The United States Army was small, understaffed, and disorganized in comparison to its status during the American Civil War roughly thirty years prior.

Following the sinking of USS Maine, President William McKinley needed to muster a strong ground force swiftly, which he did by calling for 125,000 volunteers to assist in the war.

Wood's second in command was former Assistant Secretary of the Navy Theodore Roosevelt, who later became president, a strong advocate for the Cuban War of Independence.

However, after Roosevelt joined the ranks, it attracted an odd mixture of Ivy League athletes, glee club singers, Texas Rangers, and Native Americans.

The Rough Riders would receive more publicity than any other Army unit in that war, and they are best remembered for their conduct during the Battle of San Juan Hill, though it is seldom mentioned how heavily they outnumbered the Spanish soldiers who opposed them.

Several days after the Battle of San Juan Hill, the Spanish fleet sailed from Cuba, and in only a few weeks an armistice ending the fighting was signed.

Despite the brevity of their service, the Rough Riders became legendary, thanks in large part to Roosevelt's writing his own history of the regiment and the silent film reenactments made years later.

They gathered a diverse bunch of men consisting of cowboys, gold or mining prospectors, hunters, gamblers, Native Americans, and college boys—all of whom were able-bodied and capable on horseback and in shooting.

[8] Before training began, Lieutenant Colonel Roosevelt used his political influence as Assistant Secretary of the Navy to ensure that his volunteer regiment would be as properly equipped to serve as any regular Army unit.

"They succeeded in getting their cartridges, Colt Single Action Army revolvers, clothing, shelter-tents, and horse gear ... and in getting the regiment armed with the Springfield Krag carbine used by the regular cavalry.

[4]: 1–22  Although training methods were standard, the mass mobilization of troops from diverse regions resulted in an exceptionally high death rate from disease, particularly typhoid fever.

[4]: 45 Within another day of camp being established, men were sent forward into the jungle for reconnaissance purposes, and before too long they returned with news of a Spanish outpost, Las Guasimas.

By afternoon, The Rough Riders were given the command to begin marching towards Las Guasimas, to eliminate opposition and secure the area which stood in the path of further military advance.

[11] Rough Riders on both left and right sides of the trail moved forward and eventually forced the Spaniards back to their second line of trenches.

When he suffered a gunshot wound in the spine from one of the Spaniards, another soldier mistook him as Colonel Wood from afar and ran back from the front line to report his death.

Theodore Roosevelt, deeply dissatisfied with General Shafter's lack of reconnaissance and failure to issue specific orders, became uneasy with the idea of his men being left sitting in the line of fire.

[4]: 49 As the troops of the various units began slowly creeping up the hill, firing their rifles at the opposition as they climbed, Roosevelt went to the captain of the platoons in the back and had a word with him.

The captain stood hesitant, and Colonel Roosevelt rode off on his horse, Texas, leading his own men uphill while waving his hat in the air and cheering.

Though the 10th never received the glory for the charge that the Rough Riders did, one of their commanders—Captain "Black Jack" Pershing (who later commanded American troops in World War I)—was awarded the Silver Star.

[citation needed] The Rough Riders played a key role in the outcome of the Spanish–American War by assisting the American forces in forming a constricting ring around the city of Santiago de Cuba.

Before they returned to their homes across the country, Colonel Roosevelt gave them a short speech commending their efforts, expressing his profound pride, and reminding them that although heroes, they would have to integrate back into normal society and work as hard as everyone else.

[5]Roosevelt would go on to be a strong proponent for Oklahoma, New Mexico, and Arizona's statehood during his time in the Oval Office, even making it a plank of the 1900 Republican party platform.

The stamp depicts Captain William Owen "Bucky" O'Neill, who was killed in action while leading troop A at the Battle of San Juan Hill, July 1, 1898.

[26] Just after the United States entered the war against the Central Powers, the U.S. Congress gave Roosevelt the authority to raise up to four divisions similar to the Rough Riders.

In his book Foes of Our Own Household (1917), Theodore Roosevelt explains that he had authorization from Congress to raise four divisions to fight in France, similar to his earlier Rough Riders, the 1st United States Volunteer Cavalry Regiment and to the British Army 25th (Frontiersmen) Battalion, Royal Fusiliers.

He had selected 18 officers (including Seth Bullock, Frederick Russell Burnham, James Rudolph Garfield, John M. Parker, and Henry L. Stimson) and directed them to actively recruit volunteer troops shortly after the United States entered the war.

With the help of John Hays Hammond, the New York-based Rocky Mountain Club enlisted Major Burnham to raise the troops in the Western states and to coordinate recruitment efforts.

Outside the volunteer division, one of Roosevelt's most trusted officers from the Rough Riders, Brigadier General John Campbell Greenway, served in the 101st Infantry Regiment.

[28] More than anyone else, William Frederick Cody, better known as Buffalo Bill, can be credited with helping to create and preserve the dramatic myth of the Rough Riders and the American Old West.

The miniatures game Warhammer 40,000 has a regiment of the Imperial Guard, the Imperium of Man's main military, bearing the name of Attilan Rough Riders, that specializes in cavalry.