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Teddy Roosevelt and the Rough Riders at Kettle Hill
by Scott Mingus, Jr.
In the year 1898, tensions between the countries of Spain and the United States were very high, more so than at any other time in the two nations' past. Spain's control of the island of Cuba, just off the Florida coastline, was putting a deepening strain on their relationship with Washington. Cuban rebels were in a bitter fight against Spanish forces as they tried to gain control of Cuba, freeing the island from what they saw as a colonial master. In order to protect American lives and property in Cuba, Congress sent a fleet of warships to the harbors in and surrounding Cuba. One of the battleships, the U.S.S. Maine, was floating in the harbor of Havana on the night of February fifteenth. Around nine-forty that night after a routine day, a very large explosion ripped through the hull of the ship. Sinking within fifteen minutes, only ninety men of the three hundred and fifty sailors on board were able to escape.(1)

News of the sinking of the Maine rapidly spread throughout the United States. An official Navy inquiry came to the controversial conclusion that a submarine mine must have caused the explosion that doomed the now-famous ship, ignoring or discounting other evidence that suggested less sinister reasons for the loss of the battleship. The American press soon pinpointed the blame for the mine directly on Spain. Public outrage began to increase as the phrase, "Remember the Maine!, became a popular rallying cry for all those demanding immediate action.(2)

At the time of the sinking of the Maine, Theodore Roosevelt was the assistant Secretary of the Navy in Washington. Already an advocate of war with Spain, Roosevelt began a public campaign to promote war efforts, and to rally the American people to his political views. While personally promoting these war efforts, Roosevelt began to prepare the Navy for an upcoming war with Spain. Influenced by the growing public outrage and by other pro-war politicians, U. S. President William McKinley on April 24, 1898 declared war on Spain. Believing so strongly in the intervention cause, Roosevelt resigned from his political post and joined the military to advance his personal views.

"The President and my own Chief Secretary Long were very firm against my going, but they said that if I was bent upon going that they would help me."(3) Roosevelt stated, longing to be named a senior general. However because of his lack of previous military service and any real knowledge of combat strategy, Roosevelt was merely appointed to a lieutenant colonel position beneath life-long friend Colonel Leonard Wood in the newly-formed 1st United States Volunteer Cavalry. These first volunteers were part of a group of three regiments that were being assembled in the Western states for duty against the Spanish. After receiving notice of his post, Roosevelt was asked by his superior to begin the task of recruiting members for the regiment in the San Antonio, Texas area, as well as other key cities throughout the West. His task was relatively easy as many volunteers began to come forward to the recruiting stations (often hotel bars and saloons). Response was so great that Roosevelt and Wood had to turn away many applicants as the enrollment lists rapidly were filled. A fever of patriotism spurred many to joining the new cavalry regiment. In some cases, relief from boredom was the main reason for enlistment…"Some had come for the war, others had signed up looking for an adventure."(4)

Volunteers from different backgrounds throughout the nation were assigned to the regiment. Educated men from Ivy League schools, Western gunfighters, former lawmen, Native Americans, outlaws, farmers, shopkeepers, Mexican-Americans, and many other classes of men came together to form the soldiers of this regiment. With this diverse collection of colorful characters, "the public promptly christened us the "Rough Riders."(5) This nickname given to the 1st US Cavalry Volunteer Cavalry Regiment is still remembered today and will follow them throughout history.

Following the recruiting of the regiment, Roosevelt and Wood set up drills and basic training in a San Antonio camp. Both officers knew that their chances of seeing any real action in the upcoming war depended on how fast the troops could become field-ready, as they correctly believed that the war would be short and violent. They also had a daunting task of trying to build a solid command formation from the base up, strictly with volunteers many of whom had no previous formal military training or experience. With "Colonel Wood's experience and organizing ability, Lieutenant Colonel Roosevelt's political contacts and enthusiasm in procuring equipment and Major Brodie's regular army background the Rough Riders had many advantages."(6)  High enthusiasm, morale, and the willingness to learn made the training of the troops easier for Wood and Roosevelt.

Training in San Antonio went extremely well and on May 28th, 1898, orders came for the Rough Riders to move out for Tampa Bay, Florida. Riding railway cars through the heartland of the old Confederacy was an unexpectedly pleasant experience for the green, but enthusiastic Rough Riders. "At every stop from Texas to Florida large crowds waited to greet the Rough Riders."(7) Many of them did not think that they as blue-uniformed soldiers would receive such a warm and hearty greeting in the Deep South so soon following the bitter Civil War.

Arriving in Tampa on June 1st, the Rough Riders began another series of training exercises while waiting for further orders. Then on the 6th, the final orders came through from headquarters for the Rough Riders to assemble and begin preparations for their departure to Cuba and to war. They were to be a part of an invasion force made up of 17,000 Federal troops. Due to poor planning on behalf of headquarters, the Rough Riders were only to take two-thirds of their original force, leave the horses, pack trains, and support troops behind. They even had to commandeer a train in order to beat another regiment to the harbor to preserve a spot on the transport ships.

