to reconnoiter and hold position. The role of the cavalry was basically to provide cover fire and distraction while artillery and battery were fired towards the Spaniards from afar (Miller, 1992). The Rough Riders were therefore not seen as important role players in this battle hence were given minor roles.

After American artillery fire was returned by the Spaniards, the Rough Riders found themselves in the midst of both friendly and enemy fire eventually taking cover along the riverbank and a nearby thicket to avoid shell fire (Roosevelt, 1917). Frustrated of waiting and afraid of being compromised, Colonel Roosevelt sent messengers to look for one of the generals and request for further orders to advance forward from their vulnerable position.

The Rough Riders were eventually ordered to help out the regulars in their assault on the hill’s façade and this time Roosevelt fought on horseback because he was now a Colonel and he needed the elevated height from the horse to help him recognized and supervise his men in battle (Walker, 2008).

Colonel Roosevelt observed that the American troops could not take the Kettle Hill because the loading and firing speed of the American rifles was slower. He suggested to one of the captains that the best option was to charge up the hill but his suggestion was declined (Mathingham, 1998).

Roosevelt later noticed the absence of the other Colonel and taking advantage, he stated he was in full control as the ranking officer and ordered a charge up Kettle Hill (Walker, 2008). Colonel Roosevelt rode off on his horse as the Rough Riders followed him with zeal and compliance up the hill (Roosevelt, 1917). The other soldiers from different units joined the uphill race and within twenty minutes Kettle Hill was captured (Roosevelt, 1917).

San Juan Heights which overlooked Santiago was captured an hour later leading to the surrender of the city of Santiago. The Spanish American war was finally over but the Rough Riders and the other troops were falling sick in large numbers. The Rough Riders were finally shipped home and taken to Montauk where they were quarantined till their release on September 16, 1898.


Theodore Roosevelt showed exceptional courage when he took over the leadership of the Rough Riders. The unit was essentially not a military unit rather a volunteer unit that devoted themselves to fight the Spanish American war. Rough Riders became widely celebrated after the war for their outstanding accomplishment and their 137 days service to the army.

The capture of Las Guasimas outpost was largely because of the tactical brilliance of Theodore Roosevelt. The capture of Kettle Hill can also be accredited to the bravery of Colonel Roosevelt who led the troops on an uphill frenzy to the top leading top the capture of San Juan Heights too.


Cannon, C. (2003). The Pursuit of Happiness in Times of War. Texas: Rowman & Littlefield.

Mathingham, P., H. (1998). T.R. takes charge: American History. New York: McMillan.

Miller, N. (1992). Theodore Roosevelt – A Life. New York: Quill/William Morrow.

Roosevelt, T. (1917). The Foes of Our Own Household. New York: George H. Doran Company.

Walker, D. (2008). From the San Juan Heights: Military History. New York: Campbell press.

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