The American fleet formed up outside Tampa Bay into a three-column convoy of 32 transports and five barges, escorted by a screen of torpedo boats, cruisers and the battleship Indiana. Progress was slow, and the fleet sailed south at a leisurely seven knots. It passed Key West, the main naval base at the end of the Florida Keys, then sailed south-east towards the northern shore of Cuba. It arrived within sight of the Cuban shore with lights blazing and bands playing. Foreign observers feared an onslaught by Spanish destroyers, who would find the convoy an easy target, but the attack never came. The fleet rounded the eastern tip of Cuba, then headed west, along Cuba’s southern shore. It passed Guantanamo on 19 June, unaware that the US Marines had already fought a tough action to establish a beachhead. The ships ploughed on towards Santiago.
US troops aboard a transport, within sight of the coast of Cuba. The fleet sailed with bands playing and lights blazing, almost as if inviting attack. (National Archives)
After consultation with naval and guerrilla commanders, Gen. Shafter decided to land his forces at Daiquiri. The outnumbered Spanish had already withdrawn to Las Guasimas. On the following day US troops marched to Siboney, which became the main American base. A probe to the north by dismounted cavalry commanded by Gen. Wheeler led to the skirmish at Las Guasimas. After a bitter fight in thick jungle, Gen. Rubin pulled his Spanish troops back to Santiago. The Americans slowly followed, establishing a forward camp at Sevilla. After a week of waiting for supplies and orders, they were finally ready to launch an attack on the Spanish at San Juan and El Caney. During this entire week, Gen. Linares refused to move out to meet the invaders, and the Spanish remained ensconced around the city. He hoped that formidable defences, reinforcements and the start of the yellow fever season would swing the balance in favour of the Spaniards.
As the fleet approached Santiago on 20 June, Shafter raced ahead in a cruiser for a rendezvous with Admiral Sampson and the Cuban insurgent leader, Gen. Gomez, in the hills above the coastline to the west of Santiago. They decided that a frontal assault on Santiago’s coastal defences would be extremely risky, and that the army would disembark at Daiquiri, 16 miles east of the city. From there a forward base could be established at Siboney, halfway between Daiquiri and Santiago. Sampson wanted the army to clear the way for a naval attack, while Shafter saw the campaign as an army operation, with the fleet supporting his efforts. The agreement to land the troops at Daiquiri marked the highest level of co-operation that the two branches of service would achieve during the coming weeks.
The Rough Riders pictured disembarking from the transport ship Yucatan off the Cuban coastal village of Daiquiri. This was the first amphibious landing undertaken by the army since 1865, and it was a haphazard and disorganised operation. (National Archives)
On the morning of Tuesday 22 June the fleet approached Daiquiri. Five warships bombarded the shoreline around what Roosevelt described as a ‘squalid little village’. The troops then began to disembark, and the operation quickly degenerated into a chaotic muddle. Some ships anchored miles out to sea as their civilian captains refused to risk their vessels. Others further inshore ran in front of the covering warships. There were insufficient launches to ferry the troops and equipment, and the high surf hindered the loading of the boats. Fortunately, Spanish resistance was minimal. The company-strength garrison retired when the bombardment started, so the Americans had the beachhead to themselves, apart from a handful of Cuban irregulars, who came down to the beach to watch. The Vigilancia, carrying the Rough Riders, approached within a hundred yards of the shore, and the volunteers were amongst the first troops to land. A long jetty served as a convenient landing place, but even here the operation was chaotic. Two men drowned when they fell from their boat, and the scene was made even more bizarre by the horses, which had been cast loose to swim ashore themselves.
The village of Daiquiri, pictured from a transport at anchor in the bay. Surf and hidden shoals in the bay made landings difficult, and many merchant captains refused to take their ships close to the shore. (National Archives)
Col. Wood felt embarrassed that the landing was being watched by a score of foreign observers. One journalist, Edward Marshal, led a group of soldiers to an abandoned Spanish blockhouse which commanded the village. He raised an American flag on the blockhouse flagpole, and a cacophony of ship sirens, music and cheering erupted. Daiquiri was in American hands without an enemy shot being fired.
