The Rough Riders was a nickname given to the 1st United States Volunteer Cavalry, one of three such regiments raised in 1898 for the Spanish–American War and the only one to see combat. 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 , 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. The U.S. had gone to war in opposition to Spanish colonial policies in Cuba, which was then torn by a rebellion.Paul Mathingham Hutton, "T.R. takes charge", American History 33.n3 (August 1998), 30(11). The regiment was also nicknamed "Wood's Weary Walkers" for its first commander, Colonel Leonard Wood. This reflected their dissatisfaction that despite being cavalry, they ended up fighting in Cuba as light infantry, since their horses were not sent there with them.

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. When Wood was promoted to become commander of the 2nd Cavalry Brigade, the regiment became known as "Roosevelt's Rough Riders". That term was borrowed from Buffalo Bill, who called his traveling Western show "Buffalo Bill's Wild West and Congress of Rough Riders of the World."

The original plan called for the regiment to be composed of frontiersmen from the Indian Territory, the New Mexico Territory, the Arizona Territory, and the Oklahoma Territory. However, after Roosevelt joined the ranks, it attracted an odd mixture of Ivy League athletes, glee club singers, Texas Rangers, and Native Americans. All accepted into the regiment had to be skilled horsemen and eager to see combat. 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.

Early history Formation

The volunteers were gathered in four areas: Arizona, New Mexico, Oklahoma, and Texas. They were gathered mainly from the southwest because the hot climate region that the men were used to was similar to that of Cuba where they would be fighting. "The difficulty in organizing was not in selecting, but in rejecting men." The allowed limit set for the volunteer cavalry men was promptly met. With news trickling down of Spanish aggression and the sinking of the USS Maine, men flocked from every corner of the regions to display their patriotism. 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. Half the unit would come from New Mexico according to Roosevelt. Among these men were also police officers and military veterans who wished to see action again, most of whom had already retired. Thirty years removed from any armed conflict, men who had served in the regular army during campaigns against Native Americans or during the Civil War sought out to serve as higher-ranking officers, since they already had the knowledge and experience to lead and train the men. The unit thus would not be without experience. Leonard Wood, an Army doctor who served as the medical adviser for both the President and Secretary of War, was appointed colonel of The Rough Riders, with Roosevelt serving as lieutenant colonel.David S. Pierson, "What the Rough Riders lacked in military discipline, they made up for with patriotic fervor and courage" Military History, XV (June 1899), 10. One particularly famous spot where volunteers were gathered was in San Antonio, Texas, at the Menger Hotel Bar. The bar is still open and serves as a tribute to the Rough Riders, containing much of their and Theodore Roosevelt's uniforms and memories.

Equipment 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. The Rough Riders were armed with Model 1896 Carbines in caliber .30 US (i.e., .30-40 Krag). "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." The Rough Riders also used Bowie knives. A last-minute gift from a wealthy donor were a pair of modern tripod mounted, gas-operated M1895 Colt–Browning machine guns in 7mm Mauser caliber.

In contrast, the uniforms of the regiment were designed to set the unit apart: "The Rough Rider uniform was a slouch hat, blue flannel shirt, brown trousers, leggings, and boots, with handkerchiefs knotted loosely around their necks. They looked exactly as a body of cowboy cavalry should look." This "rough and tumble" appearance contributed to earning them the title of "The Rough Riders."

Training Training was very standard, even for a cavalry unit. They worked on basic military drills, protocol, and habits involving conduct, obedience, and etiquette to improve their overall physique and mental status. The men proved eager to learn what was necessary and the training went smoothly. It was decided that the men would not be trained to use the saber as cavalry often did, as they had no experience with it. Instead, they used their carbines and revolvers as primary and secondary weapons. Although the men, for the most part, were already experienced horsemen, the officers refined their techniques in riding, shooting from horseback, and practicing in formations and in skirmishes. Along with these practices, the high-ranking men heavily studied books filled with tactics and drills to better themselves in leading the others. During times which physical drills could not be run, either because of confinement on board the train, ship, or during times where space was inadequate, there were some books that were read further as to leave no time wasted in preparation for war. The competent training that the volunteer men received prepared them best as possible for their duty. 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. Of the 1,832 deaths attributed to disease, 1,590 were specifically caused by typhoid fever. Notably, a significant portion of these fatalities occurred at training sites in the southeastern United States.

