T. R. the Rough Rider: Hero of the Spanish American War

Colonel Theodore Roosevelt
Colonel Theodore Roosevelt in Cuba- 1898

Theodore Roosevelt Collection, Houghton Library, Harvard University

Among Theodore Roosevelt's many lifetime accomplishments, few capture the imagination as easily as his military service as a "Rough Rider" during the Spanish-American War. America had become interested in Cuba's liberation in the 1890s as publications portrayed the evil of Spanish Rule. No one favored Cuban independence more than Roosevelt. As Assistant Secretary of the Navy, he beat the war drum and prepared the Navy for war with Spain. The battleship USS Maine was dispatched to Havana, Cuba. After a few quiet months, anchored in Havana Harbor, the Maine suddenly exploded, killing 262 American sailors. Spain denied blowing up the Maine, but a US Navy investigation concluded that the explosion was caused by a mine. The cause of the explosion remains a mystery, but American journalists and Assistant Secretary Roosevelt, at the time, felt certain that it was a Spanish act of war. Shortly thereafter, war was declared.

Roosevelt served gallantly during this brief conflict, which lasted from May to July, 1898. An eager Roosevelt resigned his post of Assistant Secretary of the Navy and petitioned Secretary of War Alger to allow him to form a volunteer regiment. Although he had three years of experience as a captain with the National Guard, Roosevelt deferred leadership of the regiment to Leonard Wood, a war hero with whom he was friendly. Wood, as Colonel, and Roosevelt, as Lt. Colonel, began recruiting and organizing the First U.S. Volunteer Cavalry. They sorted through twenty-three thousand applications to form the regiment! Roosevelt's fame and personality turned him into the de-facto leader of this rag-tag group of polo players, hunters,cowboys, Native Americans, and athletic college buddies. The regiment of "Roosevelt's Rough Riders" was born.

The Rough Riders participated in two important battles in Cuba. The first action they saw occurred at the Battle of Las Guasimas on June 24, where the Spanish were driven away. The Rough Riders lost seven men with thirty-four wounded. Roosevelt narrowly avoided bullets buzzing by him into the trees, showering splinters around his face. He led troops in a flanking position and the Spanish fled. American forces then assembled for an assault on the city of Santiago through the San Juan Hills. Colonel Wood was promoted in the field, and in response, Roosevelt happily wrote,"I got my regiment."

The Battle of San Juan Heights was fought on July 1, which Roosevelt called "the great day of my life." He led a series of charges up Kettle Hill towards San Juan Heights on his horse, Texas, while the Rough Riders followed on foot. He rode up and down the hill encouraging his men with the orders to "March!" He killed one Spaniard with a revolver salvaged from the Maine. Other regiments continued alongside him, and the American flag was raised over San Juan Heights.

Hostilities ceased shortly after Santiago fell to siege, and the Treaty of Paris gave the United States its first possessions: Guam, Puerto Rico, and the Philippines.

The war had lasting impacts. The "splendid little war" lasted ten weeks. It destroyed the Spanish Empire and ushered in a new era of American Empire. Roosevelt's political career ignited as he returned a war hero and national celebrity. He charged on horseback to victory at Kettle Hill and, collectively, San Juan Heights, and continued riding that horse all the way to the White House just three years later. Roosevelt was posthumously awarded the Medal of Honor, one hundred years later, for what was described as "…acts of bravery on 1 July, 1898, near Santiago de Cuba, Republic of Cuba, while leading a daring charge up San Juan Hill."

Photograph of TR in his uniform on horseback

Theodore Roosevelt Collection, Houghton Library, Harvard University

We hope you enjoy reading TR's own words about the Charge on San Juan Hill, or his reflections on the Rough Riders and the images that accompany them. If you are primarily interested in images relating to Theodore Roosevelt's experience in Cuba, please visit our Spanish American War & Rough Riders photo album!