As the troops struggled ashore during that day, they encamped wherever they could around the village and for four miles down the road towards Siboney. The landing of men and supplies continued for the next two days. An advance guard led by Gen. Lawton occupied Siboney in the morning of 23 June, seven miles down the coast towards Santiago. The fleet of transports then moved itself down the coast, and Siboney became the primary American beachhead. For most of that day and night hundreds of naked American soldiers helped to unload supplies in the surf, watched by hundreds of Cuban irregulars dressed in rags. A journalist likened the scene to ‘bathers in the surf at Coney Island on a hot Sunday’. By nightfall on the 23 June, only one brigade of Gen. Wheeler’s Cavalry Division was ready to conduct offensive operations. With reports of a Spanish defensive position four miles to the north, on the main road from Siboney to Santiago, Wheeler was ready to exploit his advantage. Cuban insurgents had skirmished with the defenders that day, and the Spanish were reportedly digging in.
SPANISH SKIRMISHERS AT LAS GUASIMAS
Gen. Wheeler ordered two columns of dismounted cavalrymen to probe up the road and nearby trail from Siboney to Sevilla: the troops set off at dawn on 24 June. Cuban insurgents had already reported that Spanish troops had been seen at Las Guasimas, where the trail and road joined. Sure enough, the Rough Riders, moving up the trail in a column, were the first to run into the Spanish advanced line. A brutal skirmish developed that soon involved the larger American column moving up the main road. The Spanish defenders took full advantage of the terrain. By hiding in trees or behind impenetrable barriers of vines and undergrowth, they were concealed from the Americans. As the Rough Riders advanced, they came across a series of small clearings flanking the trail. Each of these became a miniature battlefield, where the Spanish sharpshooters occupied the treeline at the far edge and fired at the Americans as they emerged from the jungle. They then fell back to the next clearing. It was this stage of the fighting that cost the Rough Riders the majority of their casualties. The Spanish eventually fell back through Sevilla, leaving the field to the Americans.
Before dawn on Thursday 24 June, Gen. Wheeler launched the troops of the 2nd Cavalry Brigade (dismounted) down the road towards the reported enemy positions. The rain of the night had stopped, and a wet and muddy body of troopers prepared themselves for battle. The plan was to probe the Spanish positions, with Wood leading the Rough Riders along a small trail to the west of the main road, and the remainder of the force advancing directly up the road towards the enemy. In the event of an engagement, Wood’s column would be in a position to roll up any enemy opposition to the main column by attacking the Spanish in their flank.
The Rough Riders left their encampment outside Siboney at 5:40am and climbed the ridge to the north of the town. Brig.Gen. Young’s column consisted of a squadron of the 1st US Cavalry (200 men), and a squadron from the 10th US (‘Negro’) Cavalry (220 men). Fire support was supplied by a pair of Hotchkiss mountain guns. They had already set off north along the main road from Siboney to Sevilla by the time the Rough Riders left camp. Once on the plateau above the ridge Wood located the small trail that followed the ridge on the western edge of the small valley, which ran northwards. The two American columns were therefore advancing on opposite sides of the valley, separated by just over a mile of jungle, stream and brush. Communication between the two columns was impossible due to the impenetrable terrain. The two columns would only be able to assist each other once the trails merged, at Las Guasimas. The area got its name from the Guasimas trees that grew there.
US troops landing on the coaling jetty at Daiquiri, after being ferried by naval launches. A number of soldiers drowned under the weight of their equipment as they fell from boats while disembarking. (National Archives)
Wood was subsequently criticised for failing to provide an advance guard, but several witnesses report he sent out a five-man ‘point’ of Rough Riders from the Western Territories who were trained in tracking. They were led by a Sgt. Byrne and accompanied by Sgt. Fish, a charismatic and youthful New York socialite. Cuban ‘guides’ preceded them, and the advance guard was then followed by Capt. Capron’s troop of 60 men. The jungle precluded the use of flank guards, so the main body followed this advance guard down the trail. Col. Wood rode at the head of the main body, accompanied by Lt.Col. Roosevelt.
