The Roughest Riders Read online

  Around dawn, the order came for the first column of men, including the Buffalo Soldiers of the Twenty-Fifth, to leave immediately and push along on the path to Siboney. The black Ninth and Tenth stayed behind with Wheeler’s forces, also serving under his second-in-command, General Samuel B. M. Young. The Twenty-Fifth and some white units marched single file on the unpaved trail, with orders to hook up with the black Twenty-Fourth under General Jacob Kent after they landed. The Twenty-Fifth and their white compatriots left almost as soon as they hit the beach and made first camp around 8:30 that evening.

  “We marched about four and a half miles through the mountains; then we made camp,” a black soldier with the Twenty-Fifth wrote later. Another with the same outfit wrote, “A short distance ahead (from the shore) we bivouacked for the night. We were soon lying in dreamland, so far from friends and home, indeed, on a distant, distant shore.”

  A white staff officer described the movement similarly in his own account of the action: “General Lawton, with his Division, in obedience to this order, pushed forward from Daiquiri about five miles, when night overtook him and he bivouacked on the road.” The campsite was a brush-covered flat with heavy jungle growth on one side and a shallow, stagnant pool on the other. The men dined on canned meat and beans heated on open fires; hardtack; and coconuts and chili peppers they found in the area, all washed down with coffee made from river water.

  The rainy season had arrived, making the going more treacherous as the men slogged over muddy trails beneath dripping canopies of trees. The land crabs returned, their appetites for carrion intensified with the advent of the steady tropical downpours, turning them into even more formidable adversaries than the men had first thought. The Spanish proved to be less of a problem, offering only token resistance at Siboney, which the first column of Americans occupied on the morning of June 23. Shafter had instructed Lawton to remain there while the rest of the supplies were being unloaded onto the beach at Siboney, now that his troops were in control there.

  Wheeler and Roosevelt fumed at being left behind at the Daiquiri campsite to guard against any possible Spanish rearguard assault. Each of them had trouble containing his urge to be in the middle of the fighting, one to enhance his military career and the other his political one. Fighting Joe decided to take action on his own, defying Shafter’s orders. He left Daiquiri with a squad of scouts early on June 23, and Young followed closely behind with some white regulars and some black soldiers from the Ninth and Tenth. Wheeler infuriated Roosevelt all the more with his order for Roosevelt to stay behind with his band of Rough Riders.

  Wheeler was surprised to see that the Spaniards had not defended the route to Siboney at several locations where they could have had a distinct advantage over the Americans grinding their way along the trail. Lawton was almost speechless when he saw Wheeler and his scouts tromping unannounced into his campsite. Wheeler informed Lawton that he had learned from Cuban rebels on the way that Spanish forces lay well entrenched at a fork in the trail three or four miles inland. Wheeler wanted to march uphill and assault the position directly, but Lawton viewed the situation differently. Lawton preferred to take a more circuitous route along the seacoast and attack the Spanish flank, forcing them toward Santiago at the risk of being cut off from their main line of defense. The two generals stood there at loggerheads, one obeying his commander’s orders, the other in open defiance of them.

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  General Shafter sat hobbled by gout on his ship, observing the activity on the coast the best he could through field glasses. Richard Harding Davis, a reporter for the New York Herald, vividly captured the scene during the landing:

  It was one of the most weird and remarkable scenes of the war, probably of any war. An army was being landed on an enemy’s coast at the dead of night, but with somewhat more of cheers and shrieks and laughter than rise from the bathers in the surf at Coney Island on a hot Sunday. It was a pandemonium of noises. The men still to be landed from the “prison hulks,” as they called the transports, were singing in chorus, the men already on shore were dancing naked around the camp fires on the beach, or shouting with delight as they plunged into the first bath that had been offered in seven days, and those in the launches as they were pitched head-first at the soil of Cuba, signalized their arrival by howls of triumph. On either side rose black, overhanging ridges, in the lowland between were white tents and burning fires, and from the ocean came the blazing, dazzling eyes of the search-lights shaming the quiet moonlight.

