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Reveille sounded before the sun could light up the tropic sky. Blue-clad soldiers with only a few hours’ sleep shook off their stiffness, and orders circulated among them to strike their pup tents. As the gray light of dawn slowly crept across the eastern Cuban sky, tropical birds squawked to announce the beginning of the first day of July 1898.

Regiments of American troops were camped along the Santiago Road for several miles back toward Siboney. Brigadier General Samuel S. Sumner’s Cavalry Division of two brigades rested below El Pozo Hill. Because of the limited sea transport available when the Americans landed at Daiquirí on June 22–barely enough to accommodate the troops, let alone horses–the dismounted cavalry would have to fight as infantry. Only the artillery, supply trains, officers and their orderlies retained their mounts.

Colonel Henry K. Carroll commanded the brigade of the 3rd, 6th and 9th (Colored) U.S. Cavalry regiments, while Colonel Leonard Wood commanded the brigade of the 1st and 10th (Colored) U.S. cavalries, along with the 1st U.S. Volunteer Cavalry, known as the ‘Rough Riders.’ A Harvard graduate and surgeon, Wood had established his military reputation in the 1886 campaign against the Apache warrior Geronimo, during which he received the Medal of Honor. Wood had assumed command of the brigade after Sumner had relieved the division’s ailing original commander, Maj. Gen. Joseph Wheeler.

Along the road behind El Pozo waited Brig. Gen. Jacob Ford Kent’s 1st Division. Brigadier General Hamilton S. Hawkins commanded the 1st Brigade, which included the 6th and 16th U.S. Infantry and 71st New York Volunteer Infantry regiments. Close behind him were Brig. Gen. Charles A. Wikoff and his 2nd Brigade, comprised of the 9th, 13th and 24th (Colored) U.S. Infantry regiments. Then came Brig. Gen. E.P. Pearson’s 3rd Brigade, made up of the 2nd, 10th and 21st U.S. Infantry regiments.

The previous morning, Maj. Gen. William R. Shafter, commander of the V Corps, had ridden up to El Pozo to survey the heights around Santiago de Cuba and El Caney. His staff accompanied him–Lt. Col. Edward J. McClernand, Lt. Col. George McClellan Derby, Lt. Col. John D. Miley and Lieutenant R.H. Noble. Derby, the chief engineer officer, went up in a hydrogen balloon to observe the proposed battlefield. At noon, Brig. Gen. Henry W. Lawton, commander of the 2nd Division, and Brig. Gen. Adna R. Chaffee, commanding that division’s 3rd Brigade, joined the staff on their ride.

When Shafter completed his reconnaissance, he summoned Kent and Sumner to outline a plan of action.The ground assault on the city of Santiago was part of a joint Army-Navy operation to capture or destroy the Spanish cruiser squadron trapped in the bay. The dominating heights around the city, defended by 750 men and two modern howitzers, was the primary Army objective. Spanish General Arsenio Linares y Pombo had placed most of Santiago’s garrison of 10,429 soldiers, sailors, marines and more artillery at other points around the city, or in reserve. To the north, 3,000 Cuban insurgents under General Calixto García Iñiguez blocked the arrival of any Spanish reinforcements along the Cobre Road. Northeast of the city, 520 Spanish troops, commanded by Brig. Gen. Joaquín Vara de Rey y Rubio, occupied El Caney. Because reinforcements could move down the road from El Caney and threaten Shafter’s right flank, he proposed that Lawton capture the town. Lawton claimed that he could take it in two hours. Shafter detached Captain Allyn Capron’s howitzer battery to support Lawton.

Sumner and Kent would advance along the main road to Santiago, then cross the Aguadores River, with Sumner deploying his brigades to the right and Kent to the left. After he captured El Caney, Lawton would line up to the right of Sumner. Captain George Grimes’ howitzer battery would support the main effort.

In the light of early dawn on July 1, the men ate a meal. Rumors flew about the day’s events. The bugles then sounded attention, and the soldiers lined up in double columns on the dusty road. At the head of each regiment the commander stood next to the regimental and national colors, which were cased in oilcloth covers. Bugles sounded again, and the troops moved forward. As regiment after regiment marched down the road to Santiago, McClernand and Miley of Shafter’s staff rode through the troops with their orderlies to coordinate the battle from the front. Shafter was in his tent, too ill to actively participate, and McClernand set up on El Pozo Hill, where he could communicate with Shafter by wire telephone and mounted orderlies.

