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Samuel Feygin

Professor Vincent DiGirolamo

History 1000

4 April 2019

Theodore Roosevelt: American Perseverance

Theodore Roosevelt, the 26th President of the United States, was born on October 27,

1858 in New York City, New York. His rise to the Presidency is a tale worth telling and arguably

might have never happened if not for the Spanish-Cuban-American War and his involvement in

it. He told the story of his adventures in Cuba in his autobiography, titled The Rough Riders,

which was published in 1899. While Roosevelt made sure to include plenty of details of his

wartime experiences, there were many prior influences that made him the man he was in Cuba

that initially need to be brought into the forefront for perspective purposes. With his upbringing

in mind, Roosevelt overcame so much to become a true American Hero and made sure to

document the experiences that ultimately contributed towards the legacy he is known for today.

Growing up, Theodore Roosevelt suffered from severe asthma, but where many people

would have given up, Roosevelt refused to. He took up weight lifting, running, horseback riding,

and boxing, and managed to become a very good athlete. Although born into wealth, Roosevelt

experienced many rough periods in his life. Yet nothing could have possibly prepared him for

what happened in 1884 when his mother and first wife died on the same day. Roosevelt was

shattered, and the tragedies nearly ended his political career. Roosevelt took a brief leave and

went to the Dakotas where he worked on a ranch for several years. While there, he became an

avid hunter and outdoorsman. Afterwards, he returned to New York in the 1890’s where he rode

a rapid ascension through politics to serve as assistant secretary of the US Navy. With war
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breaking out with Spain, Roosevelt was eager to join the fight and left the Navy Department to

raise a group of volunteers to fight the Spanish in Cuba. The unit was made up mostly of wealthy

Easterners and Western cowboys from the Arizona and New Mexico territories. The Unit

became known as the Rough Riders and they gained national fame for their roles in capturing

Santiago and Kettle Hills during the conflict. Media coverage of Roosevelt’s personality and the

exploits of his men catapulted the 39-year old Roosevelt into the national spotlight. Roosevelt

would then pen his renowned autobiography and would ride his newfound fame into the

governorship of New York, vice-presidency, and finally the presidency.

Roosevelt’s autobiography is broken up into multiple sections to capture events and

perspectives from before, during, and after the war. The first chapter, titled “Raising the

Regiment,” details the men he recruited for his planned war efforts, with greater detail given

about his Navy friend Dr. Leonard Wood. It is mentioned how patriotic the American public felt

towards the impending war in response to an American ship being sank on the coast of Havana

Cuba, an act which Spain had been accused of perpetrating. “We both felt very strongly that such

a war would be as righteous as it would be advantageous to the honor and the interests of the

nation; and after the blowing up of the Maine, we felt that it was inevitable.” (Roosevelt, 9). War

with Spain had already broken out in the Philippines and many, along with Roosevelt back at

home, felt that it was not enough and the Spanish influence in nearby Cuba had to be dealt with,

especially with the news regarding the USS Maine’s sinking. Roosevelt thought that European

influence in the western hemisphere had to go and with Cuba having already been begging for

independence from Spain for years, the opportunity for Roosevelt had to be taken. The way I

perceive this, the United States had imperialistic interests for a while now and had been waiting

for a reason to present itself so the nation could take action on expanding.
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Roosevelt’s second chapter, titled “To Cuba,” documented the voyage to the neighboring

Island nation. He described how his men were eager for what was in store for them in battle.

“Sometimes they talked of what they might do in the future and wondered whether we were to

attack Santiago or Porto Rico. At other times, as they lounged in groups, they told stories of their

past—stories of the mining camps and the cattle ranges, of hunting bear and deer, of war-trails

against the Indians, of lawless deeds of violence and the lawful violence by which they were

avenged, of brawls in saloons, of shrewd deals in cattle and sheep, of successful quest for the

precious metals; stories of brutal wrong and brutal appetite, melancholy love-tales, and memories

of nameless heroes—masters of men and tamers of horses.” (Roosevelt, 66). The soon to be

called Rough Riders were about 1000 men in numbers and they travelled towards Tampa,

Florida where they were to depart. The six-day journey was met with choppy water that caused

some boats carrying ammunition and food to capsize, taking the lives of two soldiers. However,

that would not deter the other’s efforts. Upon arrival, they did not face any resistance as the

Spaniards fled the coastal town of Daiquiri they arrived in because they evacuated earlier after

being attacked by warships. The quiet arrival of the Rough Riders in Cuba likely explained the

swiftness of the Rough Rider’s conquest.