Spanish–American War

Departure from the United States On May 29, 1898, 1,060 Rough Riders and 1,258 of their horses and mules made their way to the Southern Pacific railroad to travel to Tampa, Florida, where they would set off for Cuba. The lot awaited orders for departure from Major General William Rufus Shafter. Under heavy prompting from Washington D.C., General Shafter gave the order to dispatch the troops early before sufficient traveling storage was available. Due to this problem, only eight of the 12 companies of The Rough Riders were permitted to leave Tampa to engage in the war, and many of the horses and mules were left behind. Aside from Lieutenant-Colonel Roosevelt's first-hand mention of deep, heartfelt sorrow from the men left behind, this situation resulted in a premature weakening of the men. Approximately one-fourth of them who received training had already been lost, most dying of malaria and yellow fever. This sent the remaining troops into Cuba with a significant loss in men and morale.Hutton, "T.R. takes charge," 30(11).

Upon arrival on Cuban shores on June 23, 1898, the men promptly unloaded themselves and the small amount of equipment they carried with them. Camp was set up nearby and the men were to remain there until further orders had been given to advance. Further supplies were unloaded from the ships over the next day including the very few horses that were allowed on the journey. "The great shortcoming throughout the campaign was the utterly inadequate transportation. If they had been allowed to take our mule-train, they could have kept the whole cavalry division supplied," Roosevelt later wrote. Each man was only able to carry a few days worth of food which had to last them longer and fuel their bodies for rigorous tasks. Even after only 75 percent of the total number of cavalrymen was allowed to embark into Cuba, they were still without most of the horses they had so heavily been trained and accustomed to using. They were not trained as infantry and were not conditioned to doing heavy marching, especially long-distance in hot, humid, and dense jungle conditions. This ultimately served as a severe disadvantage to the men who had yet to see combat.

Battle of Las Guasimas

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. Upon arrival at their relative destination, the men slept through the night in a crude encampment nearby the Spanish outpost they would attack early the next morning.Pierson, "What the Rough Riders lacked ...," 10. The American side included the 1st U.S. Volunteer Cavalry, under Leonard Wood, the 1st U.S. Regular Cavalry, and the 10th U.S. Regular Cavalry (this consisted of Afro-American soldiers, then called Buffalo soldiers). Supported by artillery, the American forces numbered 964 men,Wheeler, J., 1899, The Santiago Campaign in Campaigns of Wheeler and His Cavalry, Atlanta: Hudgins Publishing Company supported by 800 men from Castillo.

The Spanish held an advantage over the Americans by knowing their way through the complicated trails in the area of combat. They predicted where the Americans would be traveling on foot and exactly what positions to fire on. They also were able to utilize the land and cover in such a way that they were difficult to spot. Along with this, their guns used smokeless powder which did not give away their immediate position upon firing as other gunpowders would have. This increased the difficulty of finding the opposition for the U.S. soldiers. In some locations, the jungle was too thick to see very far. 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. Continuing to advance, the Rough Riders eventually forced the Spanish to withdraw completely from their final positions. Rough Riders from A Troop on the far-right linked up with their regular counterparts and helped them seize the Spanish positions on the long finger-like hill to the right of the right road, with both Rough Riders and Regulars meeting at the base of the hill. By this time it was approximately 9:30 a.m. Reinforcements from the regular 9th Cavalry arrived 30 minutes after the fight.Roosevelt, Theodore, The Rough Riders Chapter III, page 18, Bartleby Website