With blanket rolls slung over their shoulders and haversacks by their sides, the men trudged forward along the narrow road. At about 6 a.m., Grimes’ battery raced past the soldiers and up El Pozo Hill, where the artillerymen positioned the howitzers with their barrels aimed toward Santiago. Miley then rode to Shafter’s headquarters to report on the troops’ progress.

Around 7 o’clock, the sound of distant thunder to the north signaled that Capron’s battery had opened the battle for El Caney. By then, Wikoff’s brigade had joined the march. The remaining cavalry regiments pressed forward to join Sumner’s men at El Pozo. Infantry regiments crowded up against the cavalry, with as many as three regiments abreast. Journalists rode up and down the columns. Most of the correspondents, foreign military observers and senior officers enjoyed the view from El Pozo.

After he heard firing on El Caney for an hour, McClernand turned and gave Grimes permission to open his own cannonade, and clouds of white smoke billowed from the howitzers. Colonel Wood looked down on his brigade and commented to Lt. Col. Theodore Roosevelt that he wished the troopers were out of the line of fire. Moments later, a whistling sound split the air, followed by an explosion and then another as two quick-firing Spanish Krupp guns answered Grimes’ fire. A third round struck the little house on El Pozo, spraying shrapnel that killed two and wounded several other spectators. Before the next volley, men above and below the hill scrambled for cover, leaving Grimes’ battery alone to do its work. It continued to pour rounds into the enemy for nearly three quarters of an hour, but the smoke obscured Grimes’ view of the Spanish artillery.

Miley soon returned to El Pozo. The sound of the guns had stirred ‘Fighting Joe’ Wheeler to join the troops there. The former Confederate cavalry leader became the senior officer at the front and worked closely with McClernand. McClernand instructed Wood and Sumner to form their brigades and advance. Sumner asked, ‘What do I do then?’ ‘You are to await orders,’ replied McClernand.

McClernand then pointed to the blockhouse on San Juan Hill and told Kent that it was his objective. Kent was directed to follow closely behind the cavalry and deploy to the left, with his right anchored on the Santiago Road. Kent then passed on the same instructions to Hawkins. Neither had reconnoitered the area.

Miley rode to the front with his mounted orderlies to provide communications with McClernand. Passing Kent, he told him to give right of way so the cavalry could get into position first. At 9 o’clock, the cavalry column advanced down the jungle trail. Carroll’s brigade led, followed by Wood’s brigade and then Hawkins’. When the lead cavalry brigade reached the San Juan River, the men waded through the knee-deep water regiment by regiment and then peeled off to the right.

Kent and Hawkins, joined by Miley, rode to the river crossing to reconnoiter. Hawkins believed his brigade could ascend the hill, storm the blockhouse and then turn the Spanish flank. Kent had his doubts. Miley agreed with Hawkins, however, and with the authority delegated to him by Shafter, he directed Hawkins to take the hill. Riding back, Hawkins squeezed past the cavalrymen who were bottled up at the crossing, completing their slow deployment into a line. About that time, a dynamite gun and a battery of Hotchkiss guns arrived. Roosevelt claimed the dynamite gun, and Hawkins took command of the others.

With the men advancing down the road well within range of enemy guns, Shafter ordered Grimes’ battery to again open fire. At 10 o’clock, his howitzers belched fire and smoke, but to everyone’s surprise, the Spaniards did not answer. By that time, Captain Robert Lee Howze of Carroll’s staff rode up to report that his brigade had crossed the Aguadores. Meanwhile, Sumner had ordered Wood’s brigade forward. The heat rose as the tropic sun climbed high in the sky. Concealed in the trees along the road, snipers dressed in quilted canvas tunics filled with sand and covered with palm leaves formed the forward skirmish line of the Spanish defense force.

Behind Wood’s brigade, four soldiers towed a balloon. On his own initiative, Derby ascended just above the trees in the partially filled balloon along with Major Joseph Edwin Maxfield of the Signal Corps, who commanded the balloon company. If the Spaniards had any doubt as to the Americans’ location, the sight of the rising balloon removed it. Mauser rounds and artillery shells began to cut through the air, snapping leaves and branches before finding their targets–the American soldiers below. The riddled balloon returned to earth, but not before Derby obtained one bit of useful information.