  For his part, Shafter sat immobilized by his throbbing foot and the oppressive heat and humidity bearing down on him. He tried to make what sense he could of the men milling about on the shore, but he couldn’t be sure which troops were Lawton’s and which were Wheeler’s amid the chaos. His mood was soured all the more by the lack of communication from his men on land.

  The place that lay a few miles uphill at the crossroads was called Las Guasimas, named for the fruit-bearing trees that adorned the hill. Before the Spanish had chased them out, the locals used to pluck the fruit and feed it to their pigs. Richard Harding Davis, one of the handful of writers who reported from the scene, depicted the site as “not even a village, nor even a collection of houses.” Two trails came together there, forming the apex of a V. The site was located about three miles inland from Siboney. From the point where they met, the trails merged and continued along a single trail toward Santiago. General Wheeler took it upon himself to reconnoiter the area in the company of some Cuban rebels. He declared openly that he intended to attack Las Guasimas in the morning, whether Shafter authorized it or not.

  While Lawton and Wheeler debated military strategy, Roosevelt sat stewing with his Rough Riders on the beach in Daiquiri. They glumly ate a lunch of bacon and beans while Roosevelt reined in his urge to get moving along the route Wheeler had taken earlier. Finally, at 1:30 in the afternoon of June 23, Colonel Wood told Roosevelt that he received an order from Wheeler for the Rough Riders to strike out along the coast toward Siboney. In addition to a supply of rations, they planned to carry with them an assortment of picks, shovels, and other equipment that would come in handy for digging trenches. Their mule train was reduced to 16 animals from the 189 they had started with in San Antonio; some had been left behind in Florida, and others never made the swim to shore. But before they got under way, Wood decided to leave the slimmed-down mule train with all the equipment in Daiquiri to speed up their journey. They compensated by taking with them some extra first-aid kits instead.

  The Ninth and Tenth black cavalry saved the Rough Riders from extermination at Las Guasimas, about three miles inland from the coast. Roosevelt was injured in the battle, and several of his top aides lost their lives.

  Library of Congress Prints and Photographs Division (LC-USCZ4-508)

  The men trudged awkwardly along the crude trail, except for Wood and Roosevelt, the latter furious that he had to ride his one remaining horse bareback “like an Indian.” New York Journal correspondent Edward Marshall recalled that Roosevelt’s “wrath was boiling and his grief was heart-breaking.” Somehow, Marshall’s saddle had made it to shore even though his own horse had remained behind, so he lent Roosevelt his saddle to relieve his distress.

  After Wood, Roosevelt, and company got started, their aging surgeon and medical officer, Major Henry LaMotte, decided to disobey orders and follow them with the mules, which he had laden down with additional medical supplies. He led the pack riding bareback on one of the mules to ease the pain of an ankle he had sprained. The going was slow and difficult, but he was determined to make sure the troops had ample medical supplies, including surgical implements he would need in the event of inevitable injuries. The line of men and mules stretched farther out along the path as the various units moved ahead at an uneven pace, the better-conditioned pushing ahead to the front of the group while the cavalrymen, unused to long hikes, fell to the rear.

  Well ahead of them all was Wheeler, who had lost patience with Lawton and took it upon hims
elf to plan military strategy with his subordinate, General Young, and with Colonel Wood, once he arrived. Young would do Wheeler’s bidding no matter what, and Wheeler felt that Wood—and Roosevelt in particular—would be more agreeable to an aggressive military action than the overly cautious Lawton. He also mistakenly included in his plans one of the Cuban rebel leaders whom he had encountered in the area: an unsavory character and possible turncoat who called himself General Castillo.