After an hour-and-a-half of marching (which included brief rest stops), Wood halted the column and rode forward to consult with Capron, who had signalled to his commander. At this point the trail narrowed considerably and led downhill. A barbed wire fence ran down the left (west) side of the trail, with several narrow fields of high grass beyond it. These extended back about 50 yards from the trail, and were separated by tree lines running at right angles to the trail. On the right side of the track the jungle ran beside the road, and was barely open enough to allow men to move through it. Capron reported that the enemy positions lay ahead, and he had already deployed his men in a line on either side of the road. Wood explored up the trail for a few yards, then returned with orders to deploy the column. Two troops were ordered to the left of Capron’s line, and another (G Troop) to his right. Two more troops were ordered to deploy even further to the right, to attempt to link up with Gen. Young’s column on the main road. The remaining four troops stayed in reserve on the trail, and a first aid station was established where the column first halted. Capron’s troop then began a cautious advance down the trail to their front. It was now 8:15am.
Firing broke out first to the right of the trail where G Troop was deploying, led by Capt. Llewellyn. A correspondent following the men as they deployed reported that he ‘found them breaking their way through the bushes in the direction from which the volleys came. It was like forcing the walls of a maze. If each trooper had not kept in touch with the man on either hand, he would have been lost in the thicket. At one moment the underbrush seemed swarming with troopers, and the next, except that you heard the twigs breaking and the heavy breathing of the men, or a crash as a vine pulled someone down, there was not a sign of a human anywhere’.
After a few minutes, the jungle to their front opened up into a clearing, and the Spanish fire appeared to be coming from beyond the far side, about 60 yards away. All along the American line, men returned the fire. Both sides were separated by a tangle of vines and branches, so neither force could see the enemy. Within seconds a heavy firefight ensued that spread outward from G Troop to include Capron’s men and the troops to his left. To the right of the American line, two troops were still deploying. The sound of rifle fire far to the right meant that Young’s column was also engaging the Spaniards. Lt.Col. Roosevelt appeared, and ordered the troops to move to their left, cross the trail and follow Capron. This would hook the troops around the wall of vines. Because of the Spanish fire this redeployment took some time, the men having to crawl through the long grass of the clearing: eight men were left lying dead or wounded at the edge of the clearing. Roosevelt was now in command of the left flank, and was advancing to the left of the track.
American troops preparing to move out from the fields around Daiquiri, heading for Siboney. The view is towards the northwest, and the village is off to the left of the camera. The hills behind Demajayabo are seen in the distance. (Library of Congress)
By this time the columns of Wood and Young were linked by a skirmish line under the command of Capt. ‘Bucky’ O’Neill. Col. Wood now had a force of four troops bunched around the trail, and a further two troops linking them with Young’s column on the road, about 900 yards to his right. His intention was to pin the Spaniards to their front, then outflank them with the remainder of the regiment. In reality, neither he nor any other American on the battlefield had any real idea where the Spanish positions were, or how far their line extended.
On the main track, Gen. Young’s column came under fire from Spanish positions to their front and on both flanks. Fire from a number of small stone redoubts (which reportedly included machine guns) on top of a low hill prevented easy communication between the Rough Riders under Capt. O’Neill and the regulars, pinned down on the main road. Young ordered up his two mountain guns, and after a 30-minute bombardment the Spanish fire slackened.
Gen. Wheeler arrived, keen to savour his first military action since the fall of the Confederacy. He rightly assessed that his advance guard had encountered a substantial Spanish position, and ordered the rest of his division to come to their assistance from Daiquiri. The squadron of the 1st US Cavalry then pushed through the jungle to the right of the road, clearing Spanish sharpshooters from the vicinity of the two guns. The Buffalo Soldiers of the 10th Cavalry fired on the hill; then, when the 1st US Cavalry troopers joined in with supporting fire, two troops advanced in rushes, driving the Spaniards from their positions. The tide of the battle had swung in favour of Wheeler and Young. As the Americans swarmed round both sides of the ridge, the Spanish were seen to fall back to a new position, 300 yards to the rear. A fresh firefight developed, but by 10:00am the Spanish withdrew out of sight.