As Kent’s infantrymen pushed past the deflating balloon, Derby informed their commander of another trail several hundred yards up from the Aguadores to the left of the main trail. Since the cavalrymen still blocked the main road, Kent’s infantrymen could bypass them and more directly reach their assault positions on the left. The 6th and 16th Infantry regiments of Hawkins’ brigade had already passed the turnoff, so Kent turned the next regiment in line.

The 71st New York Volunteer infantrymen did not possess the same seasoned discipline and training as the Regulars. Demoralized by the incoming fire, they advanced down the new trail only a short distance before they froze. Kent and his aides rode up and reprimanded the men, but they would not budge. The officers then ordered the volunteers to make way for others, and Kent sent back for Wikoff to push his brigade through.

First Lieutenant Wendall L. Simpson ran back, waving his hat for Wikoff to hurry his men forward. Wikoff was leading his brigade down the trail and into the opening when at 12:30 p.m. he fell wounded. As some of his men carried him back in an abandoned chair they had found, he waved to the rest and cried, ‘Get on up, boys, they need you–hurry!’ Then he died.

Simpson turned to the first commander in line, Lt. Col. William S. Worth, and instructed the new brigade commander to hurry his 13th Infantry across the ford. Five minutes after Wikoff had fallen, a Spanish round hit Worth in the chest. His sword dropped from his hand, but he remained mounted, retrieved his sword with his left hand and waved it to his men. In spite of his determination, loss of blood forced him to the rear. Five minutes after Lt. Col. Emerson H. Liscum of the 24th (Colored) assumed command of the brigade, he, too, fell wounded. At last, Simpson reported to Lt. Col. Ezra P. Ewers, commander of the 9th Infantry, who brought the remainder of the brigade forward while another staff officer rode back to bring up Pearson’s brigade.

Meanwhile, shouts and insults rang out as the Regulars squeezed by the cowering New Yorkers. Little by little, the jeers goaded the volunteers to join in the advance. After Hawkins drew his 6th and 16th into line to the left of the Siboney Road, he looked for but could not find his reserve. He did not know that Kent had diverted it. With the exception of two companies, the 71st had ceased to exist as a unit. The American plan was beginning to unravel.

In the valley of the San Juan River, north of the road to Santiago, Sumner’s cavalry division had lined up for the impending assault. Carroll’s brigade formed the first line. His 9th (Colored) held the right, the 6th was in the center and the 3rd was on the left. Behind the 9th waited Roosevelt’s Rough Riders. To his left and a little forward rested the 1st, with the 10th (Colored) behind it in reserve. To the immediate front of the cavalry division rose the hill, topped by a few buildings, that would be their objective. Capturing ‘Kettle Hill,’ named by the Americans after a large iron kettle they found on it, would provide a foothold to the San Juan Hill complex.

Hawkins’ two regiments anchored on the road awaited Ewers’ brigade. The 13th arrived in the lead, then the 24th (Colored) followed by the 9th Infantry. Pearson followed with his brigade. Kent directed Pearson to deploy his 10th and 2nd Infantry regiments to the extreme left and send the 21st down the main road to join Hawkins as his reserve. Eight rows of barbed-wire fences stretched between Kent’s infantry and the Spanish trenches.

Both the heat and Mauser fire became more intense. The men sought cover in the folds of the ground or behind brush, and officers walked among their men to bolster flagging morale. The Americans returned the Mauser fire, which did little good against the entrenched Spaniards. Casualties mounted as the senior officers waited for Lawton’s division to arrive, but that tenacious officer was still trying to take the blockhouses at El Caney. The Spanish defenders there fought with equal resolve until their ammunition ran out and their heroic commander, Vara de Rey, was killed.

No further orders came from General Shafter, who could not even see the battle. In sections along the river that they would later call ‘Hell’s Pocket’ and the ‘Bloody Ford,’ the men waited while Mauser bullets claimed more lives. The wounded who could walk made their way back to the aid station at the crossing of the Aguadores. Only storming the heights would silence the Spanish guns and finally end the killing.