The first resistance Roosevelt and his men faced was documented in the chapter “General

Young’s Fight at Las Guasimas.” While originally a mounted Calvary as well as being called the

Rough Riders, they were forced to fight on foot when most of the horses did not make it to Cuba

as planned. There were thirty-four men wounded in the fight and eight perished, but the Rough

Riders persisted through day one of the fight, despite being low on food and supplies. The

determination of Roosevelt and his men was put on full display with this battle. “The character

of the fight put a premium upon such conduct and afforded a very severe test for raw troops
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because the jungle was so dense that as we advanced in open order, every man was, from time to

time, left almost alone and away from the eyes of his officers.” (Roosevelt, 89). The way the

Rough Riders persevered in combat through the dense jungle and lack of supplies shows how

Roosevelt’s resilient attitude was contagious as shown by his fellow Rough Riders.

The Rough Riders’ main goal of capturing the main Cuban town of Santiago was told

over within Roosevelt’s fourth chapter titled “The Calvary at Santiago.” In order to gain an edge

in the fight, Roosevelt and his men targeted Kettle Hill, also known as San Juan Hill, for the high

ground advantage over Santiago and the neighboring Spanish fort El Caney. “The Ninth

Regiment was immediately in front of me, and the First on my left, and these went up Kettle Hill

with my regiment. The Thirds Sixth, and Tenth went partly up Kettle Hill (following the Rough

Riders and the Ninth and First), and partly between that and the block-house hill, which the

infantry were assailing. General Sumner in person gave the Tenth the order to charge the hills;

and it went forward at a rapid gait.” (Roosevelt, 127). This advance by the Rough Riders came

from all sides of the hill, overwhelming the Spanish forces. The fearless attack that on Kettle Hill

that began with Roosevelt displays how fearless the man was. Nothing in his way ever phased

him and his battle-ready temperament was evident in him and his men.

The battle for Santiago carried over into the next chapter of Roosevelt’s autobiography,

titled “In the Trenches.” Out of all the fights the Rough Riders’ faced, none would have more

casualties than the battle for Kettle Hill, as eighty-nine men have been killed or wounded. Yet as

always, the rough riders would persevere. The fight on both Spanish and American ends shifted

towards the utilization of trench warfare. The two sides exchanged fire and neither seemed to be

gaining anything from it, as the Spaniards and Americans were stuck where they were. Roosevelt

assembled a group of soldiers consisting of some men from each of the regiments in an attempt
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to dig in the direction of the Spanish trenches while the rest of the soldiers kept the Spaniards

pinned with cover fire. “I dug a long, zigzag trench in advance of the salient of my line out to a

knoll well in front, from which we could command the Spanish trenches and block-houses

immediately ahead of us.” (Roosevelt, 186). The quick thinking of Roosevelt made the biggest

difference and arguably was the deciding factor in the war overall. Roosevelt’s plan worked and

their defeat over the Spanish was imminent, for which he would later receive a Medal of Honor.

The sixth and final chapter of Roosevelt’s book, titled “The Return Home,” discusses the

Spanish surrender and the Rough Riders’ difficulties in wake of the war’s aftermath. Many

soldiers grew sickly from yellow fever and despite winning the battle, their spirits were low.

There was no certainty that they were going to return home soon, and they made camp for the

time being to let the sick regain their health. However, upon Roosevelt’s request, this was soon

to change. “At first there was naturally some hesitation on the part of the regular officers to take

the initiative, for their entire future career might be sacrificed. So, I wrote a letter to General

Shafter, reading over the rough draft to the various Generals and adopting their corrections.”

(Roosevelt, 206). Roosevelt’s superiors listened to his requests and the spirits of his men were

lifted upon the realization that they were heading home. He cared about the well-being of his

men, and after all they have been through together, the respect Roosevelt and his fellow Rough

Riders had for each other could not be more evident.

Theodore Roosevelt’s successes during the Spanish-Cuban-American War displayed true

courage and resilience. He was a man of great character, as he persevered through many

hardships early on in his life to become someone who’s legacy should be known by every

American. His autobiography, The Rough Riders, tells his story during the Cuban conflict and

through his perspective, I was able to identify how great a man he was.
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Works Cited

Roosevelt, Theodore. The Rough Riders. Charles Scribner's Sons, 1899.