StMU Research Scholars

Teddy and a Splendid Little War

Within the historic city of San Antonio, set between the Alamo and the River Walk, stands the Menger Hotel, a Victorian-era gem. This quiet antique hotel played center stage to the changing destiny of the United States. In 1898, recruits trained nearby and chanted the battle cry, “Remember the Maine, to Hell with Spain.” These men formed the 1st United States Volunteer Cavalry, more famously known as the Rough Riders. Theodore Roosevelt served as one of its founders.

Theredore “Teddy” Roosevelt in his military uniform | 1900 | Courtesy of Wikimedia

Roosevelt was born on October 27, 1858. In his youth, Roosevelt was small and suffered from asthma. Despite these obstacles, he had an accomplished life.1 Nevertheless, Roosevelt might suggest he overcame the ailments of his youth through sheer force of will. During his early adult life, he became an accomplished hunter and naturalist. Roosevelt attended Harvard studying natural history, and graduated Magna Cum Laude.2

Roosevelt went into politics almost immediately after his graduation, and took up the study of law. He shortly became tired of living as a politician, and said, “self-interest is a cardinal sin against the people in a democracy.”3 On February 14, 1884, both Roosevelt’s mother Martha Bulloch and wife Alice Lee died due to unrelated reasons. These events led him to enter into a deep depression and fueled his desire to change careers. Roosevelt then left his old life behind and moved to the Dakota Territory. During his time on the frontier, Roosevelt settled on a ranch and improved himself by riding and hunting. Roosevelt later wrote that working alongside other men “took the sob out of me [Roosevelt].”4

Roosevelt settled into the Dakota Territory and became a deputy sheriff. During his time as a lawman, he became friends with Seth Bullock, the Sheriff of Deadwood. They met while searching for the same horse thief. Bullock later served as an officer in the Rough Riders. Roosevelt gained fame as a deputy. On one occasion, he captured three boat thieves on a frozen river. Rather than letting vigilantes hang them, Roosevelt maintained custody and escorted them to Dickinson, North Dakota for their trial. For two days, Roosevelt traveled with the criminals, reading Tolstoy’s works to keep himself awake for the entire journey. “I [Roosevelt] kept guard over three prisoners who were huddled into a sullen group some 20 yards off—just the right distance with a buckshot in the double-barrel.”5

Roosevelt finally returned to New York in 1895; but, he did not return to politics. The mayor of New York City appointed him as the Police Commissioner. During his two years of service, Roosevelt worked to stamp out corruption and reshape the police force. Roosevelt and a friend often took secret night walks to inspect the police officers on duty and make sure they were doing their job.6 The night walks had such a success that members of the press started to follow them on their patrols. Naturally, the presence of the entourage forced the secret night walks to end.

President McKinley appointed Roosevelt as the Assistant Secretary of the Navy during the spring of 1897. Roosevelt joined a growing faction in the Federal Government to expand the U.S. military in order to properly enforce the Monroe Doctrine. This group advocated for the removal of Spain from Cuba through diplomacy or force.7 This change of policy required a strong navy with ocean-going battleships, dozens of cruisers, scores of lighter ships, and a large reserve of trained officers and sailors to operate the new fleet. However, during this time, the government only allowed a small Federal Army and Navy. The U.S. relied upon state militias for its main armed forces during this peacetime. Many officers and governmental officials wished for a military that could compete with the European and South American powers. However, the country was still recovering from the Civil War that ended thirty years prior. Tensions with Spain increased rapidly through a course of events centering on Cuba.  It would only take a spark to set off a wildfire.

The Spark

The Cuban War of Independence began in 1895. Cubans sought economic reforms that could only be achieved through an independent Cuba.8 Rebels relied on using guerrilla tactics to fight the Spanish colonial forces. In response, the Spanish Crown assigned General Valeriano Weyler y Nicolau as the Governor-General of the region. Weyler was a brilliant military leader and disciple of William T. Sherman.

