Prologue Magazine
Spring 1998, Vol. 30, No. 1

"I Am Entitled to the Medal of Honor and I Want It"
Theodore Roosevelt and His Quest for Glory, Part 2


Leaving Tampa on June 6, the Fifth Corps anchored a week later off the coast of Santiago de Cuba and remained there until an advance force of the U.S. Army landed at the small port of Daiquiri, seventeen miles from Santiago. With the help of naval gunfire and a small force of Cuban revolutionaries under the command of Gen. Calixto Garcia, the three hundred Spanish troops in the area of Daiquiri were forced to withdraw on June 22. Because of heavy surf conditions, Shafter selected a landing point eight miles closer to Santiago at the port of Siboney. By June 26, most of the expedition was on shore, but not without casualties. Two men and a number of artillery horses and pack mules drowned in the rough sea. Roosevelt remembered that "we did the landing as we had everything else--that is, in a scramble."(17)
Landing at Daiquiri Landing at Daiquiri. (NARA 111-SC-94528)

Upon landing in Cuba, the mission of the Fifth Corps was unclear. The War Department gave Shafter instructions to destroy the Spanish forces at Santiago, and how to go about this was left up to him. As soon as a sufficient force landed on shore at Siboney, Shafter ordered the march toward Santiago. Although the Spaniards put up no resistance to the American landings, Cubans in the area reported that a force of two thousand Spaniards were about four miles from Siboney in the village of Las Guasimas. Former Confederate officer Maj. Gen. "Fighting" Joe Wheeler, who commanded the Fifth Corps cavalry division as a volunteer, sent Brig. Gen. Samuel B.M. Young on a reconnaissance toward the village with his brigade, which included the Rough Riders and the African American Tenth U.S. Cavalry. After a two-hour fight, Young's brigade had the enemy fleeing toward Santiago.(18)

Sixteen Americans and ten Spaniards were killed in the fight. Figuring prominently in the skirmish were the Rough Riders, who suffered eight casualties. Newspapers across the United States proclaimed it a Rough Riders victory. Most responsible for the accolades was correspondent Richard Harding Davis, who tagged along with the Rough Riders and acted as Roosevelt's own press secretary. In reality, Wheeler had advanced the cavalry prematurely, and they had been ambushed. Two of the Rough Riders killed were among the regiment's more promising troopers, Capt. Allyn K. Capron and Sgt. Hamilton Fish. The most positive aspect of the skirmish was that it boosted morale among the soldiers and gave them confidence for the big fight that lay ahead.(19)

After the unexpected Las Guasimas fight, Shafter decided against any further advances until he could build up substantial supplies at Siboney and Daiquiri. On June 28 Shafter learned that a Spanish relief force was heading to reinforce troops entrenched among the heights surrounding Santiago. Two days later he ordered his forces to be ready to march toward Santiago on July 1. The ultimate goal was San Juan Hill, which was also known as either San Juan Heights or San Juan Ridge.(20)

The San Juan Heights rise above Santiago, about two miles east of the city. A small rise known as Kettle Hill was named for an abandoned mill and its iron kettles used to refine sugar. San Juan Hill rises to the southwest, about 400 yards further than Kettle Hill, and stands about 125 feet high with a brick blockhouse at the summit. Just east of Kettle and San Juan Hills flows the San Juan River. Approximately a thousand yards west of the San Juan Heights there was a strong line of Spanish fortifications that included barbed-wire entanglements, rifle pits, and trenches dug on the heights and to their rear.

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 Battle of Santiago began early in the morning of July 1 with Lawton attacking El Caney, but his force of sixty-six hundred men met heavy resistance from the five hundred Spaniards garrisoned at the village. Not until late afternoon did El Caney come under American control.

With Lawton bogged down in El Caney, the First Cavalry Division and First Infantry Division with about eight thousand men would have to attack the defenses of San Juan Heights without the planned infantry support. The cavalry was now under the command of Brig. Gen. Samuel S. Sumner, who temporarily replaced an ill General Wheeler. As result of Wheeler's illness, Wood was promoted to brigadier general, and Roosevelt was raised to the rank of colonel of the Rough Riders.