As the train pulled into the harbor, the Rough Riders were fondly singing "Rough, tough, we're the stuff. We want to fight and can't get enough."(8) Roosevelt was given the chance to command the loading of the troops into the transports. Everything went well and the troops were in high spirits. Delayed from sailing for a full week due to an unfounded rumor of a modern-day Spanish armada being off the coast of Key West, the transports filled with troopers finally set off for Cuba on June 13th.

In order for the troopers to make a safe landing on Cuba, the Navy was engaged in bombing the Spanish and Cubans at the drop-off point of Daiquiri. The troopers once again had to wait in order to see any action. "On the morning of June 22nd the welcome order for landing came."(9) But the task of unloading the troops began to take a toll on Roosevelt as he saw the methods of other commanders being so highly informal. "We did the landing as we had done everything else- that is, in a scramble, each commander shifting for himself."(10) Some troopers in other regiments lost their lives by being caught up in the current. Roosevelt sent a small detachment ahead of the main departure group in order to raise the Rough Rider flag over the town as a sign of encouragement to the rest of the regiment as they disembarked.

By that afternoon, all of Wood's men were successfully on the shores of Cuba and were preparing for their first combat action. Much to their surprise, no formal resistance to their landing had came from Spanish forces, and there were still no signs of any enemy activity. Roosevelt was personally disappointed, as his dreams of using military reputation to advance his political aims appeared to be dashed. Little did the young politician-turned-soldier know that he was about to step into his first real test of military leadership. On the morning of June 24th, the Rough Riders departed Daiquiri through a narrow steep trail on top of a long ridge, and headed towards the sleepy town of Los Guasimas. Their objective was to arrive at Las Guasimas at the same time as General Young's column that was to arrive from a less steep trail. The troopers began to break out in their favorite song "There'll be a Hot Time in the Old Town Tonight."(11)

Colonel Wood stopped the singing and then ordered the men to be silent. Scouts from L Company had just reported that an enemy outpost had been located. Wood quickly ordered Roosevelt to deploy the troops and locate the Spanish. As Captain William "Bucky" O'Neill's troops were deploying into a skirmish line upon the right flank, suddenly the Spanish soldiers opened fire. Hidden within heavy brush and with their ability to blend in with the surroundings, the Spanish troops were a difficult target to hit. "But they themselves were entirely invisible. The jungle covered everything, and not the faintest trace of smoke was to be seen in any direction to indicate from whence the bullets came."(12)

As the Arizona brigade under O'Neill worked their way through the thick underbrush, the Spanish fire began to take effect on them. A couple of troopers were hit and fell screaming, and the constant stream of bullets pinned down the rest of the brigade. It was not until reinforcements came up the ravine that O'Neill's brigade was able to advance into the open terrain. The sight of the advancing Arizona brigade and the bringing up of fresh reinforcements caused a retreat of the Spanish troops, as the full force of the Americans became more visible. Troopers on the left flank, including Wood's regiment, were having their own difficulties. The new wave of Spanish retreating from the fight on the right flank suddenly joined into the fight against the Rough Riders. A detachment of Rough Riders came under very heavy fire and they suffered several causalities. Roosevelt, seeing this detachment being held at bay by the Spanish, took it upon himself to order a rescue attempt. Troops under Captain Allyn Capron obeyed Roosevelt's first combat order and were able to rescue the pinned detachment despite suffering heavy losses themselves as they advanced.

Following the successful relief mission, Roosevelt and brigade commander General Alexander Brodie conferred and decided to attack a line of Spanish entrenchment near a fortified house. Unable to locate Colonel Wood to ask for his formal permission to attack, Roosevelt decided to personally take command of G troop for a short time. Fearlessly leading this assault, Roosevelt and the detachment of Rough Riders were able to push the Spanish away from the entrenchments and the house. Roosevelt had succeeded in his first actual military attack. The defeated Spanish retired to the San Juan Heights guarding the important city of Santiago.

Colonel Wood, who finally arrived at the now secured entrenchment, surveyed the field, filling with enemy casualties and the tired Rough Riders, exhausted from the energy expended in the heat through their climb up the steep trail and the subsequent combat. "With his exhausted Rough Riders in possession of the Spanish entrenchments, Wood considered his men to be incapable of further pursuit and decided to camp there and wait for orders."(13) The Rough Riders had won their first action in the skirmish at Las Guasimas.

New orders arrived a couple of days later on July 1st for the Rough Riders to deploy along the bottom of the San Juan Heights to help in a campaign to displace the Spanish stronghold on top of the hills. The Spanish defensive line was about a mile long and was armed with many gun emplacements. Taking their assigned positions below the heights, the U.S. troopers waited for the signal for advance on the Spanish. The Rough Riders were to deploy below Kettle Hill while the rest of the First Infantry Division was to make the main offensive on San Juan Hill. At seven in the morning, American long-range guns opened the battle. The troopers soon found themselves under a steady stream of Spanish bullets, and for about an hour they had to endure the firing under their exposed positions. After an hour of the firing a tragic blow was dealt to the Rough Riders. Captain "Bucky" O'Neill was killed while trying to calm and steady his troops. The entire regiment keenly felt his sudden death, and if it was not for the quick thinking of commanders surrounding O'Neill's men, their attack might have not gone forward.

