What were Theodore Roosevelt’s Rough Riders?

Teddy Roosevelt was one of the most memorable and influential Presidents of the United States. However, some of his actions and projects went down in history even before he became President.

When Roosevelt was still the Assistant Secretary of the United States Navy, he gave his resignation in 1898 in order to organize a group called the Rough Riders.

The Rough Riders are known as the first voluntary kind of cavalry during the Spanish-American War. The United States was in arms against Spain due to the latter’s colonial policies regarding Cuba. Theodore Roosevelt got together a group consisting of miners, Native Americans, cowboys, and law enforcement officials, all under the name of Rough Riders. This group was part of Kettle Hill’s capture, also assisting in the capture of San Juan Ridge. For this, they had to charge up the highest point of the area, which was San Juan Hill. This charge on the 1st of July, 1898, is probably what they’re most remembered for today.

What Exactly Were the Rough Riders? 

Roosevelt and the Rough Riders were a motley group of ‘soldiers’, though they didn’t start out as an official part of any army. During the Spanish-American war, they were among the most public characters. When we watch old Westerns today, one of the most ubiquitous tropes is the posse of heroes riding after the villains in a dust cloud. That’s more or less the overall portrayal of the Rough Riders during the war.

While the Rough Riders aren’t responsible for single-handedly winning the war, they were instrumental in the overall victory. A lot of soldiers and whole cavalry units gave up their lives while fighting, with the Rough Riders being right in the center of action.

The Original Plan for the Rough Riders

The Original Plan for the Rough Riders

While the Rough Riders were a well-known name due to the Spanish-American War, the plan for this unit was simply to get together men from New Mexico, Oklahoma, Arizona, and the Indian Territory. Once Theodore Roosevelt joined this group, however, it turned into a place for a much more diversified mixture of troops. There were Ivy League athletes, glee-club singers, Indians, and Texas Rangers among many other demographics all under the banner of Rough Riders. Theodore Roosevelt’s rough riders certanily looked the part knowing how to wear a cowoby hat and dress for rough riding.

Supplies Given to the Rough Riders

Supplies Given to the Rough Riders

The commander of this volunteer unit was Colonel Leonard Wood. Once Roosevelt joined him, they both trained the men very well and supplied them properly at the San Antonio camp in Texas. Their training was so effective that the unit was allowed to go into the main action, which was very unusual for volunteer companies.

The Rough Riders went to Tampa in May and to Santiago de Cuba in June. There, they became part of the Fifth Corps, which was another enthusiastic unit with good training and supplies.

Before the training even started, Colonel Roosevelt made use of his political influence to make sure that his regiment was properly supplied with enough to be part of any Army unit. This is how the Rough Riders got proper guns, cartridges, revolvers, horse gear, and shelter-tents. They also made use of Bowie knives. At the last minute before they left for war, a rich donor sent them a gift of two modern gas-operated machine guns.

The Uniform of the Rough Riders

While the regiment was as well-supplied as any regular Army unit, the uniforms they wore set them apart. This consisted of a blue flannel shirt, a slouch hat, leggings, boots, brown trousers, and handkerchiefs on their necks. The idea was to give the impression of a cowboy cavalry, with the somewhat rough appearance giving them the name of ‘Rough Riders’.

Training of the Rough Riders

The training for the Rough Riders was fairly standard. They worked on protocol, military drills, conduct, etiquette, and obedience. The men themselves were eager about getting all the necessary knowledge, so the training process went fairly smoothly.

The mission here was not to train these men in using the saber, like the regular cavalry did. They didn’t have any experience with this weapon, so the revolvers and cartridges were both primary and secondary weapons for them.

Most of the men were already trained in riding a horse, so the officer gave them refinement in shooting while riding, practicing formations, and riding in skirmishes as well. The men of higher  ranks also studied drills and tactics from books in order to better lead others. When physical drills were not possible due to inadequate space while traveling, the men read more books to prepare for war. Roosevelt himself mentioned this group in the books he wrote.

The Spanish–American War

The Spanish–American War

At the end of May 1898, the Rough Riders and their animals (number 1060 and 1258 respectively) traveled from the Southern Pacific railroad to Tampa, Florida. From there, they would go to Cuba. Major General William Rufus Shafter, under pressure from Washington D.C., ordered the troops to dispatch before there were any proper arrangements for traveling storage. This meant that only 8 out of 12 companies of Rough Riders could leave Tampa for the war, with most of the mules and horses left behind as well.

Lieutenant-Colonel Roosevelt felt genuine sorrow for the men they had to leave behind, but this situation also resulted in prematurely weakening the men. Around a quarter of the group had already succumbed to yellow fever and malaria. As a result, the surviving troops that went to Cuba were significantly low in both morale and manpower.

