Skip to main content

The Real Story of the Rough Riders

Theodore Roosevelt and the other officers of 1st Volunteer Cavalry Regiment

Theodore Roosevelt and the other officers of 1st Volunteer Cavalry Regiment

An llustration in McClure's Magazine, 1898 Oct., p. 507."The Fight for Santiago. The "Rough Riders" charging up the San Juan Hill, July 1st, and driving the Spanish from their intrenchments"  Example of "yellow Journalism"

An llustration in McClure's Magazine, 1898 Oct., p. 507."The Fight for Santiago. The "Rough Riders" charging up the San Juan Hill, July 1st, and driving the Spanish from their intrenchments" Example of "yellow Journalism"

The soldiers and officers of the Battle of San Juan Hill - The Rough Riders are included

The soldiers and officers of the Battle of San Juan Hill - The Rough Riders are included

16 October 2011

The Rough Riders were the 1st United States Volunteer Cavalry Infantry, organized to see action during the Spanish American War of 1898. They were known as the cowboys, lead by the “Cowboy” President himself, Theodore Roosevelt.

The Original Teddy Bear

Theodore Roosevelt was never called Teddy by his close family friends and relatives, but rather Teedie as a child and T. R. as an adult. He was sickly as a child, though some suggest it was only when his father was home and as a call for attention, a personality trait that would follow him for the rest of his life. His daughter would later joke about how her father was so wont for attention that when he went to a wedding he wanted to be the bride and when he went to a funeral he wanted to be the corpse.

A very ambitious man, he had been a state assemblyman for New York, a rancher, a deputy sheriff, and a New York Police Department Commissioner before being appointed to Assistant Secretary of the Navy by President William McKinley in 1897.He had also been married twice by this time, and had five surviving children.

When the United States Battleship Maine exploded in Havana Harbor on 15 February 1898, killing over two hundred sailors, newspapers across the country called for war. The Maine had been sent to Cuba to discourage the seizure of United States' interests. These interests were plantations that American businessmen had invested millions of dollars into. President McKinley had to bow to the pressures of war, and asked for Congress to declare war in April.

Roosevelt began to build up the Navy and sent ships to Guam and the Philippines, for even though John D. Long was the Secretary, Roosevelt had been effectively running things. Shortly thereafter, he resigned from his post as Assistant Secretary. He then called upon the help of a colonel in the Army to organize a cavalry unit in order to see action. The colonel was Leonard Wood.

Doctor, doctor.... we need a doctor!

Leonard Wood was two years younger than Roosevelt. Known as “Old Poker Face” because he seldom showed expressions, Wood was also a football enthusiast, having been a player and then a coach at Georgia Tech.

Wood was also a doctor, having graduated from medical school at Harvard. He enlisted in the Army and was sent to the Southwest where he showed daring skill in attacks against the Apaches there. By the time the Spanish-American War came about, he was a personal surgeon to President William McKinley.

Even though Wood was the commander of the regiment, it was clear that Roosevelt was its natural leader. The regiment was made up of two different facets of American life, but they were the two facets that made up what Roosevelt thought was the very best of American life.

The Rough Riders

First there were the socially wealthy; men from prominent and exclusive families. These were Ivy League graduates and sports champions, lawyers, stockbrokers, bankers and wall street wiseguys. Even though they were used to servants and giving orders, Roosevelt made it clear to them that they were expected to take orders like the buck privates they were or back out before they signed up.

It should be noted that not one seemed to back out or fail to do his duty.

The backbone of the regiment were the rough and tumble. Most of these men were more comfortable on the back of a horse, and were comprised of cowboys, Native Americans, several sheriffs, a few marshals, outlaws, Civil War deserters and even Charlie Younger, the son of Bob Younger of Jesse James' gang. Many of these men were the rowdier sort, and expressed their appreciation of Roosevelt with six guns shooting rounds into the air and whoops and cheers.

Because of the influence both Roosevelt and Wood had, they were able to gain much for their regiment. Everyone in their cavalry received horses, tan cotton uniforms instead of the standard woolen uniform, and most of the men were issued newer guns and rifles as well as a Bowie knife.

Roosevelt himself led the training in San Antonio, though he had never been in the military. Many of the exercises were done by trial and error and learning was done on the fly. If the men got it right, they were rewarded by trips to the local saloon, though Roosevelt threatened to beat any man who became drunk. He became well respected and well loved. Likewise, the Rough Riders became local heroes, a regiment known for being tough and willing to fight anyone who got in their way, but also were known to be generous with those in need.

Scroll to Continue

By the end of May, the regiment was trained and was sent to Tampa, Florida to await the ships that would send them to battle. However, because those who were in charge of transportation for the war were incompetent, there was a severe miscalculation in the number of troops that could be sent over by the ships. Gear and troops had to be left behind, and Roosevelt had to fight to get his men on board, even though four companies ultimately had to stay behind. Because of the lack of space, most of the horses had to be left in Florida. Ironically the "Rough Riders" became a misnomer, for the only one of the regiment who would ride a horse into battle would be Roosevelt. His horse was named “Little Texas.”