General Valeriano Weyler y Nicolau, Governor-General of Cuba from 1896-1897 | Courtesy of Wikimedia Commons

Weyler served as the military attaché of Spain in Washington during the American Civil War. Weyler believed that the best way to end a conflict was quickly, and by any means necessary, believing this to be the merciful course of action. He suppressed the insurgencies with the full authority of Spain. Traditional strategies met with minimal effectiveness—causing Weyler to use more aggressive means. These tactics included forcing men, women, and children to live in what some would consider concentration camps.9 Weyler’s actions compelled Americans to support Cuban independence publicly. Americans sympathized with the Cuban cause and saw a potential for increased economic benefits from an independent Cuba. American organizers, medical workers, and combatants volunteered in Cuba. The United States even sent a warship, the U.S.S. Maine, into Havana Harbor.10

For three weeks, the U.S.S. Maine’s first station in Havana Harbor was quiet; no one suspected what was to happen next. The night of February 15, 1898, started as an ordinary evening. At 9:40 pm, the warship’s forward magazine suddenly detonated, causing the U.S.S. Maine to buckle, and sink within minutes. Only the main mast remained above the water. This tragedy resulted in the death of 260 sailors leaving only 75 survivors.11

A popular new print and textbook illustration of USS Maine forward magazine exploding in Havana bay in Cuba | 1898 | Courtesy of Wikimedia Commons


Despite the Spanish lending assistance through the nearby Alfonso XII, the press claimed it was a Spanish attack via a well-placed sea mine.12 Interestingly, evidence suggests some officials from the navy suspected the explosion resulted from a coal fire—a common incident for ships. Nevertheless, the incident report from 1898 reported an inverted V hole on the Maine’s hull near the magazine. President McKinley handed the information to Congress on April 11, 1898. Fourteen days later, the United States officially declared war on Spain.13  Congress immediately ordered the expansion and mobilization of the military. The United States set out to end the last European influence in the New World and enforce the Monroe Doctrine.

­­­­­­­The Mobilization

At the start of the Spanish American War, the United States commanded a small, somewhat underfunded military force. Congress raised volunteer units to serve in the conflict. The Secretary of War, Russell A. Alger, offered Roosevelt a commission to command a new regiment despite his limited military experience. Both the President and the Secretary of War believed that Roosevelt would learn fast. Leonard Wood and Roosevelt were commissioned as the commanding officers of the 1st Volunteer Cavalry Regiment. They left for San Antonio to recruit and train men for the regiment.14

New printing of the Rough Riders after San Juan Hill | 1898 | Courtesy of Wikimedia Commons

The 1st Volunteer Cavalry Regiment had the best raw talent and the most diverse soldiers among the three volunteer cavalry regiments. Wood and Roosevelt recruited men from the frontier to ivy league schools. Recruits also included lawmen, the outlaws they hunted, and veterans from both sides of the American Civil War. Native Americans served in the unit as well.15 In his journal, Roosevelt specifically praised these groups, noting Cherokees, Chickasaws, Choctaws, Pawnee, and Creeks were some of the best soldiers in the regiment.16 While training and organizing the new regiment in San Antonio, the press coined the name Rough Riders. “At first, we [the Rough Riders] fought against the use of the term, but to no purpose; and when finally, the Generals of Division and Brigade began to write in formal communication about our regiments as the ‘Rough Riders,’ we adopted the term ourselves.”17 Roosevelt wrote how he immensely enjoyed San Antonio, Texas.  While training in the vicinity of the Alamo, frontier heroes, such as Crocket and Bowie blessed the Rough Riders for success. 18

During this conflict, Spanish forces dwarfed the American military in size and experience.19 Wood and Roosevelt knew the Rough Riders would be at a severe disadvantage. Successful frontier tactics known by the recruits would likely be insufficient when encountering the Spanish Army. The Rough Riders needed to be ready to face an army of highly experienced Spanish troops waiting for them in Cuba.

On May 29th,1898, the Rough Riders received orders to ship out by train to Tampa, Florida. To reach Tampa, there was a single rail line, with several trains trying to leave and enter the city at once, causing confusion and delay multiple times while assembling the 5th-Corps.20 The Rough Riders finally reached the 5th Army-Corps after 48 hours of travel.