Once the Rough Riders got to Cuba, they set up camp with what they had. They were deprived of adequate transportation; if the mule train had been allowed, the complete cavalry division could have received proper supplies.

Later on, Roosevelt would write that each Rough Rider was only carrying enough food to last them for a few days. Most of them had heavily trained the horses and depended on them, but were not allied to bring them along. They were not used to marching long distances in hot, dense, and humid conditions. Ultimately, the men were at a severe disadvantage before they had even seen a single battle.

The Battle of Las Guasimas

The Battle of Las Guasimas

This battle began on June 24, 1898, and the Rough Riders showed their heroic stand then. Las Guasimas was a Spanish outpost, which they soon discovered after setting up camp. In the afternoon, the Rough Riders began marching towards this outpost in order to secure the place and do away with their opposition. Once they reached their destination, they decided to attack early in the morning.

There were other cavalries alongside the Rough Riders here, including the 1st U.S. Volunteer Cavalry, the 1st U.S. Regular Cavalry and the 10th U.S. Regular Cavalry .

The Spanish had an advantage here, as they knew the complex ways of the area much better than the Americans. They could predict where the American soldiers will be traveling by foot and where they could fire in order to cause the most damage. They also knew how to spread out in order to be difficult to pinpoint.

The Spanish soldiers also had smokeless powder, which made it harder for the Americans to determine their exact position. The jungle was also very thick, so no one could see ahead too far.

However, the Rough Riders managed to move forward on both sides of the trial and forced the Spanish back to the second line of trenches. They continued  on, making the Spanish withdraw from their last positions as well. The A Troop Rough Riders joined hands with the regal cavalry and assisted in seizing the long hill’s Spanish positions by 9:30 in the morning.

In the beginning of this battle, a newspaper man suffered a gunshot wound and died due to it. However, one of the men mistook him for Colonial Wood, who was leading the regiment. He reported back to Roosevelt, who took control as the colonel of the cavalry. His leadership charisma managed to gather the troops and lead them to victory. At the end of the battle, the Rough Riders had 31 wounded and 8 dead. After the battle, Roosevelt found Colonel Wood alive and well; he then stepped down and became the lieutenant–colonel again.

By the time this battle came to an end, the United States was in complete control of this outpost. General Shaftner made the men stay in position for some more days until more supplies could be brought in. During this time, some of the men caught a fever and passed away. The Rough Riders were very active in these six days, caring for the injured and burying the fallen men from both armies.

General Joseph Wheeler was among the ill men, so Brigadier General Samuel Sumner became the commander of the cavalry. Colonel Wood took the position of brigadier general over the second brigade. Finally, Roosevelt became the colonel for the Rough Riders.

The Battle of San Juan Hill

The Battle of San Juan Hill

After taking over the outpost, the men were ordered to march eight miles on the road to Santiago. Their initial mission was to get to San Juan Heights, which had a defense of around a thousand Spanish soldiers. The American soldiers were to occupy the enemy there, with the Rough Riders joining in mid-battle.

The battle of San Juan Heights started with the American artillery attacking the Spanish. The Spanish duly returned fire, which meant that the Rough Riders had to avoid the shells as well. Roosevelt and the Rough Riders moved to Kettle Hill along the river, but they were in a vulnerable position. Spanish rifles were firing much more quickly than American ones, but their Mauser bullets only inflicted small and clean wounds. While they hit several  men, only a few were seriously injured or killed.

At this point, Theodore Roosevelt was unhappy with the non-specific order of General Shaftner. He didn’t want to leave his men like sitting ducks in Spanish fire. This is why Roosevelt decided to send messengers to the generals and get orders for advancing further. Once he got the orders for assisting the regular in the attack on the hill, Roosevelt got on horseback so that he could supervise more efficiently.

Roosevelt chided both his men and other soldiers to stay firm and accompany him in the charge. He also promised to shoot any soldiers if they turned back, with the Rough Riders chanting that he did keep his promises. This chant was probably in  jest, but had the effect of getting the soldiers to willingly join the assault.

The Rough Riders enthusiastically and obediently followed Roosevelt up the hill, stirring up other men from various units. The charge then consisted of several short rushes by both regulars as well as Rough Riders. Kettle Hill was taken in just 20 minutes, though there were a lot of casualties. Within another hour, the US cavalries were able to capture the whole of San Juan Heights.

Colonel Roosevelt saw that the hammering noise of the American’s Gatling guns was raising the men’s spirits. He later described the sound as ‘inspiring’ in one of his writings. There are also other books that describe the incident; here is some suggested reading that can provide more information on Theodore Roosevelt.