Gen. Wheeler, a more aggressive commander than his superior, took it on himself to probe up the road between Siboney and Sevilla. Insurgents reported Spanish troops around Las Guasimas, who were a potential threat to the beachhead. While Brig. Gen. Young led a reduced brigade up the main road, the Rough Riders led by Col. Wood marched on a nearly parallel trail to the west. The two routes converged near the Spanish positions. At around 8:00am the American troops ran into the forward Spanish positions, and a confused firefight ensued. Young sent for reinforcements and used light artillery and machine guns to dislodge the Spanish from a fortified hilltop position which dominated the main road. The Rough Riders spread out to the east and west, linking up with Young’s column. The American line slowly pressed forward through two successive Spanish lines. As Gen. Wheeler arrived with reinforcements, the Rough Riders took a third Spanish position in a charge. The Spanish withdrew through Sevilla to Santiago, and the disorganised Americans remained on the battlefield.
When the former Confederate Gen. Wheeler saw the Spanish retreat, the old soldier forgot where he was for a moment, and shouted to his aides, ‘We’ve got the damned Yankees on the run!’ The American troops advanced and took the abandoned positions, but were too exhausted to pursue. As reinforcements arrived, they were pushed a half-mile ahead of the advance guard, giving Young’s men a chance to recover.
Further to the west, the Rough Riders were still trying to advance. The Volunteers moved forward in a series of rushes, and each tree line became a small battleground. Within 30 minutes of the first shots the Spanish had been driven back 300 yards; but the cost was high. The score of dead or wounded included Capt. Capron and Sgt. Hamilton Fish. As Spanish fire weakened it became clear that they were falling back all along the line, and the American line followed.
Around 8:00am a second Spanish defensive line was encountered, screened by a line of vines and branches. It was at this point that Edward Marshall of the New York Journal was hit, one of two civilians who received a commendation in the official despatches after the battle. The Spaniards fell back after a brief exchange of shots, and as the jungle opened up into increasingly large areas of tall grass, the Americans found the ground began to slope uphill. Ahead lay a large clearing, and at its far edge lay a tree line and a ruined distillery building, 200 yards from the American line. A flurry of shots showed that the tree line formed part of a major Spanish position. The distillery building became the focal point of the attack.
Naval launches landing troops and supplies on the new beachhead at Siboney. Despite a constant surf, this was chosen as the principal American supply base. (National Archives)
Spanish soldiers at Santiago de Cuba. The Americans were contemptuous of their opponents until they met them in combat. The Spanish performance at El Caney demonstrated the skills of the individual Spanish soldier. (National Archives)
Until this point the terrain had forced the Rough Riders to break into small groups. On the edge of the field Wood and Roosevelt organised their regiment, with the two senior officers stationed at either end of a line. It is unclear whether Wood or Roosevelt ordered the regiment to advance, or whether it resulted from a spontaneous movement by the rank and file. A reporter commented that Wood was calm under fire, but that Roosevelt ‘jumped up and down’ with eagerness. The advance was subsequently christened ‘Wood’s Bluff’, as the Spaniards thought the Rough Riders were the skirmish line of a much larger force. The line ran into the field, cheering as it advanced. The Spanish opened up on the attackers with a succession of disorganised volleys, causing several casualties. Their fire was insufficient to halt the attack, and as they approached the Spanish position the American cheer grew to the pitch where it was subsequently compared to the ‘Rebel yell’ of the Civil War. The Spaniards broke and ran back through the trees in confusion. The Rough Riders lay around the building awaiting orders.
One Spanish witness said: ‘When we fired a volley, instead of falling back they came forward. This is not the way to fight.’ Another Spaniard reported to his officers that ‘they tried to catch us with their hands’. The Rough Riders had come through their baptism of fire relatively unscathed. Of the 534 men in the unit, eight were killed and 34 wounded. Young’s column of 464 men had eight men killed and 18 wounded. The Spanish made light of the skirmish, and on 25 June the Espagna, a Santiago newspaper, even reported that ‘the column of Gen. Rubin … was attacked yesterday afternoon. This morning large forces of the enemy with artillery attacked said column anew. Their attack was made with vigour, and they fought without being under cover. They were repulsed with heavy losses’. Another Spanish report claimed that 4,000 Spaniards were attacked by 10,000 Americans, and the attackers suffered 265 casualties. In reality, the first battle of the war was nothing more than a confused and bloody skirmish. 1,500 Spaniards had been attacked by 1,000 Americans and been driven from their positions. The main American force was still disentangling itself from its beachheads, and its commander was completely unaware that a battle was being fought.