For the first time in U.S. military history, the Federal Forces prepared for an overseas campaign. This put a major strain on the military logistics system and the U.S. Transportation Corps. They were not prepared for the overseas expedition. For example, commanding officers of the 5th-Corps ordered uniforms to match the Cuban countryside and the sub-tropical heat. Mistakenly, the Army Transportation Corps shipped the subtropical tunics to Anchorage, AK instead of Tample, FL. Hence, the U.S. forces in Cuba wore light blue shirts and khakis trousers.21

Navel Development

For most of history, nations worldwide have depended on ships of wood and sail. These warships showed the wealth of empires and their power. A First-Rate Man O’ War dominated the open seas with its large armament of canons of various calibers. The H.M.S. Victory is the oldest warship still in service with the British Royal Navy as a floating museum. The H.M.S. Victory, commissioned in 1778, had a complement of 104 cannons. To provide a perspective of power, the British army only used 160 pieces of artillery during the Battle of Waterloo.22

HMS Victory at Portsmouth, England as a float museum | 2007 | Courtesy of Wikimedia Common

By the middle of the nineteenth century, ships evolved and incorporated technological advancements. The steam-powered ship first appeared during the American Civil War. The steam engine provided more powerful means of propulsion and allowed the addition of heavy armament and armor. The first confrontation of these ships was at the Battle of Hampton Roads. The ironclad C.S.S. Virginia, a converted frigate with iron plates, faced the U.S.S. Monitor, another ironclad. Although the battle itself was indecisive, those ships revolutionized naval tactics around the world and sparked a naval arms race.

Navies around the world began building heavily armed and armored warships. The Capital ships during the Spanish American War continued in this fashion. These ships followed a standard layout of two main turrets and several secondary and tertiary batteries, giving them the capacity to provide an almost constant rain of fire during combat. As technology continued to advance at a rapid pace, the U.S. incorporated advancements slowly. Prior to the Spanish-American War,  the U.S. Congress wished to keep the navy as a coastal defense fleet.

The Battle That Made a Legend

When the 5th Corps embarked for Cuba, it did so with a complement of 819 officers, over 15,000 enlisted troops, 30 civilian clerks, 89 newspaper correspondents, 11 foreign military observers, and over 2,000 horses and mules. The corps equipped themselves with artillery, mortars, Gatling guns, observation balloons, and 200 wagons.23 On June 22, 1898, the 5th Army-Corps made landfall with no opposition. That was a blessing, as the landing process was a complete disaster for the U. S. Forces. Poor logistics and lack of preparedness caused equipment to be lost or damaged. Units landed at separate times without coordination. During the chaos, an unknown soldier wrote that a group of horses and donkeys jumped off the ship and swam to shore. Many of them drowned, or swam in the wrong direction. It was not until someone called the retreat bugle that the horses and donkeys were able to find the shore.24 It was lucky that the Spanish weren’t anywhere near the landing site.

In Cuba, the U.S. faced an entire Army Group of Spanish Soldiers. The U. S. Navy was able to establish a blockade while the 5th-Corps marched on Cuba’s Capital, Santiago.  During the march to Santiago, many soldiers contracted tropical diseases, such as Malaria and Yellow Fever. Disease, and ill prepared food, led to higher casualty rates in comparison to battlefield injuries during the conflict.

The Spanish Army was a respectable modern military force and were experienced with the terrain. Spain provided their army in Cuba with the best modern weapons. The Spaniards positioned themselves outside the capital, at San Juan Hill, Kettle Hill, and the Village of El Caney. On July 1, 1898, all three locations were fought for during the famous Battle of San Juan Hill. The United States forces committed to a frontal assault on the hilltop fortifications doing what most European military officials would consider impossible—moving on foot up a hill with open ground against a well-entrenched and equally equipped and unshaken infantry.

During the battle, Roosevelt saw an opportunity on the neighboring Kettle Hill, and under no orders by his superiors, he ordered the Rough Riders to advance. Initially, they were not keen on it, until they learned that Roosevelt would be at the front of the advance. “The only way to get them to do it in the way it had to be done was to lead them myself.”25

The Charge up Kettle Hill by the Rough Riders Lead by Theodore Roosevelt on the Horse | 1898 | Courtesy of Wikimedia Commons

During the change uphill, Roosevelt rode on his horse until a Spanish soldier shot the horse from underneath him. Unshaken, Roosevelt led the rest of the way on foot. Roosevelt himself killed several Spaniards with a revolver salvaged from the U.S.S. Maine. 26 Soon Kettle Hill fell to the U.S. Forces. When the Rough Rider managed to reach the top of Kettle Hill, they joined the 10th Cavalry who had captured most of the hill. The 10th Cavalry was comprised of African-American and Native-American soldiers, commonly referred to as Buffalo Soldiers.27 Buffalo Soldiers proved themselves as very competent troops during the Spanish American War, often outperforming most of their white regiment counterparts and the Spanish opponents.