  Each man with Wood and Roosevelt carried on his back a blanket roll, one hundred rounds of ammunition, and his weapons. They stuffed whatever rations they could into haversacks and the pockets of their uniforms, and a few others slung entrenching tools and axes on straps across their chests. The ground was rocky and soggy, making the footing all the more hazardous with the heavy loads. The path they traveled was sarcastically labeled El Camino Real—The Royal Road. Like the others who had passed before them, they pushed along in single file since the path was not wide enough for two men to walk abreast. It was rutted with wagon tracks that turned into streams of flowing mud during a torrential downpour, something that occurred every day this time of year. The heat and humidity were unbearable, and the men sweltered all the more beneath the weight of their heavy, sodden uniforms. The thick jungle growth pressed in on them from all sides, snagging their packs and rifles as they pressed on toward Siboney.

  Before they reached the village, they came across a wide stream flowing with clear water up to their shins. Wood sent word back to the men straggling behind that they could stop and fill their canteens if they took care not to stir up the mud from the bottom. But no sooner had they topped off their canteens than they heard the sounds of laughter and splashing farther upstream. Young had arrived earlier with the other troops in Wheeler’s command, including the black soldiers with the Ninth and Tenth, who were stripped down to their skivvies, some bathing, others pissing in the stream. The Rough Riders were so outraged by the sight of the cavorting black troops, who were apparently bearing up far better than they were under the ordeal, that they cursed them loudly and made a show of dumping the water back into the stream.

  It wasn’t long before they began to discard more than water. Men were falling by the wayside sick with exhaustion and heat prostration. Many tossed off their bedrolls, haversacks, cooking utensils, picks, and shovels in an effort to lighten their loads. Roosevelt, still on horseback, fell back through the ranks to urge his men forward. Some staggered to their feet in a heroic effort to reach their destination. As Roosevelt rode along, he saw that some of his troops had even abandoned their food rations—mostly heavy cans of meat, potatoes, and tomatoes. They all continued along the path, hoping to rendezvous as soon as possible with the black Twenty-Fifth and the white regulars, who had been the first to march to Siboney with Lawton. Wood rode ahead with a few of the men after urging Roosevelt to do what was necessary to get the men into camp in good condition.

  To his credit, Roosevelt admitted that the journey was easy for him since he was on horseback, while his men had to slog along on foot.

  PART TWO

  The Hills

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  Wood reached Siboney ahead of his troops, and there he encountered Fighting Joe Wheeler at 7:30 in the evening. Wheeler, with Young and Castillo by his side, informed Wood that there was a Spanish encampment on a hill a few miles inland and he intended to take it by force with or without Lawton’s consent—or Shafter’s, for that matter.

  Lawton was still in denial, refusing to believe that Wheeler would flout his commanding general’s orders and take such action on his own. Young, as Wheeler expected, rubber-stamped his boss’s decision, saying, “General Wheeler, give me permission to go out there.” Wood, too, offered no resistance to Wheeler’s plan. Lawton finally got the message that Wheeler had stacked the deck against him and “was scheming to leave him in the lurch and have a fight.” Roosevelt rode into camp about 9 PM, with most of his men trudging in after him. He ignored Lawton and immediately joined forces with Wheeler and the others, expressing his own desire to move against the Spaniards.

  Lawton tried to get word of what was transpiring to Shafter, who was still incapacitated on the Seguranca and wondering what was happening on shore, but a storm had kicked up, roiling the seas and making it impossible for a lifeboat to traverse the three miles out to Shafter’s vessel. So Shafter sat anchored in the dark, except for the bright searchlights that illuminated the shore, where the men danced on the beach around their campfires. Night had fallen like a shroud on the overhead cliffs.

  Along the coast in Siboney, Lawton tried frantically to stop Wheeler from launching his unauthorized military operation. Wheeler planned to attack Las Guasimas early the next morning, June 24, but Roosevelt’s men appeared incapable at the moment of making the grinding uphill climb with only one night’s rest. They threw themselves onto the ground, making camp on a bluff overlooking the sea. Most of them were exhausted and dehydrated, suffering from blistered feet and painful insect bites. But their spirits rose when they realized that they were almost within shooting distance of the enemy. They lit fires and broke out what rations they had left, mostly bacon and hardtack. Troops from the black Tenth had found some sweet Spanish wine alongside the path, which they willingly shared with Roosevelt’s men. For the moment, all animosity between the black and white soldiers had faded. They were soon to be comrades in arms, risking their lives in combat on foreign soil.