Around noon, the First Infantry Division began their assault on San Juan Hill with the support of General Joseph Wheeler's Cavalry. Seeing the attack on adjacent San Juan Hill starting, Roosevelt still in position in reserve below Kettle Hill became more and more impatient. Finally he was given the command to start the Rough Riders' assault up Kettle Hill. Roosevelt, feeling very excited, began to ride up and down the line urging the men forward. Seeing Roosevelt personally urging them forward, momentum quickly spread and finally the entire regiment was on the move forward, passing the forward lines of other American units. As the Rough Riders arrived at the forward positions of the First and Ninth Cavalry (who had not received their own orders to advance), Roosevelt took the initiative and quickly invited them to join in the advance up the hill. With no orders from their superiors, the two groups initially declined the offer until the sight of the grinning Rough Riders rushing passed became too much, and they too joined the fight against the Kettle Hill defenders.

As the American cavalry and infantry reached the lower slopes of the hill, Spanish fire became more deadly and more accurate. In addition to dealing with the annoying enemy fire, the Rough Riders also encountered two barbed wire fences on the slopes. But the fences and the bullets could not stop the advance as the Rough Riders and their supports continued to steadily climb the hill. As the Americans reached the second fenceline, it became apparent to the Spanish defenders that to avoid hand-to-hand combat, they must withdraw. "The Spaniards, ordered to avoid a hand-to-hand fight, clung to their positions until the line of advancing cavalrymen swarmed over the second fence and then they began to withdraw."(14)

Reaching the top of the hill, the Rough Riders established some initial defensive measures to secure the area as the Spanish on the higher San Juan Hill began to fire upon them. Seeing that the attack on the adjacent height was not going too well as heavy fire and other obstacles were stopping the forward progress, Roosevelt himself decided to lead a charge, a decision reinforced when three Gatling guns got to the top of Kettle Hill to support an attack.

"Shouting for his men to follow, he jumped over a barbed wire fence and ran down the slope."(15)  Roosevelt ran about one hundred yards when he turned around to notice that only five of his troopers had followed him down the slope into the swale between Kettle and San Juan Hills. Roosevelt turned around and returned to the crest of Kettle Hill where his troopers claimed they did not hear his order to charge. Forming them quickly into an assault line, Roosevelt again ordered the charge. This time, the entire regiment with support from other nearby forces went forward towards San Juan Hill. The First Infantry Division, halted in place along that hill's slopes, began to press harder up the incline as they saw Roosevelt's troopers coming to help them. By two thirty in the afternoon, the entire heights were possession of the American troops. With the victory at San Juan Heights, the Americans were able to move into the city of Santiago and establish a good offensive position to fire on the Spanish fleet in the harbor. With the subsequent destruction of the Spanish fleet from an attack from Rear Admiral William T. Sampson, the Americans were able to win the battle, and force and early end to the war.(16)

Theodore Roosevelt's personal actions at the battle of San Juan Heights would win him the nation's highest military honor, the Congressional Medal of Honor. His actions within the entire war from the early days of recruiting and training through to his personal courage under fire would win him respect with many of his senior officers. His enthusiasm, confidence, bravery, and high regard for his troopers would him enduring fame with his Rough Riders, who associated victory solely with Roosevelt, not with their actual commander Leonard Wood, who has all but been forgotten by history.

(1). Herner, Charles. The Arizona Rough Riders. Tucson: The University of Arizona Press, 1970. Pg. 2.
(2). Athearn, Robert G. American Heritage New Illustrated History of the United States: Volume 12 A World Power. New York: Fawcett Publications, Inc., 1971. Pg. 1005.
(3). Roosevelt, Theodore. The Rough Riders. New York: Charles Scribner’s Sons, 1923. Pg. 5.
(4). Ibid. Pg. 6.
(5). Ibid. Pg. 7.
(6). Herner, Charles. The Arizona Rough Riders. Tucson: The University of Arizona Press, 1970. Pg. 39.
(7). Ibid. Pg. 72.
(8). Ibid. Pg. 84.
(9). Roosevelt, Theodore. The Rough Riders. New York: Charles Scribner’s Sons, 1923. Pg 70.
(10). Morehead, Albert. The New American Webster Handy College Dictionary. New York: Penguin Group Book, 1995. Pg. 1008.
(11). Herner, Charles. The Arizona Rough Riders. Tucson: The University of Arizona Press, 1970. Pg. 104.
(12). Roosevelt, Theodore. The Rough Riders. New York: Charles Scribner’s Sons, 1923. Pg. 89.
(13). Herner, Charles. The Arizona Rough Riders. Tucson: The University of Arizona Press, 1970. Pg. 113.
(14). Ibid. Pg.140.
(15). Ibid. Pg. 145.
(16). Athearn, Robert G. American Heritage New Illustrated History of the United States: Volume 12 A World Power. New York: Fawcett Publications, Inc., 1971. Pg. 1009.
Teddy Roosevelt and the Rough Riders at Kettle Hill by Scott Mingus, Jr.
Copyright © 2003 Scott Mingus, Jr.