The video shown below this text is of Theodore Roosevelt leaving his job as Assistant Secretary to the Navy. It is a silent film, apart from the introduction, which informs the viewer that this video is from the Library of Congress. In the scene, TR, in formal dress with hat, walks down the steps of the Treasury Building in Washington, D.C. and turns and walks toward the stationary camera. The south portico of the White House is visible through trees in background. #TRleaving

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18 seconds

Theodore Roosevelt, 1897


In his own words....
Who were the Rough Riders?

Excerpts taken from the The Rough Riders by Theodore Roosevelt

Image of three men sitting in front of tents in an encampment.
Lieutenant Colonel Theodore Roosevelt (left) with Colonel Wood (center)

Theodore Roosevelt Collection, Harvard College Library

"Secretary Alger offered me the command of one of these regiments. If I had taken it, being entirely inexperienced in military work, I should not have known how to get it equipped most rapidly, for I should have spent valuable weeks in learning its needs, with the result that I should have missed the Santiago campaign, and might not even have had the consolation prize of going to Porto Rico. Fortunately, I was wise enough to tell the Secretary that while I believed I could learn to command the regiment in a month, yet that it was just this very month which I could not afford to spare, and that therefore I would be quite content to go as Lieutenant-Colonel, if he would make Wood Colonel. This was entirely satisfactory to both the President and Secretary, and, accordingly, Wood and I were speedily commissioned as Colonel and Lieutenant-Colonel of the First United States Volunteer Cavalry." (pp.6 -7)
Photograph of rough riders on horseback


"But owing to the fact that the number of men originally allotted to us, 780, was speedily raised to 1,000, we were given a chance to accept quite a number of eager volunteers who did not come from the Territories, but who possessed precisely the same temper that distinguished our Southwestern recruits, and whose presence materially benefited the regiment. We drew recruits from Harvard, Yale, Prince ton, and many another college; from clubs like the Somerset, of Boston, and Knickerbocker, of New York; and from among the men who be longed neither to club nor to college, but in whose veins the blood stirred with the same impulse which once sent the Vikings over sea." (p. 9-10)
Set of 8 uniformed men (rough riders) sitting in pose for a group photo. 4 men sit in the front row on chairs. The one to the farthest left has crutches. 4 other men stand in uniform behind the first row of sitting men.
8 Rough Riders sitting for portrait.

Theodore Roosevelt Collection, Harvard College Library

"Then I went down to San Antonio [Texas] myself, where I found the men from New Mexico, Arizona, and Oklahoma already gathered, while those from Indian Territory came in soon after my arrival. These were the men who made up the bulk of the regiment, and gave it its peculiar character. They came from the Four Territories which yet remained within the boundaries of the United States; that is, from the lands that have been most recently won over to white civilization, and in which the conditions of life are nearest those that obtained on the frontier when there still was a frontier...." (p. 14-15)

"All—Easterners and Westerners, Northerners and Southerners, officers and men, cow-boys and college graduates, wherever they came from, and whatever their social position—possessed in com mon the traits of hardihood and a thirst for adventure. They were to a man born adventurers, in the old sense of the word." (p. 19)

"The life histories of some of the men who joined our regiment would make many volumes of thrilling adventure." (p. 24)
Image of two soldiers portraits next to one another
Captain Bucky O'Neill (left) & Captain Allyn Capron (right)

Image published in TR's Rough Riders

"There was Bucky O'Neill, of Arizona, Captain of Troop A, the Mayor of Prescott, a famous sheriff through out the West for his feats of victorious warfare against the Apache, no less than against the white road-agents and man-killers....Allyn Capron, who was, on the whole, the best soldier in the regiment. In fact, I think he was the ideal of what an American regular army officer should be. He was the fifth in descent from father to son who had served in the army of the United States, and in body and mind alike he was fitted to play his part to perfection. Tall and lithe, a remarkable boxer and walker, a first-class rider and shot, with yellow hair and piercing blue eyes, he looked what he was, the archetype of the fighting man. He had under him one of the two companies from the Indian Territory; and he so soon impressed himself upon the wild spirit of his followers, that he got them ahead in discipline faster than any other troop in the regiment, while at the same time taking care of their bodily wants. His ceaseless effort was so to train them, care for them, and inspire them as to bring their fighting efficiency to the highest possible pitch. He required instant obedience, and tolerated not the slightest evasion of duty; but his mastery of his art was so thorough and his performance of his own duty so rigid that he won at once not merely their admiration, but that soldierly affection so readily given by the man in the ranks to the superior who cares for his men and leads them fearlessly in battle." Roosevelt, Theodore, Rough Riders, (p.18-19)
Profile image of Wm. Pollock, Pawnee Indian, on horseback wearing Rough Rider uniform
Pollock on Horseback in uniform

