The process of landing some 16,000 troops on the shores of Cuba was an ambitious effort that was poorly accomplished due to poor prior planning and lack of suitable landing craft.  The landings at Daiquiri that began on June 22nd stretched into days.  As the first troops under Generals Lawton and Wheeler moved westward to secure Siboney, naval transport ships moved along the coast waiting to unload additional troops.  Even as the American soldiers tasted first blood at Las Guasimas, the men of the all-Black 9th US Cavalry were finally leaving the cramped and stuffy quarters of their transport on the beaches just south of Siboney.

As these and other arriving troops from Daiquiri began moving inland, the dismounted cavalry under General Wheeler and the infantry under General Lawton moved ahead of them, following the main routes to Santiago.  General Wheeler's two brigades of dismounted cavalry made camp at El Pozo, to the northwest of Siboney and less than five miles from Santiago.  This force included Colonel Henry Carroll's three regiments (3d, 6th and 9th US Cavalries) and the newly promoted Brigadier General Leonard Wood's brigade consisting of the 1st US Cavalry, the all-Black 10th US Cavalry, and Colonel Roosevelt's Rough Riders (1st US Volunteer Cavalry).  Strung out along the Santiago road from El Pozo to Siboney and east to Daiquiri were the men of Brigadier General J. Ford Kent's 1st Infantry Division.

By the last day of June, the first soldiers to land on Cuban shores had already endured more than a week of the temperamental tropical climate, and several had become ill.  More than a century earlier Yellow Fever and other tropical ailments had thwarted the British forces in Cuba, and General Shafter was eager to press his attack before it could take a greater toll on his on men. 

On June 30th General Shafter rode his horse to El Pozo to plan his attack.  Joined by most of his command staff, he made a personal reconnaissance while his chief engineer officer Lieutenant Colonel George McClellan Derby surveyed the Spanish positions from a large balloon.  Most of the enemy soldiers were stationed in and immediately around the city of Santiago, a force of some 10,000 well entrenched Spanish soldiers and marines under General Arsenio Linares y Pombo.  To the west of the city, Cuban General Calixto Garcia Iniguez blocked any reinforcement of the Spaniards from the inland which, when coupled with the US Naval blockade of the harbor entrance, virtually isolated the Spanish ground forces as well as Admiral Cervera's squadron of ships.

General Shafter concluded that the key to taking Santiago lay first in taking the heights overlooking the city from the east.  The high ridgeline, just north of the small city of San Juan and west of the San Juan River, was known as San Juan Hill.   Rising up from the jungle below, the hill was well defended by 750 Spanish soldiers in heavily fortified positions, and dominated by large blockhouses.  Two modern howitzers provided artillery support as well.  If the Americans could take and hold this position, they would have a commanding view and a tactical advantage over the 10,000 enemy in the city below.

His reconnaissance completed, General Shafter met with General Kent of the 1st Division and Brigadier General Samuel Sumner, who had taken command of the cavalry after General Wheeler had fallen ill, to outline his battle plan.  On the following morning Kent would move his forces to storm and capture San Juan Hill, flanked on the right by Sumner's cavalry.   To prevent the enemy from sending reinforcements to San Juan Hill from their garrison at El Caney to the North, General Lawton would march his infantry to capture the city, then pull back to reinforce General Sumner's cavalry on the north end of the heights.  General Lawton predicted that it would take about two hours to accomplish his first mission, thus his soldiers would engage the enemy first while the attack at San Juan was held back until he had taken the city. 

El Caney

Spanish General Vara Del Rey had turned the town of El Caney into a virtual fort, houses along each small street serving as well defended barricades to any opposing force.   His 520 soldiers were well entrenched inside six heavy timber blockhouses and held a fortified stone church at the highest point of the town, called El Viso.  The enemy was well prepared when General Lawton's 3,500 soldiers began their assault.  One Spanish account of the battle stated:

"The houses of El Caney...vomited out a rain of bullets over the enemy (Americans), who, in order of companies, with their chests as their only protection, fiercely to run over the village.
"The Americans, to tell the truth, fought that day showing a determination and courage that was really magnificent.  With the first line decimated, another one came to its replacement, and one after another...but they met heroes, and even with the houses riddled with bullet holes by artillery and rifle fire, and its streets obstructed by the wounded and dead bodies, El Caney became a true volcanoe (sic) vomiting lava, and a place impossible to reach."

