Initial troops cross the San Juan River and are pinned down A company from the Signal Corps ascended in a
hot air balloon to
reconnoiter the hills. The balloon made a good target for the Spaniards. Hawkins' brigade had already passed by the newfound route and Kent ordered forward the brigade under Colonel
Charles A. Wikoff. Wikoff began heading down the trail at noon, and 30 minutes later he emerged from the woods and was struck by a Mauser bullet. He died as his staff officers carried him to the rear. Lt. Col. William S. Worth, next in rank, assumed command, but within five minutes fell wounded. Lt. Col. Emerson Liscom assumed command and within another five minutes received a disabling wound. Lt. Col.
Ezra P. Ewers, fourth in command of the brigade, assumed command. Kent and Sumner lined up for the attack and waited for Lawton's division to arrive from
El Caney. Lawton did not arrive as scheduled, and no orders came from either Shafter or Wheeler. Crossing the San Juan River, increasing numbers of troops waited at the base of San Juan Hill. Waiting for orders, they were plagued by constant Spanish Mauser gunfire firing down at them from San Juan Heights. The troops would call their precarious position, "Hell's Pocket" and "Bloody Ford".
The Attack on San Juan Hill As men waited at the base of the hill, General Hamilton Hawkins' 1st Infantry Brigade was preparing to assault San Juan Hill, the higher of the two hilltops forming San Juan Heights. The southernmost point was most recognizable for the Spanish blockhouse, a defensive fort that dominated the crest. The Cavalry Brigade then moved into position. Continuing to wait for orders from General Shafter, the Americans suffered casualties from rifle and artillery fire. As the volume of fire increased, officers began to agitate for action. The 16th Infantry followed some distance behind the lead formations, while the
71st (New York Volunteer) infantry regiment, having failed to initially advance with the other regiments, remained at the rear. As the units began their advance up the hill, they became separated, with the battalions of some regiments placed between those of other regiments. , 1898 The Fifth Corps' newly formed Gatling Gun Detachment participated in the U.S. Army's first use of machine gun fire for mobile fire support in offensive combat. Because U.S. black-powder artillery pieces lacked the range to reach the Spanish positions, Lt. John Parker's Gatling battery of four .30 caliber 10-barrelled guns was originally conceived as providing covering fire for the artillery trains. The Gatling Gun Detachment was ordered to move forward in support of the U.S. assault, and Lt. Parker received orders from his colonel to detach one gun to General Shafter's aide, Lt. John D. Miley, then to take the remaining three guns forward "to the best point you can find". Parker set up his three Gatlings approximately from the San Juan Hill blockhouse and its surrounding trenches, occupied by Spanish regulars; away was another ridge-line, also with Spanish entrenchments. Being exposed, the Detachment soon came under attack and quickly lost five men to wounds and others to severe heat stroke. Ordinarily, four to six men were required to operate each Gatling gun. Nevertheless, the crews continued to fire at the Spanish. Lt. Parker's three rapid-fire Gatlings provided covering fire for U.S. forces assaulting both hills. Equipped with swivel mountings that enabled the gunners to rake Spanish positions, the three guns poured a continuous and demoralizing hail of bullets into the Spanish defensive lines. Witnessing the assault on San Juan Hill, more than one observer from the U.S. side noticed some of the Spanish defenders fleeing their trenches to escape the intense fire. The Gatlings continued to fire until Lt. Parker observed Lt. Ferguson of the 13th Infantry waving a white handkerchief as a signal for the battery to cease firing to avoid causing friendly casualties. The American assault then broke into a charge about from the crest of the hill. Major
William Auman was the first commanding officer to reach the top of the hill. Lt. Ord was among the first to reach the crest of San Juan heights. As the Spanish fled, Lt. Ord directed supporting fire into the remaining Spanish until he was mortally wounded by a shot to the throat. General Hawkins was wounded shortly after. General Wood sent requests for General Kent to send up infantry to strengthen his vulnerable position. When General Wheeler reached the trenches, he ordered
breastworks constructed. The Americans' position on San Juan was exposed to artillery fire from within Santiago, and General Shafter feared the American position on Kettle Hill was vulnerable to counter-attack by Spanish forces. A Spanish counter-attack was launched late in the afternoon, but was easily beaten back with the aid of supporting Gatling fire from San Juan Hill. Though General Wheeler assured Shafter that the position could be held, Shafter nevertheless ordered a withdrawal. Before the men on Kettle Hill could withdraw, General Wheeler called aside Generals Kent and Sumner and reassured them that the line could be held. During the night, the Americans worked at strengthening the lines while awaiting reinforcements.
