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Among Theodore Roosevelt's many accomplishments were two terms as President of the United States, the publishing of more than forty works of nonfiction, the exploration of the South American wilderness, and having his likeness sculpted on Mount Rushmore. However, even with all of these and many other achievements, Theodore "Teddy" Roosevelt often stated that participating in the Battle of San Juan Hill, Cuba, during the Spanish-American War was one of his proudest moments. Roosevelt's service with the First U.S. Volunteer Cavalry Regiment, also known as the "Rough Riders," lasted only four months, but he proclaimed "there are no four months of my life to which I look back with more pride and satisfaction."(1) To most people, the charge up San Juan Hill is one of the two most memorable events connected with the "Splendid Little War."(2) The other is the sinking of the USS Maine, which helped set the stage for war.
The American victory over Spain placed the nation among the world's great powers. For Roosevelt, the Spanish-American War fulfilled a lifelong dream. While friends in the newspaper business ensured that his exploits in Cuba were not overlooked by the public, the future President yearned for even greater acclaim. He coveted the country's highest military decoration, the Medal of Honor. Despite an intense lobbying effort by some of his superior officers and a close friend, Senator Henry Cabot Lodge, Roosevelt's request for the medal was denied by the War Department. Questions remain as to whether Roosevelt was refused the Medal of Honor because he was undeserving or if friction between himself and the War Department was the actual reason for denial.
Most of the volunteers under the first call came from existing state militia or national guard outfits since they numbered about 125,000 men. The order for troops also permitted the federal government to raise three volunteer cavalry regiments to serve independently from the state units.(8) Secretary of War Alger knew the perfect candidate to command the first regiment: Theodore Roosevelt. Upon learning from Alger that the First United States Volunteer Cavalry Regiment was his to command, Roosevelt was ecstatic. He declined the offer, however, since his only military service had been three years in the New York National Guard, and he felt this was not enough experience to lead an entire regiment during wartime. As a compromise, Roosevelt suggested that he serve as lieutenant colonel if his good friend Leonard Wood was named as the commander. Alger agreed, and the Rough Riders were born.(9)
Wood was an ideal choice to command the newly formed regiment. He had many of the same political connections as Roosevelt, whom he had met in mid-1897 while serving as the White House physician, and they developed a deep friendship. Besides a career as a medical officer, Wood had served as both an army assistant surgeon and line officer during the expedition against Geronimo in 1886. He distinguished himself in the campaign and received the Medal of Honor in March 1898 for his role in Geronimo's surrender. Wood was the only officer serving in the long campaign to receive the award, and rumors circulated that his political ties were the reason he had been singled out.(10)
The Rough Riders trained in San Antonio, Texas, for about four weeks, then joined the other outfits congregating in Tampa, Florida, for transport to Cuba.(15) The expedition was organized as the U.S. Army's Fifth Corps. They were led by the rotund Maj. Gen. William R. Shafter, a Medal of Honor recipient during the Civil War and veteran of the Indian wars. The Rough Riders had the distinction of being one of only three volunteer regiments that initially went to Cuba.(16)
Shafter's plan to assault the San Juan Heights, based upon reconnaissance by his own troops and the Cuban army, was to send the Fifth Corps through the only two practicable routes in the jungle-covered terrain. The First Infantry Division under Brig. Gen. Jacob F. Kent and Wheeler's cavalry would approach Kettle and San Juan Hills through the same road the army had followed from Siboney. The first phase of the attack was for Brig. Gen. Henry W. Lawton's Second Infantry Division to take the village of El Caney on the right flank by way of the road to Guantanamo, which he claimed was possible in two hours. Lawton was then to move on to Santiago with Kent and Wheeler approaching to his left. If the plan went as designed, the three divisions would clear the Spaniards from the San Juan Heights and bring Santiago under siege.
The troops on Kettle Hill under the orders of Sumner and the inspiration of Theodore Roosevelt started down the west slope of the hill and up the northern extension of San Juan Hill. The cavalry encountered trenches filled with dead Spaniards or those who wished to surrender. Some of the bolder enemy were shot in full flight by the Rough Riders and other regiments now firmly in place on San Juan Hill. The assaults against Kettle and San Juan Hills were against Spanish troops that had already begun pulling back. Around noon their two field artillery pieces had been depleted of ammunition, and their infantry had been decimated by the Gatling gun, artillery, and rifle fire. Those who remained in the trenches when the U.S. cavalry appeared were either dead or wounded. The Rough Riders did charge San Juan Hill, but only after the assault on the more strategically important Kettle Hill.