Cuban insurgents watching the Americans set up camp at Siboney. The guerrillas made a poor impression on the Americans, and observers complained of their lack of military enthusiasm. (National Archives)
Buffalo Soldiers of the US 10th ‘Negro’ Cavalry Regiment, photographed on San Juan Heights. Although misguidedly criticised by Roosevelt, other observers described them as ‘some of the bravest men I know’. (National Archives)
THE AMERICAN ADVANCE UP THE CAMINO REAL
The American troops earmarked for the assault on San Juan Heights rose soon after dawn on 1 July 1898. They had spent the night in bivouacs strung out along the road between El Pozo and Sevilla. As the Camino Real narrowed, the initial four-deep column was reduced to a line only two abreast. As the lead troops passed through El Pozo settlement, the nearby artillery battery fired, bringing down counter-battery fire. Shells fell beside the column, killing a number of soldiers. As the troops continued down the road they came under Spanish rifle fire, both from the troops on the Heights and from sharpshooters hidden in the woods. Since the Spanish Mauser rifle used a smokeless cartridge, the attackers remained hidden. An observation balloon accompanied the troops, tethered to a wagon that moved down the road with them. This did little but serve as a range marker for Spanish fire, and casualties mounted as the Spanish shells and bullets found their mark. Some of the heaviest American casualties of the battle were inflicted during the final stages of the approach march, and at the place where the road crossed the San Juan River. The shallow crossing was later dubbed the ‘Bloody Ford’.
The Spanish commander was reluctant to deploy his men too far in advance of his fortified positions around Santiago. Linares was still not convinced that the American landing was more than a diversion. Pulling his best troops away from Santiago would leave the city open to a second American landing or worse, a major attack by Cuban insurgents. Rubin achieved his limited objective of delaying the American advance, then withdrew back to the main perimeter around Santiago. Wheeler achieved his aim of clearing the way for the main army to advance on Santiago. Gen. Lawton, the designated leader of the V Corps advance, was furious with Wheeler for stealing the glory, but the old war-horse supplied the American public with the first victory of the war. The press considered that the American troops had been led into an ambush, but acclaimed the actions of the Rough Riders and Roosevelt. It was almost as if the regulars and Wood were merely supporting actors in a melodrama. This slant on press reporting was to continue throughout the campaign.
Gen. Shafter read the Spanish version of the skirmish, then quipped that: ‘reports from Spanish sources from Santiago say we were beaten, but persisted in fighting, and they were obliged to fall back!’ It was in fact a fairly accurate version of events at Las Guasimas.
During the afternoon of 26 June the Americans tried to take stock of their situation. Cuban irregulars, sent after the retreating Spanish, reported that there were now no Spanish troops between the American army and San Juan Heights, a mile outside the city of Santiago. Shafter ordered that Wheeler was to conduct no more ‘probes’, but was to entrench and hold the positions. Clearly he was unwilling to risk committing his army until all his troops were ashore and capable of supporting each other. The commanders on the field, Lawton and Wheeler, decided to interpret Shafter’s ordérs rather more loosely. Two miles ahead lay the village of Sevilla, where the road was flanked by the Aguadores River. This offered a better defensive position, and would be closer to Santiago when the time came to attack the Spanish again. That afternoon the Americans continued their advance to Sevilla and encamped around the village. Shafter had little option but to make this his base. For the next six days the army slowly gathered around Sevilla and hauled up supplies and guns along the grandly named Camino Real (Royal Road), described by some as being no better than ‘a mud slide’. Engineers worked on improving the road, laying ‘corduroy road’ sections of logs to try to keep the wagons out of the mire. As sentries guarded the positions and learned to tell the difference between nocturnal Spanish raiders and land crabs, the remaining soldiers rested in their bivouacs. On 27 June Gen. Shafter came ashore and set up his headquarters in the village.