The senior American officers had seen service in the Civil War. That conflict had trained them to await orders and follow them. Their company and junior field grade officers, in contrast, had begun their careers fighting Indians. The isolation of frontier garrisons and small-unit operations had accustomed them to acting on their own initiative.

Lieutenant John H. Parker raced down the main road with his four horse-drawn Gatling guns. ‘Where in the hell are the Spaniards?’ he exclaimed. ‘I’ve been fighting all day and haven’t seen a damned one!’ A captain graciously pointed to the top of the ridge. Parker thanked him and pulled his guns off to the side of the road. At 1:15, he placed them into action.

Lieutenant Jules Garesche Ord of Hawkins’ staff had remarked to a friend that he would come out of this battle either as a colonel or a corpse. Seeing the futility of remaining exposed to galling fire, he told Hawkins, ‘General, if you will order a charge, I will lead it.’

Ord’s commander remembered the costly charges against an entrenched enemy during the Civil War. He said nothing. At about that same time, they heard the pounding of Parker’s Gatlings.

Ord again spoke up: ‘If you do not wish to order a charge, General, I should like to volunteer. May I volunteer? We can’t stay here, can we?’

‘I would not ask any man to volunteer,’ replied the general.

‘If you do not forbid it, I will start it,’ returned Ord.

Hawkins pondered the situation for a moment. He observed the impact of the Gatlings kicking up clouds of yellow dust on the Spanish entrenchments. The other two brigades were not yet on line.

Undaunted by the silence, Ord again spoke up, ‘I only ask you not to refuse permission.’

Hawkins looked at this enthusiastic young officer. ‘I will not ask for volunteers, I will not give permission and I will not refuse it,’ he said. ‘God bless you and good luck!’

A smile flashed across the lieutenant’s face. With pistol in one hand, sword in the other, he ran forward at a crouch, shouting: ‘Come on–come on, you fellows! Come on–we can’t stop here.’

A spontaneous cry went up along the line. The waiting under fire was over. The men moved forward with Ord in the lead. Hawkins positioned himself between his two regiments and encouraged his men along the way.

As soon as the 13th Infantry came into the clearing, its men began to fall under the heavy enemy fire. Major William Auman, who had assumed command of the regiment after two senior officers were wounded, ordered his men to a gentle rise 100 yards to his front that offered some shelter and waited for the 24th Infantry to line up on his left. A sergeant in the 24th then sprang to his feet, shouting: ‘Come on, boys! Let’s knock the hell out of those sons of bitches!’ The 24th advanced, followed by the 9th Infantry and then the 13th.

A ragged blue line of four infantry regiments on line and one in reserve moved across the open valley in a series of short rushes with flags waving, the troops firing and advancing the 600 yards in no real order. They cut their way through the wire fences. The Spaniards increased their fire, and with each advance more men fell. The Americans were 150 yards from the foot of the hill when, without orders, the 6th Infantry’s bugler sounded the long notes of ‘Charge!’ Another yell rang out, and the men ran for the hill. All the while Parker advanced his Gatlings with the infantry and, with at least three working guns, sprayed the enemy trenches.

Across the road, Roosevelt had already lost several of his company officers while waiting for messengers to find either his brigade or division commander. Impatient with the mounting casualties, he decided that in the absence of orders he would lead the charge himself. As a politician, Assistant Secretary of the Navy Roosevelt had come to Cuba to earn glory, and he lacked the disciplined obedience of the Regular Army officers.

At McClernand’s request, Wheeler rode forward and passed on instructions to Kent to advance. Wheeler then rejoined his cavalry division, and Sumner rode back among the men of the 10th Cavalry to give them the order to advance. Lieutenant Colonel Joseph H. Dorst rode up and told Roosevelt ‘to move forward and support the Regulars in the hills in the front.’ Roosevelt called his regiment out from cover and formed it into a column with each troop on line. Exhausted from the tropical heat, he feared that he could not keep up with his men, so he remained mounted, posting himself properly behind his regiment. The cavalry division advanced. No one, however, gave the order to attack.

The lead elements of the cavalry slowed their pace as men fell from the effects of the heat and bullets. Rear troops crowded into those in front until entire regiments merged into one line. The 1st and 9th cavalries overtook and intermingled with the Rough Riders. The 3rd, 6th and 10th cavalries followed and tied in with the infantry on the left.