  While one batch of soldiers rested in camp awaiting orders for the next move, the transport ships managed to brave the churning water and land additional troops on the beach at Daiquiri. Not all of them made it through the dangerous waters onto land, and the operation was halted when the fury of the storm intensified, blasting the entire coastline with howling winds and driving rain. The downpour doused the campfires and saturated the blanket rolls and equipment, turning the night into a vortex of water and wind. The men gave up all hope of staying dry. They wolfed down the remains of their soggy food and curled up on the muddy ground in a fruitless effort to get some sleep. The pounding rain lasted about an hour before it rolled farther inland, leaving the invaders wet and cold as the pitch-black night closed in around them.

  Wheeler told Young and Wood to be ready to attack Las Guasimas before daybreak. But it would be a long, uncomfortable night before dawn tinted the sky. The men had difficulty falling asleep until after midnight. When the rain stopped, Roosevelt scouted the area with his close friend Sergeant Hamilton Fish and Captain Allyn Capron Jr., Wood’s third-ranking officer after Roosevelt. Both Fish and Capron had intimations of their own mortality in the hours before the battle.

  The layout of the land east and north of Santiago de Cuba, with the major hills and battle sites spread throughout the region.

  Based on a map that appeared in San Juan Hill 1898 by Angus Konstam, Osprey Publishing, 1998.

  “It would be my luck to be put out now,” Fish told Roosevelt.

  “Well, by tomorrow at this time the long sleep will be on many of us,” Capron muttered with a similar sentiment.

  Major LaMotte rumbled into camp around 3:00 AM with his mule train and medical supplies, waking up most of the men, including Wood and Roosevelt. Wood had called for reveille at 4:00 AM, and he didn’t appreciate having his rest disturbed by a lower-ranking officer, much less one who had disobeyed his orders to leave the mules in Daiquiri. He ordered LaMotte to unload his supplies, establish a base hospital, and stay put in Siboney. Wood was happy enough to have the mules available, however, and he ordered his men to rope their weapons around the sixteen mules LaMotte had brought into camp. Roosevelt’s displeasure with LaMotte was more pronounced than Wood’s; if LaMotte was going to disobey orders and bring the mules to Siboney, he should at least have had the foresight to carry dry bedding for him and the rain-soaked troops. LaMotte suffered Roosevelt’s wrath in silence. “He seemed to think … that I should have selected his bedding,” he said afterward, “but as I had not brought a stitch of bedding or clothing m
yself, I didn’t think he had any right to complain.”

  Now that he was awake, Wood let Captain Capron in on the morning’s plan of attack, and Capron volunteered to lead the Rough Riders up the trail. Wheeler intended to send Young up the main road with two squadrons of white and black troops, the First and Tenth regulars, and have Wood and Roosevelt march a column of Rough Riders up a steeper mountain path to their left. The combined American forces totaled approximately one thousand men—including about five hundred Rough Riders—taking on what proved to be less than half the number of the Spanish defenders they expected to encounter.

  The men relit the fires and ate a breakfast of bacon, canned tomatoes, and hardtack fried in bacon grease a little after 4:00 AM. Some had a handful of coffee beans, which they smashed with rocks and boiled in river water. Others discovered a cache of Cuban rum, which they poured into their canteens to fortify themselves before the onset of battle. The troops were ready for whatever came next.

  Six leading reporters of the day, including Richard Harding Davis, Edward Marshall, and Stephen Crane, the author of The Red Badge of Courage who was writing for the World, had been chosen to cover the men as they charged before the Spanish guns. Others would join them later.

  Crane was particularly taken with the spirit of Captain Buckey O’Neill, who had tried to save the two black soldiers from drowning during the beach landing. “He was going to take his men into any sort of holocaust,” the great writer reported, “because—he loved it for itself—the thing itself—the whirl, the unknown.”