Theodore Roosevelt Collection, Houghton Library, Harvard University

"From the Indian Territory there came a number of Indians —Cherokees, Chickasaws, Choctaws, and Creeks. Only a few were of pure blood. The others shaded off until they were absolutely indistinguishable from their white comrades; with whom, it maybe mentioned, they all lived on terms of complete equality…One of the gamest fighters and best soldiers in the regiment was Pollock, a full blooded Pawnee. He had been educated, like most of the other Indians, at one of those admirable Indian schools which have added so much to the total of the small credit account with which the White race balances the very unpleasant debit account of its dealings with the Red. Pollock was a silent, solitary fellow—an excellent pen man, much given to drawing pictures." Roosevelt, Theodore Rough Riders (p. 20-21)
baclk and white published image of General Sumner on horseback, in uniform

Rough Riders by Theodore Roosevelt

In his own words....
The charge on San Juan Hill, Cuba

Excerpts taken from the The Rough Riders by Theodore Roosevelt

"I sent messenger after messenger to try to find General Sumner or General Wood and get permission to advance, and was just about making up my mind that in the absence of orders I had better 'march toward the guns,' when Lieutenant Colonel Dorst came riding up through the storm of bullets with the welcome command 'to move forward and support the regulars in the assault on the hills in front.' " (p.125)
Black and white drawing by Remington depicting the Charge on San Juan Hill. Men are engaged in battle, some run foeward. Others have fallen.

Rough Riders by Theodore Roosevelt

"In the attack on the San Juan hills our forces numbered about 6,600.* There were about 4,500 Spaniards against us. Our total loss in killed and wounded was 1,071. Of the cavalry division there were, all told, some 2,300 officers and men, of whom 375 were killed and wounded. In the division over a fourth of the officers were killed or wounded, their loss being relatively half as great again as that of the enlisted men—which was as it should be. was as it should be. I think we suffered more heavily than the Spaniards did in killed and wounded (though we also captured some scores of prisoners)." (p.156-158)
Black and white image of the original Oath of office that TR took when he was promoted to Colonel

National Archives

When Colonel Wood gets promoted, so does Theodore Roosevelt. This is an "Oath of Office" certifies Theodore Roosevelt's promotion to colonel of the First Volunteer Cavalry. (NARA, Records of the Adjutant General's Office, 1780s-1917, RG 94)

Text includes:
I Theodore Roosevelt having been appointed a Colonel First Volunteers Cavalry in the military service of the United States, do, solemnly swear (or affirm) that I will Support and defend the Constitution of the United States against all enemies, foreign or domestic; that I will bear true faith and allegiance of the same; that I take this obligation freely, without any mental reservation or purpose of evasion; and that I will well and faithfully discharge the duties of the office on which I am about to enter: So help me God.
[Signed] Theodore Roosevelt col 1st U.S.V.
Sworn to and subscribed before me, at Santiago de Cuba, this 31st day of July, 1898
[signed] John H Parker

Want to explore more images & information about the War of 1898 (Spanish-American War)? Check out the Theodore Roosevelt Collection at Harvard College, the Library of Congress, & National Archives

For a short video of Theodore Roosevelt's Rough Riders, click here.

For a short video of troops disembarking, click here.

click here to explore the Library of Congress collection of short videos relating to the Spanish American War.

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Last updated: November 19, 2020

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