The cavalry had the shortest distance to cover. The first line reached the road halfway up the hill, then dropped behind the cover of a depression. Roosevelt’s regiment caught up with the 9th, and he told a captain in command that they ‘could not take these hills by firing at them’ and that ‘we must rush them.’ The captain replied that he could not do so without orders and could not find his commander. ‘Then I am the ranking officer here,’ Roosevelt replied, ‘and I give the order to charge.’ The Regular Army officer still hesitated to follow the order of a volunteer officer, at which point Roosevelt said, ‘Then let my men through, sir.’ With that, the Rough Riders passed over the prone Regulars.

Along the line, other Regular officers took the initiative. Captains John F. McBlain and Charles W. Taylor on the right flank of the 9th Cavalry ordered their own charge. As one body, the entire division again picked up momentum. The men knocked down the barbed-wire fence paralleling the road, fired and then ran, yelling, the rest of the way to the top.

Forty yards from the top, Roosevelt, riding far ahead of his men, reached the last line of wire. He dismounted and turned loose his horse, his orderly having kept up with him on foot. As troopers of the 1st and 9th cavalries and the Rough Riders swarmed over Kettle Hill, the Spaniards withdrew to the next line of trenches. The Rough Riders’ three New Mexico troops, G, E and F, planted their guidons on the hill, while Captains McBlain and Taylor of the 9th planted their guidons on the right. Taylor received a wound shortly afterward and was evacuated.

Color sergeant J.E. Andrews of the 3rd Cavalry took a round in the abdomen. He called for his lieutenant to take the colors, but then he tumbled back down the hill to the road, still clutching the flag. Sergeant George Berry of the 10th Cavalry snatched it up and carried both the 3rd’s and his own regiment’s flags up the slope, shouting, ‘Dress on the colors, boys, dress on the colors!’ Colonel Charles D. Veile placed the 1st Cavalry standard on the hill.

The Spaniards in the next trench line concentrated their small-arms fire on the cavalry. Artillery air bursts added to the American casualties. Colonel John M. Hamilton, commander of the 9th Cavalry, was killed, and Carroll was wounded. The 10th lost the most officers. By that time, Sumner rode up. Upon seeing the infantrymen climbing the other hill, the cavalrymen fired volleys of bullets on the trenches and the blockhouse in support.

Hawkins’ and Ewers’ brigades ran to the hill en masse. When they reached the foot of the hill, the troops discovered that the Spaniards had dug their trenches on the topographical crest instead of the military crest (about 10 meters below the topographical crest), and an irregularity in the 120-foot steep slope prevented them from seeing the Americans below. Grabbing tufts of grass, men scrambled up the 30-degree slope, intermingling and losing all unit integrity. They halted momentarily near the crest to catch their breath. Looking back, they saw men dead and wounded on the field but, miraculously, none on the hill.

Someone waved a white handkerchief at Parker, and at 1:23, the Gatlings fell silent and the infantry charged. As the Americans came within 30 feet of the trenches, the Spanish fled. Ord, still in the lead, leaped over the trench but was killed by a Spanish round. His soldiers were enraged by the death of their beloved hero. Auman was the first commanding officer to reach the top. The infantry finally reached the crest, only minutes after the cavalry.

Captain Arthur C. Ducat and Lieutenant Henry G. Lyon, with 65 men from their own 24th Infantry and the 6th, 9th, 13th, 16th infantries, raced for the prize–the yellow stucco home converted into a blockhouse, which 35 Spaniards defended from inside its pockmarked walls. Ducat, Lyon and a number of men fell wounded before they reached the blockhouse. Unable to break through the heavy wooden doors and boarded-up windows, 19 men climbed onto the red tile roof. Four dropped through a hole made by artillery but were then killed. The remaining 15 jumped in at once. After a few minutes of hand-to-hand fighting, the Americans had cleared the building. Private Arthur Agnew of the 13th Infantry hauled down the Spanish colors atop the blockhouse. By 1:50, the Americans had secured San Juan Hill. The 13th and the 24th suffered the heaviest casualties in the infantry assault.