The Rough Riders first saw battle on 24 June at Las Guásimas, on the road to Cuba's colonial capital of Santiago. The Spanish had the advantage of being well-defended and virtually invisible because of the dense jungle and smokeless powder their guns used, and several of the rough riders had been killed before someone spotted their base and the Americans were able to force a retreat. It was this battle that would help to make the Rough Riders famous, for that someone was Richard Harding Davis

Call me a "Yellow Journalist"

Richard Harding Davis was one of the nation’s best known war correspondents by the time of the battles in Cuba. He had worked with newspaper greats such as William Randolph Hurst and had idealized war reports. He had full access to the Rough Riders and helped to capitalize upon the heroism of the regiment and Theodore Roosevelt. This style of romancing war was known as yellow journalism, and Davis was a pioneer in its use.

The most well-known battle the Rough Riders participated in was the battle of San Juan Hill Heights. The antics of the Rough Riders were highly sensationalized because of Davis later.

Because of the illnesses of a few other officers, Wood had been promoted to commander, and Roosevelt was promoted to colonel, leaving him full in charge of the regiment. The objective was to take San Juan and Kettle Hills, which over looked the capital of Santiago, where the main Spanish contingent was.

To take the hills would give the Americans the advantage in the war. The Rough Riders were not alone in taking this hill. Over 15000 men from several other regiments were also tasked with this objective. At the cost of over 1500 men, the hills of San Juan and Kettle were taken on July 1.

The story goes that Roosevelt, riding Little Texas, rode into battle, daring any of the Spaniards to shoot at him. As bullets whizzed by, none dared to hit him, raising his soldiers' morale. He supposedly feared nothing, save losing his eyeglasses, for he was blind without them. The story goes on to say that because he raised the morale of the troops around him, they became fearless and invincible, which helped the Americans to take both hills, which would soon bring the war to an end. Whether that is true or a work of fiction by Davis, it galvanized the myth of the Rough Riders and Roosevelt himself.

What happened next?

Theodore Roosevelt used this fame to become elected for governor of New York in 1898 and to become William McKinley's running mate in 1900, becoming president in 1901 when McKinley was assassinated. Leonard Wood would lead a massacre of Philippine Moros in 1906. He would later become Army Chief of Staff in 1910 and establish the program that would become the ROTC program.

Works Referenced

Collier, Christopher and James Lincoln Collier. The United States Enters the World Stage: From the Alaska Purchase Through World War I: 1867-1919. Benchmark Books: New York, 2000.

Davis, Kenneth C. Don't Know Much About History: Everything You Need to Know About American History But Never Learned. Perennial: New York, 2003.

Marrin, Albert. The Spanish-American War. Atheneum: New York, 1991.

The New York Public Library American History Desk Reference. 2nd ed. Hyperion: New York, 2003

“Richard Harding Davis” NNDB: Tracking the Entire World. Soylent Communications, 2001. 16 October 2011 from

“Rough Riders” The World of 1898: The Spanish American War. Library of Congress, 22 June 2011 . 16 October 2011 from

Shenkman, Richard. Legends, Lies & Cherished Myths of American History. William Morrow: New York, 1989

Shenkman, Richard and Kurt Reiger. One-Night Stands with American History: Odd, Amusing and Little-Known Incidents. Rev. Ed. Perennial: New York, 2003.

Simkin, John. “Richard Harding Davis.” Spartacus Educational. 16 October 2011 from

Smolinski, Diane. Battles of the Spanish-American War. Reed Educational and Professional Publishing: Chicago, 2003.

Smolinski, Diane. Soldiers of the Spanish-American War. Reed Educational and Professional Publishing: Chicago, 2003.

“Spanish American War.” Encyclopedia of American History. Richard B. Morris. Harper Row: New York, 1970.

Rubel, Davis. Scholastic Encyclopedia of the Presidents and Their Times. Weincourt Press: New York, 2001

“Theodore Roosevelt.” Our Presidents. The White House, 2011. 15 October 2011 from

Weinstein, Allen and David Rubin. The Story of America: Freedom and Crisis from Settlement to Superpower. DK Publishing: London, 2002.

Wikipedia contributors. "Leonard Wood." Wikipedia, The Free Encyclopedia. Wikipedia, The Free Encyclopedia, 25 Sep. 2011. 15 Oct. 2011 from

Wikipedia contributors. "Rough Riders." Wikipedia, The Free Encyclopedia. Wikipedia, The Free Encyclopedia, 15 Oct. 2011. 16 Oct. 2011

Wikipedia contributors. "Spanish–American War." Wikipedia, The Free Encyclopedia. Wikipedia, The Free Encyclopedia, 15 Oct. 2011. 15 Oct. 2011 from

Wikipedia contributors. "Theodore Roosevelt." Wikipedia, The Free Encyclopedia. Wikipedia, The Free Encyclopedia, 14 Oct. 2011. 15 Oct. 2011 from


Hawaiian Odysseus from Southeast Washington state on June 20, 2012:

I found this Hub most interesting. Theodore Roosevelt has always been one of my favorite presidents because of his spirited way of facing life's challenges head-on. Thank you very much for sharing your research. I wish you continued success here on HubPages. Voted up and interesting!

Related Articles