Las Guasimas, the site of the first engagement between Spanish and American troops. This was the position on the track occupied by the head of the Rough Riders column when it ran into the leading Spanish outposts. (National Archives)
Sketch by Col. Leonard Wood, commander of the Rough Riders. The crosses show the forward Spanish positions at Las Guasimas, the hill taken by Gen. Wheeler and the battle line of the Rough Riders. (Monroe County Public Library)
Gen. Wheeler complained to Shafter that the positions around Sevilla were becoming too crowded, and asked for permission to advance a few miles up the road to El Pozo (‘the Fountain’), a low hill which was named after the hacienda lying at its eastern foot. After being issued strict instructions not to bring on another action, Wheeler advanced one and a half miles west to El Pozo, where he found himself overlooking the Spanish positions on San Juan Hill. To his left was the sea, hidden behind a hill. To his right were the foothills of the Sierra Maestra Mountains, and the village of El Caney. Ahead of him the Camino Real crossed the San Juan River: behind the river lay the San Juan Heights. One and a half miles from El Pozo hill, a Spanish blockhouse crowned the 150-foot-high ridge of the Heights. Slightly in front and to the right of this ridge was the smaller Kettle Hill, topped by a sugar refining ‘kettle’. Through a dip in the Heights the observers saw the outskirts of the city of Santiago. Spanish soldiers were visible on San Juan Heights and Kettle Hill, preparing a fortified line of trenches and barbed wire. Any attack would have to be launched soon, before these defences became impregnable. Cuban irregulars reported that an additional 500 Spaniards were fortifying the village of El Caney, to the north, which could pose a threat to any American advance on San Juan Heights as it lay on the American’s flank. Any move to outflank San Juan Heights would be impossible until El Caney had been captured. Other Cuban reports indicated that a relief force of several thousand men was approaching Santiago from the west. The attack had to be launched before these fresh troops arrived. Once the Americans held the Heights they could dig in and bombard the city until it surrendered.
The war correspondent Richard Harding Davis noted the activities of the Spanish: ‘A long yellow pit opened up in the hillside of San Juan, and in it we could see straw sombreros rising and bobbing up and down, and under the shade of the blockhouse, blue-coated Spaniards strolling leisurely about …’ In his report Davis went on to criticise Shafter for his inaction.
In the opinion of most Americans in the expeditionary force, time was on the side of the Spanish. Any delay would allow them to complete their fortifications, and to call in fresh troops from the surrounding countryside. Yellow fever and other tropical diseases would only further deplete American numbers and morale. The Americans were unaware, however, that the Spanish had their own problems.
When Shafter reached El Pozo he assessed the situation and realised that he would have to neutralise El Caney. Access to the north meant that he could improve links with the Cuban irregulars and possibly even cut off the city water supply, which ran by pipe south from the Sierra Maestra Mountains. One division would take no more than a couple of hours to clear El Caney. During that time the rest of the army would advance and deploy for an attack on San Juan Heights. The El Caney division could then attack the Heights from the north-east just as the main army launched a frontal attack on the Spanish defences. The defences could be rolled up from north to south before nightfall.
Gen. Shafter returned to Sevilla and began drawing up orders for the attack, which would be launched the following day, Sunday 1 July 1898. Gen. Lawton’s 2nd Division was to march off to the north immediately, and bivouac overnight just short of El Caney. The following morning Lawton would attack the village using all three of his brigades and a supporting artillery battery. The First Division and the Cavalry Division would move forward to El Pozo and wait for orders to attack the Heights the next day. A second artillery battery was ordered to deploy on El Pozo hill, where it could fire on the Spanish positions. At around 4:00pm, Lawton’s men began moving out of Sevilla. Battle was about to be joined, the first major action fought by an American army since April 1865.
Bodies of two dead Rough Riders lie in a clearing, while senior officers hold an impromptu conference behind them. The regiment lost eight men at Las Guasimas. (Franklin D. Roosevelt Library)