Men in blue swarmed over the hill and drove their company guidons and regimental colors into the ground. The hill resounded with ‘cease fire,’ echoed by bugle calls. The men of the 71st New York sought out their officers. Some men asked Major Auman if they should continue on to the second line of entrenchments. He ordered them to hold what they had and fire on the fleeing enemy.

The Spaniards retired across a valley to their next line of trenches on the left. Americans scrambled for cover as Mauser fire resumed and again had deadly effect on any exposed troops. A colonel and a number of troops were hit while standing by the door of the blockhouse.

The 10th and 2nd infantries of Pearson’s brigade had arrived at the ford a few minutes after the advance began. They then proceeded in column toward the green knoll to the left of San Juan Hill and seized the trenches. At 2 p.m., the battery of Hotchkiss light artillery arrived on the firing line, followed by the pack train. Mules hauled food and ammunition right up to the trenches.

The cavalrymen then turned their attention to the line of trenches to their right front, to which the Spaniards had fled from San Juan Hill. Roosevelt charged. After advancing 100 yards with only five men, he turned around, ran back and scolded the rest for not following. They innocently replied that they had not heard his order. Roosevelt turned to Sumner for permission to lead the other regiments in the attack. The general assured him that the men would follow.

Cavalrymen leaped over the wire fence and raced across the valley to the next line, with Captain Eugene D. Dimmick leading the men of the 9th Cavalry. The Spaniards retreated long before the cavalry reached the trenches. Cavalrymen had swept over the palm-covered ridge and started for Santiago before Roosevelt stopped them. With a small mixed force, he commanded the extreme right of the American front.

The black soldiers had fought superbly throughout the battle, but since their officers were not with them on the hill, they began to straggle back. Roosevelt drew his revolver and headed them off. He commended them for their courage but threatened to shoot the first man who went to the rear for any reason. The black troops asked Roosevelt’s men if he would make good on that threat. The Rough Riders replied in chorus to the affirmative. The black troopers readily accepted Roosevelt as their acting commander.

Sumner kept a sizable reserve on Kettle Hill under the command of Major Henry Jackson of the 3rd Cavalry. Realizing that Roosevelt was in a precariously weak position, Sumner sent a request for an infantry regiment. Kent reached the hill that Hawkins reported his brigade had captured (neglecting to mention that the regiments of Ewers’ brigade had done so as well). Kent forwarded this report to V Corps headquarters at 3 o’clock. Ten minutes later, Kent received requests from both Sumner and Wood for assistance on the right. He sent over the 13th, and Roosevelt positioned the infantry reinforcements between his command and a small contingent of the 9th Cavalry.

Spanish cavalrymen, marines and infantrymen launched a fainthearted counterattack against Roosevelt’s position. The Americans cheered as they fired, and a few seconds later the Spaniards stopped and retreated to cover. Shortly afterward, Parker wheeled his Gatlings in on the extreme right of the Rough Riders, positioning them where he could best fire across the enemy trenches. As darkness fell and the firing ceased, the Americans commanded the heights overlooking Santiago.

Shortly after Wheeler reached the trench line, he ordered breastworks to be built and sent back for the entrenching tools that had been discarded along the road. Wheeler sent word along the line that reinforcements would soon arrive. Brigadier General John C. Bates’ Independent Brigade, however, did not arrive until midnight, when he reinforced Kent’s left. Lawton, who had finally taken El Caney at 4 p.m., did not arrive until noon the next day.

At 8:20 p.m., Wheeler reassured Shafter that his thin line could hold. Nevertheless, Shafter later ordered a withdrawal. Summoning Bates and Kent, Wheeler told them that he was the best judge of the situation. From his Civil War experience, he knew that if a force was strong enough to take a position from an entrenched enemy, regardless of the losses, it could hold out against a counterattack by that same enemy. He ordered the men to hold, and the troops realigned themselves with their proper regiments.

Although the Spaniards would bitterly contest the Americans for two more weeks, on July 17 the commander of the Spanish IV Army Corps, Maj. Gen. José Toral y Vazquez, signed articles of ‘capitulation’ (avoiding the use of the more pejorative word’surrender’) that handed Santiago over to the Americans. They had won their splendid little war.

This article was written by Richard E. Killblane and originally published in the June 1998 issue of Military History magazine.

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