With the capture of Kettle Hill, the Rough Riders and Buffalo Soldiers used the momentum and flanked the Spanish forces of San Juan Hill, allowing a clear path to Cuba’s capital, forcing the Spanish to send out their remaining ships composed of four armored cruisers and two destroyers to steam out of port and face the blockade. The Spanish fleet engaged the U.S. blockade of four battleships, two armored cruisers, and two armed yachts. The subsequent conflict ended with the destruction of the Spanish fleet and the capture of Santiago. The Spanish force surrendered, and with the Treaty of Paris (1898), ended the Spanish American War. Additionally, this victory ended the Spanish Colonial Empire, and began the Rise of the United States.28

Rise of the United States.

America’s destiny forever changed with the signing of the Treaty of Paris (1898). Spain relinquished its overseas territories to the United States either to govern directly or indirectly. Cuba became a protectorate of the United States, while the Philippines, Guam, and Puerto Rico became territories. As the ink dried on the treaty paper, the age of American Imperialism in the western hemisphere began. 29

Political cartoon of Roosevelt Big Stick Diploma | 1905 | Courtesy of Wikimedia Commons

It was not until 1901 that the Republic Party took advantage of Roosevelt’s fame and placed him on the Vice-President’s poll, much to the unawareness of Roosevelt, and without the blessing of McKinley. Roosevelt won the campaign for Vice-President unanimously. On September 14, 1901, President McKinley became the third president to be assassinated, causing Roosevelt to become the 26th President of the United States.30

During Roosevelt’s administration, he formed the F.D.A. to prevent needless deaths due to poor food. Roosevelt also broke many business trusts and created the national parks.31

However, one of his most lasting actions was his reorganization of U.S. military politics, for he helped to standardize training and equipment for the armed forces. This included improvements in logistics. While as Assistant Secretary of the Navy, the naval officer and A.T. Mahan’s books spoke that the navy was to project a nations’ wealth and powers, which influenced him to modernizing the navy entirely.

Roosevelt ordered the Great White Fleet’s creation, the first genuinely modern naval fleet in U.S. history. It was the beginning of the American global dominance and taking active world affairs. Thanks to Theodore Roosevelt’s administration, it helped the United States to become known as the Arsenal of Democracy.