The Spaniards were not the only ones suffering from disease. By the end of July, almost 20 percent of Shafter's men were hospitalized because of yellow fever, dysentery, and a large number of malaria cases. At first the War Department felt the Fifth Corps should remain in Cuba and wait out the epidemics, but Shafter warned that the disease would worsen unless the sick men were returned to the United States. Shafter solicited the views of his division and brigade commanders, and they concurred that the weakened soldiers must leave Cuba immediately or risk yellow fever deaths rising by the hundreds. All three of Shafter's division commanders and several of the brigade officers, including Roosevelt, drafted and signed a letter stating their views on the withdrawal from Cuba. The letter was included with Shafter's dispatch and sent to the War Department on August 3. Roosevelt also took matters into his own hands and sent an urgent plea to his friend, Senator Henry Cabot Lodge. A copy of Shafter's dispatch was leaked to an Associated Press correspondent at the Fifth Corps headquarters, and the generals' letter was printed in newspapers across the United States. Although the exact source of who leaked the dispatch was never revealed, Roosevelt has often been considered the prime suspect. Because the dispatch went through so many hands, it was called the "Round Robin" letter.
Before Roosevelt and his Rough Riders left Cuba for the United States, he commenced fighting another, personal, battle. General Wheeler promised to recommend him to the War Department for a Medal of Honor, and his good friend Leonard Wood got the ball rolling by submitting the first endorsement on July 6. In a letter to the War Department Adjutant General's office in Washington, Wood plainly stated that "I have the honor to recommend Lieut. Col. Theodore Roosevelt . . . for a Medal of Honor for distinguished gallantry in leading a charge on one of the entrenched hills to the east of the Spanish position in the suburbs of Santiago de Cuba, July First, 1898."(31)
Although a nice gesture, Wood's recommendation had very little merit. He had not been present during the actual charge, and Wood's enemies asserted that he had got lost in the woods trying to maneuver his brigade, reaching San Juan Hill only after the fighting had ended. He was therefore not a reliable witness, and the War Department would later reveal this fact. Following Wood's recommendation were similar endorsements from Generals Wheeler and Shafter. Like Wood, they also had not witnessed Roosevelt's alleged heroic charge.
Roosevelt also pushed the Medal of Honor issue to his long-time companion, Massachusetts Senator Henry Cabot Lodge. Roosevelt boasted to him "that General Wheeler intends to recommend me for the Medal of Honor; naturally I should like to have it." In a another letter to Lodge complaining about the deplorable conditions in Cuba and the deaths that might result from the malaria, Roosevelt reflected upon his own possible death. He told Lodge that "if I do go, I do wish you would get that medal for me anyhow, as I should awfully like the children to have it, and I think I earned it."(32)
Although Roosevelt may have deemed Meikeljohn's response a snub, his application was indeed one of many pouring into the War Department. Joining him on the Medal of Honor and Brevet list were more than fifty other veterans of the Spanish-American War. In order to deal with each case in a fair manner, Secretary of War Alger established on November 9, 1898, a "board of officers . . . for the purpose of making recommendations for brevet promotions, the awards of medals of honor, and certificates of merit for the officers, and enlisted men who participated in the campaigns of Santiago, the Philippines, and Porto Rico."(34)
He prepared himself for possible denial after learning from Senator Lodge that Secretary Alger had told him at a White House dinner that the Rough Rider would not receive the medal. Roosevelt also claimed that Alger had made this announcement to others on a number of occasions. He wrote to Leonard Wood and told him "pray do not think of the medal anymore. There is nothing to be done about it. I really care more for the recommendations for it than the medal itself."(37) In a letter to Gen. Francis Vinton Greene, Roosevelt vented his frustrations about Alger: "You will readily understand however, that both my friends and myself feel that when the Secretary announces in advance publicly and repeatedly that the medal must not and will not be given, this mere fact itself amounts to coercion of the Board, and I shall think that the Board might better sensitiveness about the coercion than about my friends having called in consequence of the Secretary's public statements."(38)
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