Col. Egbert, commander of the 6th Infantry assaulting San Juan Hill, stated that his regiment was brought to a halt near the top of the hill to await the cease-fire order, as the Gatling fire striking the crest and trench line was so intense. Roosevelt observed that the hammering sound of the guns raised the spirits of his men: "While thus firing, there suddenly smote on our ears a peculiar drumming sound. One or two of the men cried out, 'The Spanish machine guns!' but, after listening a moment, I leaped to my feet and called, 'It's the Gatlings, men! Our Gatlings!' Immediately the troopers began to cheer lustily, for the sound was most inspiring." Under continuous fire, the advance slowed as troops dropped from heat exhaustion. Officers from the rest of Wood's brigade, along with Carroll's, bunched up under fire. When the regulars of the all-black Buffalo Soldiers punched toward the top of the hill, the units became intermingled. One of the 10th's officers who took part in the attack, 1st Lieutenant
John J. "Black Jack" Pershing, would later reach the highest rank ever held in the United States Army by a living officer
General of the Armies of the United States. Pershing later recalled that: When the American formations (10th, 3rd, and 1st Volunteers) reached the summit of Kettle Hill, they briefly fought hand to hand within the Spanish defensive works, at which point the Spanish retreated. Most reports name the first American soldier to reach the crest of Kettle Hill as Sgt. George Berry of the 10th Cavalry, who took both the 10th and 3rd Cavalry battle flags to the summit. This is supported in the writings of Pershing, who fought with the 10th on Kettle Hill and who was present when Col. Roosevelt reached the top. Politics and racial discrimination led to many myths about the African-American involvement in the fighting in Cuba. Second Lieutenant
Thomas H. Rynning is credited with being the first Rough Rider to reach the top of the hill, where he rallied his men with the Rough Riders' flag. General Linares's troops on San Juan heights fired on the newly won American position on the crest of Kettle Hill. The Americans returned fire on the entrenched Spanish troops. to join the advance, which had successfully reached the heights.
Spanish counterattack Witnessing the assault on San Juan Hill, Col. Roosevelt decided to cross the steep ravine from Kettle Hill to San Juan Hill to support the ongoing fighting. Calling for his men to follow, he ran forward, only to find just five of the Rough Riders following him (most had not heard his command). Roosevelt returned, gathered a larger group of men. Under advice he led them down the less steep western slope of Kettle Hill, past a small lagoon, and was ready to start up the northern extension of San Juan Hill. By then the fighting was over at the top of the heights. General Sumner intercepted Roosevelt and angrily ordered him to return to Kettle Hill immediately to prepare for the expected counterattack. When he returned, his men were exhausted and his horse was spent from the heat. When the expected counterattack came, these men were ineffective. After the Spanish positions atop San Juan Hill had been taken, two of Lt. Parker's Gatling guns were dragged by mules up the slope to the captured position on San Juan ridge, where both were hurriedly emplaced among a line of skirmishers. As the Americans were setting up the guns, the Spanish commenced a general counterattack on the heights. Though the attack on San Juan was quickly broken up, the men on Kettle Hill faced a more serious attack from some 120 Spanish regulars. Ignoring an order from Col.
Leonard Wood to reposition one or two of his Gatling guns to the top of Kettle Hill to support the 1st Volunteer and 3rd Cavalry, Parker instead ordered the closest Gatling, manned by Sgt. Green, to fire obliquely against 600 enemy soldiers attacking Kettle Hill. , c.1899 After the counterattack was driven off, Lt. Parker moved to Kettle Hill to view the American positions, where he was soon joined by Sgt. Weigle's Gatling and crew from San Juan, detached to the service of Lt. Miley. Miley (who was primarily tasked with inspecting troop positions for General Shafter) had restrained Weigle's crew from opening fire during the entirety of the fighting. == Aftermath ==