Sergeant Major Frank Pullen of the all-Black 25th Infantry Regiment later recalled the scene of battle from the American perspective.  "It (the charge on El Caney by his unit) was not the glorious run from the edge of some nearby thicket to the top of a small hill, as many may imagine.  This particular charge was a tough, hard climb, over sharp, rising ground, which, were a man in perfect physical strength, he would climb slowly.  Part of the charge was made over soft, plowed ground, a part through a lot of prickly pineapple plants and barbed-wire entanglements.  It was slow, hard work, under a blazing sun and a perfect hailstorm of bullets."

The advancing Americans found themselves facing snipers in the surrounding trees, fences to slow their progress, and that perfect hailstorm of bullets confronting them from the front.  At 10 o'clock the 17th Infantry, which had been held in reserve, was ordered forward to take a high embankment that was providing a tactical advantage to the entrenched Spanish.  Lieutenant Colonel Haskell and his regimental quartermaster Lieutenant Dickinson led forward movement, advancing in front of their men.  Four hundred yards from the Spanish line they stumbled upon occupied trenches, both falling quickly to enemy fire.  Lieutenant Dickinson, the lesser injured, rushed back to the regiment where he found Company C advancing under Lieutenant Benjamin F. Hardaway.  "The Colonel is shot!" he shouted, struggling to stem the flow of blood from his own wounded arm.

Lieutenant Haradaway, Second Lieutenant Charles Roberts, along with Corporal Ulysses Buzzard sprang into the open to go to the rescue of their commander.  Behind them followed four young Army privates, George Berg, Oscar Brookin, Thomas Graves, and Bruno Wende.  In the fierce onslaught of enemy fire that met their valiant attempt to rescue their wounded colonel, Berg and Brookins were quickly wounded but managed to drag their shattered bodies back to safety.  The remaining five men reached Colonel Haskell, half dragging and half carrying him to safety.  Colonel Haskell's wounds were far too serious to save his life, but for their valiant effort to rescue their commander in the face of a withering enemy fire, all seven men would be subsequently awarded Medals of Honor.  Throughout the day, both at El Caney and three miles south at San Juan Hill, other brave men would risk their lives for their wounded comrades.

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As the early morning assault at El Caney turned into continued battled throughout the afternoon, the main force under Generals Sumner and King could wait no longer.  Without the flanking support of General Lawton's Division, the order was given to advance towards San Juan Hill.  And there this force would find a similarly stiff resistance.

Shortly after Captain Grimes battery concluded its 8:00 A.M. initial 45-minute barrage on San Juan Hill, General  McClernand rode to the front to meet with General Kent.  Pointing towards the blockhouse that dominated the heights of San Juan hill he told the commander of the 1st Infantry Division to prepare his men to take the position.  Meanwhile, he ordered the Cavalry forward and to the right "to connect with Lawton"...unaware that Lawton's men would spend the entire day fighting for survival and victory at El Caney.  While the infantry held its position, General Sumner's two brigades moved down the jungle trails, past the infantry and towards the San Juan valley and the river crossing.  Along their route they were subjected to constant sniper fire from the surrounding jungles, and casualties mounted long before the anticipated assault could be ordered.

Behind General Wood's brigade, four men towed a large balloon from which Lieutenant Colonel Derby and Signal Corps Major Joseph Maxfield scanned the terrain.   It was a bad mistake with significant consequences.  While the observation balloon gave Derby and Maxfield a good sense of the friendly movements, the enemy positions, and the preferable routes to their objective, it also broadcast to the enemy the exact position and movement of the cavalry.  The Spanish zeroed in on the balloon from the heights as well as from the jungle below, and released a torrent of leaden death; most of which fell on the soldiers below.  As the balloon came under fire, it gradually descended; directly in the middle of the 1st and 10th Cavalry as they forded the river.  Attracting enemy fire like a magnet, the result was immediate, devastating, and tragic.