The infantry division under General Kent moved behind the Sumner's cavalry division along the road leading to the heights at about 11 a.m. Gradually the infantry pressed up alongside the cavalry, then both divisions took position in an area that provided little cover, with the cavalry on the right and the infantry on the left. Not yet having received orders from Shafter's headquarters, the men were exposed in the open with no clear course of action. Before the men completed their deployment, the Spanish troops on San Juan and Kettle Hills commenced rifle and artillery fire.

What triggered the Spanish fusillade was an observation balloon operated by the Signal Corps. Their mission was to obtain more intelligence about the Spanish position, but the balloon gave the Spaniards a perfect marker on which to aim their fire. How many American casualties the balloon caused is impossible to say. On the positive side, the two observers aboard the balloon gathered information on the enemy's strength at San Juan Hill and discovered an alternate trail that helped spread the deployment of the Fifth Corps infantry.(21)

Sumner and Kent realized that San Juan Hill was heavily defended and the infantry and cavalry would be decimated unless they either advanced or retreated. Kent's infantry, followed by Sumner's cavalry, deployed along a narrow path, and by 1 p.m. the Americans established a firing line facing the heights against the Spanish right flank. Lt. John H. Parker and his battery of Gatling guns caused the most destruction. At a range of six hundred to eight hundred yards, Parker demoralized the Spaniards by firing continuously for little over eight minutes.(22)

Using Parker's guns as a cover, the cavalry and infantry finally received permission to attack the Spanish forward positions along San Juan Heights. What actually happened at this point is still quite confusing. A number of different versions of the battle by its participants conflict with each other. Of particular interest to this study is Roosevelt's own account of the events. In his two reports to Leonard Wood that were published in the Report of the Secretary of War, as well as his postwar story in The Rough Riders, Roosevelt gives the impression that he alone was the first to charge the San Juan Heights to drive away the entrenched Spaniards. This image of Theodore Roosevelt was propagated with the help of Richard Harding Davis. Reporting for the New York Herald, Davis transcribed what Roosevelt told him, then added his own twist to the story. In addition to the newspaper articles, magazines and books picked up his story. Davis depicted a fearless Roosevelt, wearing a blue polka-dotted bandanna, charging up the hill mounted on his horse, Texas. Thus the legend of Theodore Roosevelt was created.(23)

Theodore Roosevelt and Rough Riders at San Juan Hill Roosevelt and his Rough Riders atop San Juan Hill. (NARA 306-ST-505-58-4822)

The first report, written on July 4, 1898, provides Roosevelt's initial claim for credit in charging the heights. He wrote,

After crossing the river at the ford we were moved along and up its right bank under fire, and were held in reserve at a sunken road. . . . We then received your order to advance and support the regular cavalry in the attack on the entrenchments and blockhouses on the hills to the left. The regiment was deployed on both sides of the road, and moved forward until we came to the rearmost lines of the regulars. We moved forward until I ordered a charge, and the men rushed the blockhouse and rifle pits on the hill to the right of our advance. They did the work in fine shape, though suffering severely. The guidons of Troop E and G were first planted on the summit, though the first men up were some A and B troopers, who were with me.

After the passage of almost three weeks, Roosevelt's final report to Wood elaborated even further on his immortal charge.

We moved through several skirmish lines of the regiment ahead of us, as it seemed to me that our only chance was in rushing the entrenchments in front. . . . Accordingly we charged the blockhouse and entrenchments on the hill to our right against a heavy fire. It was taken in good style, the men of my regiment thus being the first to capture any fortified position and to break through the Spanish lines. The guidons of G and E troops were first at this point, but some of the men of A and B troops who were with me personally got in ahead of them. At the last wire fence up this hill I was obliged to abandon my horse and after that went on foot. . . . By the time San Juan was taken a large force had assembled on the hill we had previously captured, consisting not only of my own regiment but of the ninth and of portions of other cavalry regiments.(24)

Theodore Roosevelt and the Medal of Honor, Part 1
Theodore Roosevelt and the Medal of Honor, Part 3
Theodore Roosevelt and the Medal of Honor, Part 4

Articles published in Prologue do not necessarily represent the views of NARA or of any other agency of the United States Government.
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