  1. Thomas Evans, The War Lovers: Roosevelt, Lodge, Hearst, and the Rush to Empire (Back Bay Books, 2011), 22.
  2. “Theodore Roosevelt at Harvard | News | The Harvard Crimson,” accessed March 18th, 2021,
  3. Theodore Roosevelt and Louis Auchincloss, The Rough Riders: An Autobiography, The Library of America: 153 (Library of America, 2004), 232.
  4. ExplosmEntertainment, “Hardcore Facts About Teddy Roosevelt,” 2021,
  5. ExplosmEntertainment, “Hardcore Facts About Teddy Roosevelt,” 2021,
  6. Theodore Roosevelt and Louis Auchincloss, The Rough Riders: An Autobiography, The Library of America: 153 (Library of America, 2004), 316.
  7. Theodore Roosevelt and Louis Auchincloss, The Rough Riders: An Autobiography, The Library of America: 153 (Library of America, 2004), 316.
  8. Albert Nofi, The Spanish- American War 1898 (Philadelphia, Pa: De Capo Press, 2001), 30.
  9. Albert Nofi, The Spanish- American War 1898 (Philadelphia, Pa: De Capo Press, 2001), 30.
  10. James R. Reckner, “Manila & Santiago: The New Steel Navy in the Spanish-American War,” International Journal of Maritime History 21, no. 2 (December 2009): 476–77.
  11. James R. Reckner, “Manila & Santiago: The New Steel Navy in the Spanish-American War,” International Journal of Maritime History 21, no. 2 December 2009: 476–77.
  12. G. O’Toole, The Spanish War: An American Epic 1898 (New York NY: W.W. Norton & Company, 1984), 30.
  13.  Fisher Louis, “Destruction of the Maine,1898,” Department of the Navy n.d, 5.
  14. Theodore Roosevelt and Louis Auchincloss, The Rough Riders: An Autobiography, The Library of America: 153 (Library of America, 2004), 10.
  15. Tandem Web Co, Teddy Roosevelt, San Antonio, and the Birth of the Rough Riders, Texas Highways (blog), October 31st, 2019,
  16. Theodore Roosevelt and Louis Auchincloss, The Rough Riders: An Autobiography, The Library of America: 153 (Library of America, 2004), 17.
  17. Theodore Roosevelt and Louis Auchincloss, The Rough Riders: An Autobiography, The Library of America: 153 (Library of America, 2004), 10.
  18. Theodore Roosevelt and Louis Auchincloss, The Rough Riders: An Autobiography, The Library of America: 153 (Library of America, 2004), 30.
  19. Albert Nofi, The Spanish- American War 1898 (Philadelphia, Pa: De Capo Press, 2001), 60.
  20. Stephen T. Messenger, “THE TRAINS STOP AT TAMPA: Port Mobilization During the Spanish-American War and the Evolution of Army Deployment Operations,” Army History, no. 104 (2017): 34–55, 46.
  21. Brian D. Blodgett, “The Difficulties In the Formation of the V Corps, 1898, Spanish American War,” The Spanish American War (website), accessed April 18, 2021,
  22. Simple history, A Titan of Pre-Industry: The Ship of the Line, 2018,
  23. G. O’Toole, The Spanish War: An American Epic 1898 (New York NY: W.W. Norton & Company, 1984), 254.
  24. “A Soldier’s Account of the Spanish-American War (1898) | Encyclopedia.Com,” accessed April 18, 2021,
  25. ExplosmEntertainment, “Hardcore Facts About Teddy Roosevelt,” 2021,
  26. Roosevelt, Theodore, Louis Auchincloss, and Theodore Roosevelt, The Rough Riders : An Autobiography, The Library of America: 153 (Library of America, 2004). 369.
  27. Albert Nofi, The Spanish- American War 1898 (Philadelphia, Pa: De Capo Press, 2001), 146.
  28. Knowledgia, The Spanish-American War – Explained in 11 Minutes, 2020,
  29. G. O’Toole, The Spanish War: An American Epic 1898 (New York NY: W.W. Norton & Company, 1984), 383.
  30. Theodore Roosevelt and Louis Auchincloss, The Rough Riders: An Autobiography, The Library of America: 153 (Library of America, 2004), 436.
  31. Jack Rackam, “America’s Manliest President | The Life & Time of Theodore Roosevelt”, 2020,

14 Responses

  1. Seth, I liked the reminder of the San Antonio connection at the beginning of your article. Your article highlighted Teddy Roosevelt’s early career which gives us a foundation of his character and his motivation to excel in whatever he pursued. The United States was at a disadvantage at the start of the Spanish American War. Roosevelt had no military experience, but led the battle up Kettle Hill first on horse and then on foot. Capture of Kettler Hill and then later San Juan Hill allowed for overall success in the war. The article was informative on Roosevelt’s role in the war and then ended with a summary of his accomplishments as President of the United States. Great Job!

  2. This was such a great and well-written article. I have always loved Teddy D. Roosevelt and his bravery in the face of battle. I believe during the battle of Kettle Hill, the men were cowering and crawling behind him, and he stated that they were aiming for him since he was on a horse and for them to stand up and run and stop being cowards. He was such a brave man. Again excellent article, very informative!

  3. The article you did goes more in-depth about the background of Theodore Roosevelt and what led him to become the president of the United States, rather than his terms as president, which I liked. The way you open his article with an introduction, foreshadowing the idea that the “destiny” of America that Roosevelt would adopt, keeps the reader encapsulated with the passage. You break down every major life-changing event that occurred in Roosevelt’s life and illustrate the obstacles he faced down to the nail. As Roosevelt is a personal favorite president, I would say I rather enjoyed the article.

  4. This a good article. I found your article title to be fun and creative. I also found your article very informative. I never knew Teddy Roosevelt was a very active person. I didn’t even know he was a politician till I read this article. Also, his involvement in the Spanish American war was quite surprising. They offered him a commission to command a regiment, even though he had limited experience.

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