Astride his pony Texas, Colonel Roosevelt hurried his regiment across the knee-deep ford of the San Juan River and into position below San Juan Hill.  Slightly forward of the Rough Riders were the soldiers of Colonel Henry K. Carroll's 1st Brigade,  lined up for assault with the 6th US Cavalry in the center, flanked on the right by the Buffalo Soldiers of the 9th Cavalry and on the left by the 3rd Cavalry.  Coming up from behind to take a position to the left of the Rough Riders was the 1st US (Regular) Cavalry Regiment, followed by the 10th Cavalry.

 

The high ridge that was known as San Juan Hill was actually two hilltops, separated by a slight ravine.  The southernmost point was most recognizable for the blockhouse that dominated the crest.  Across the ravine to the north was another large blockhouse, and this hill would come to be known as KETTLE HILL.  By 11 o'clock most of the 15 regiments tasked with wresting control of the two hills had crossed the San Juan River and were prepared for the assault.  Below San Juan Hill the soldiers of General Kent's Division continued to return fire on the enemy as they awaited orders.  To the Division's right the dismounted cavalry was poised to attack Kettle Hill.  Despite his illness, the venerable General Fighting Joe Wheeler rode his horse to the front to watch his men, now under the leadership of General Sumner, fight their way through the blockhouses and enemy trenches to reach the top of Kettle Hill.

Over the next two hours the American struggled to survive while awaiting the arrival of General Lawton's brigade from El Caney.  During the period the enemy fire continued to rake into their ranks with devastating effect, causing Roosevelt to later write, "While we were lying in reserve we were suffering nearly as much as afterward when we charged.  I think that the bulk of the Spanish fire was practically unaimed, or at least not aimed at any particular man...but they swept the whole field of battle up to the edge of the river, and man after man in our ranks fell dead or wounded, although I had the troopers scattered out far apart, taking advantage of every scrap of cover."

Among the casualties during this dangerous few hours before the famous assault that would captivate history books for decades to follow, was the popular and famous former sheriff and mayor of Prescott, Arizona, Bucky O'Neill.  Roosevelt described it as the "most serious loss that I and the regiment could have suffered."  O'Neill was instantly killed when a Spanish bullet struck him in the mouth and passed through to exit the back of his head.  (A memorial to Bucky O'Neill is still prominently displayed in his hometown.)

 

It was almost one in the afternoon when General Shafter became finally convinced that General Lawton's division was not going to arrive from its "victory" at El Caney to attack the hill from the north and ordered, "The heights must be taken at all costs."  A few minutes later Lieutenant John H. Parker arrived with four, horse-drawn Gatling guns.  When the Spanish positions had been pointed out to him, he set his guns up and began raining heavy fire across the hillside.  The hum of the quick-firing Gatlings peppered the enemy and elicited cries of joy from the Americans digging for shelter from the Spanish guns above.  

These events that followed became more than a military action, they became one of those spontaneous occurrences that are the lore of military legend.  The men of Shafter's Fifth Corps had been ordered to the foot of San Juan Hill in a plan the General frankly admitted amounted to "going straight at them (the enemy)."  Of a truth, there was nowhere else to go.  The fierce shelling of the enemy artillery, coupled with the forward press of the rear regiments of the force, literally trapped the forward regiments, preventing any retreat.  The devastating fire that rained on the men below San Juan and Kettle Hills continued unabated, and the only way to silence those guns was to charge and take the hill.  The steady drum roll of Lieutenant Parker's Gatling's gave the hard pressed cavalry and infantry soldiers an infusion of new hope.  It was a moment ripe for something extraordinary to occur, a moment for individual valor to claim the day...it was a moment for history.  

"It was a moment pregnant with heroism," historian Henry Watterson wrote shortly after the battle.  "It was delivered of thousands of heroes."  

It was a moment that Colonel Theodore Roosevelt would call:

"The  Crowded  Hour".

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