The Siege of Santiago

The Rough Riders were a key element in the Spanish-American War outcome. They helped the American forces by making a ring around Santiago de Cuba and achieving the ultimate goal of capturing San Juan Heights. From there, they could more easily attack Santiago, which was the Spanish military’s strong point.

The United States were also able to drive Spanish cruisers out of the port by moving in on Santiago city from different directions. Just a couple of days after the capture of San Juan Heights, the US Navy was able to destroy the Caribbean cruiser fleet located at Santiago Bay. This was a great blow to the Spanish military, as they relied heavily on their naval power.

The Aftermath of the War

The Aftermath of the War

The Rough Riders landed in Long Island on August 14th, where they met their men who had to be left behind. Colonel Roosevelt noted that a lot of these men were feeling guilty for not having taken part in the battles in Cuba. He then gave a statement that those who had to stay also did their duty, just as well as those who were able to serve.

The Rough Riders stayed in Montauk for some time and got medical care. A lot of them had contracted malaria in Cuba, which is why it was then called the Cuban fever. Some men had passed away in Cuba due to this, while others were brought to America in a makeshift kind of quarantine. The fever was recurring and very strong, so some men also passed away after they got home while others suffered from exhaustion and lost a lot of weight.

Mascots Representing the Rough Riders

The time spent in Montauk was also one of celebration. The Rough Riders regiment was honored with at least three mascots to represent them. One was a mountain lion named Josephine, who was brought from Arizona to Tampa by certain troops. The second was a war eagle named after Colonel Roosevelt himself and brought by some troops from New Mexico. The third was a dog named Cuba whom they had brought from overseas. There was also a boy who was a stowaway on the shop to Cuba. He was found with boxes of ammunition and a rifle; then sent back before the ship left the United States. However, he was then looked after by the men who were left behind, even getting a Rough Riders uniform in his size along with honorary membership of the unit.

The men also honored their colonel for his service and strong leadership by presenting him with a bronze statue of the ‘Bronco Buster’. This small figure depicted a cowboy on a bucking horse. The statue was an apt gift for the leader of a unit with wild and dangerous horses. After this presentation,. Every man in the Rough Riders shook Roosevelt’s hand and said goodbye to him.

Disbandment of the Rough Riders

Disbandment of the Rough Riders

The official disbandment of the Rough Riders was on September 15th, 1898. In the morning, all the firearms, horse, and other equipment of the revenant was given back to the government of the United States. The soldiers bade goodbye to one another and Roosevelt’s Rough Riders were disbanded. Before the men went back home, Colonel Roosevelt made a short speech about how proud he was of them, praising their efforts, and reminding them that they still had to work hard and blend back into regular society. Many of the Rough Riders were not able to do that, as they weren’t able to get their previous jobs back. This was mostly due to their illness or injuries. Some wealthy supporters did donate something to help out the veterans who needed it, but many of them had too much pride to accept any money.

Reunions of the Rough Riders

Rough Riders 1948

The first reunion of the men in the unit was in the Plaza Hotel, Las Vegas, New Mexico, in 1899. Theodore Roosevelt was then the Governor of New York, and attended the event himself. He also made a speech about how the Southwesterners and New Mexicans have contributed to his Rough Riders, saying:

“The majority of you Rough Riders came from the Southwest. I shall ever keep in mind the valor you showed as you charged up the slope of San Juan Hill. I owe you men. . . . If New Mexico wants to be a state, I will go down to Washington to speak for her and do anything I can.”

Roosevelt was a staunch proponent for Oklahoma, Arizona, and New Mexico’s statehood status while he was President. He even made it part of the Republican Party platform in 1900.

A Commemorative Stamp

Rough Riders 1948

In 1948, the 50th anniversary of Roosevelt’s Rough Riders, a commemorative US postage stamp was released in the memory and honor of the unit. The stamp depicted Captain William Owen O’Neill, nicknamed ‘Bucky’, who fell while leading troop A during the Battle of San Juan Hill. The Rough Riders would have annual reunions until 1967, with the location being Las Vegas. At the last reunion, Jesse Langdon was the only veteran to attend. He passed away in 1975.


While people may have differing opinions about the Spanish-American war and the role of the United States in international matters, the fact remains that Roosevelt’s Rough Riders are a definite influence on American history and even its culture. Roosevelt himself was impressed by the valor and sacrifices of the men in this unit. Since one of his hobbies was writing, we can still look up his speeches on the Rough Riders and their contributions. The unit was indeed a unique one, and should not be forgotten anytime soon.