The Roughest Riders (2 page)

Robustiano Rivera
, the lighthouse keeper in Guánica.

Theodore Roosevelt
, the assistant secretary of the navy during the McKinley administration who later became the leader of the Rough Riders and president of the United States.

William T. Sampson
, the naval captain who led the first inquiry into the sinking of the USS
Maine
and was afterward promoted to rear admiral in command of the United States' North Atlantic Squadron.

William R. Shafter
, the elderly commanding general of US forces in Cuba who had himself fought for the North during the Civil War.

Theophilus Gould Steward
, the chaplain and only black officer with the Twenty-Fifth Infantry Regiment, the first troop ordered to war in Cuba.

José Toral
, the Spanish general who replaced General Linares after the latter was wounded in battle.

Harry S. Truman
, the president of the United States whose executive order integrated the US armed forces in 1948.

Joaquín Vara del Rey y Rubio
, a Spanish general who was killed in action while defending the village of El Caney against the American assault.

Pancho Villa
, the Mexican revolutionary who eluded attempts by the US government to capture him after he and his men raided a New Mexico border town.

Joseph “Fighting Joe” Wheeler
, an aging Confederate veteran of the Civil War who served as a general in command of Buffalo Soldiers in Cuba.

Charles A. Wikoff
, the colonel who led a unit of Buffalo Soldiers up San Juan Hill and there became the most senior-ranking American officer killed in action to that date.

Woodrow Wilson
, president of the United States during World War I and openly hostile toward racial equality in the military.

Leonard Wood
, a colonel and medical doctor, the head of the First Volunteer Cavalry, and the original leader of the Rough Riders.

Charles Young
, the third African American graduate of West Point, who was also a captain during the war in the Philippines and a major during the search for Pancho Villa in Mexico.

Samuel B. M. Young
, a general who was the second-in-command to General Wheeler.

L
ieutenant Colonel Theodore Roosevelt was worried about the condition of some of his men. They were cavalrymen, not foot soldiers, and this narrow path through rugged terrain required special stamina. Most of his Rough Riders were volunteers, cowboys used to making their way on horseback over flat western desert and prairie land, yet here they were, on hilly trails sometimes facing brush so thick they had to pass through it single file. Roosevelt, on horseback himself, led his men along the rugged wagon road following the coast. The day before, several hundred white and black soldiers had bushwhacked the trail under nearly impossible conditions.

Another column of soldiers, consisting of both all-white and all-black regiments, had blazed its own route through thick foliage a few hours before Roosevelt's Rough Riders started out. The grueling path wound precipitously along the coast, causing some of the troops to stretch out like an accordion behind the men plowing on before them. One soldier later said, “They advanced as blind men would through the dense underbrush.” They continued their sluggish pace for five arduous miles toward Siboney, their first stop along the shoreline. The combined US forces that had landed so far totaled about a thousand.

Roosevelt urged his men to follow him as closely as possible as he rode ahead to catch up with the others in Siboney. The Cuban summer heat was unbearable, even as twilight approached; it had taken them all afternoon to navigate less than five miles under the worst conditions imaginable. The heavy loads the men carried on their backs made the temperature and humidity almost unendurable.

Roosevelt and his Rough Riders finally arrived the evening after the first column of soldiers had made camp. He ordered the men to rest as much as possible, in preparation for launching an assault on the well-fortified Spanish positions up in the hills. They bivouacked in a torrential downpour that lasted for hours near the dismal coastal village of Siboney, at the edge of the Caribbean just east of Santiago de Cuba. When the rain let up, the men fried pork and hardtack and washed it down with bitter coffee. Roosevelt had orders to set off at daybreak with the other regiments and make their way uphill toward Las Guasimas, a settlement located at the junction of two mountain passes. The Spanish had fifteen hundred or more regular army troops in place, with orders from General Arsenio Linares to hold off the Americans.

The Spanish soldiers had superior weaponry at their disposal. Most were armed with 7mm Mauser rifles with repeating bolt action, high-velocity cartridges, and smokeless powder. Supporting them from behind was an impressive array of artillery that could cut through trees and bring an avalanche of fallen timber down on the Americans' heads. The Rough Riders and the other American troops carried more outdated equipment—smaller .30 caliber Krag-Jørgensen rifles and carbines, and Springfield rifles with carbon-powder charges that emitted black smoke and revealed the troops' positions. Their artillery consisted of a four-gun detachment of older hand-cranked Gatling and Hotchkiss guns. Roosevelt moved forward and the American soldiers followed in his wake.

The Americans opened fire first, and the Spaniards responded with their rapid-fire rifles and artillery. The US guns filled the air with billowing dark smoke, while the Spanish weapons gave off no smoke of their own, making their emplacements hard to pinpoint. The Americans advanced blindly into the face of the whizzing bullets and cannonades raining down on them. Their noses filled with acrid smoke, their eyes burned like fire, and their ears rang with the deafening pounding.

Then tree limbs came crashing down and the American troops started to drop around Roosevelt, who continued his upward advance. Men were tumbling like bowling pins, some struck in the head, others in the groin and legs. Roosevelt was hit indirectly himself when a bullet smashed through a palm tree and showered him with splinters and wood dust. The sounds, smells, and taste of war smothered everything. The fighting raged for a couple of hours, and Roosevelt's Rough Riders were struck especially hard, as they were in the lead now and were in danger of being completely cut down in their tracks.

Despite the chaos, US troops eventually prevailed against the Spanish defenses at Las Guasimas, the first battle in Cuba, thanks mostly to the intervention of black troops who prevented the Rough Riders from being wiped out. It would not be the last time black soldiers would come to the rescue. The Spaniards, meanwhile, pulled back and formed new perimeters a few miles farther uphill. One line of defense was at Kettle Hill, a second was strung along San Juan Hill, a bit to the south. Both positions would eventually be taken, but first came the major struggle in the miserable village of El Caney, a mountain town to the north.

A week after the Battle of Las Guasimas, the order came for the Americans to capture El Caney and the two major hills in the cradle of land known as the San Juan Heights. After a bloody day-long battle, American forces eventually overran El Caney thanks largely to the all-black Twenty-Fifth Infantry Regiment. Roosevelt was assigned to focus the Rough Riders on Kettle Hill, situated between San Juan and El Caney. There, Roosevelt's troops came under heavy fire from the Spaniards, who were laid out along the crest, ensconced in hand-dug trenches that kept them shielded from—yet gave them a somewhat truncated view of—approaching hostile forces. Other Spanish troops were well hidden behind stone barricades and inside blockhouses that provided good protection against the advancing Americans.

Roosevelt attempted to put his Rough Riders in the lead, but he and his men had trouble keeping up with the regulars of the all-black Tenth Cavalry, under the command of Captain John “Black Jack” Pershing. Together, they pushed on through blistering enemy fire, taking heavy losses as they slogged uphill. In general, the Spaniards occupied well-concealed positions, although they were not entrenched in what the Americans would have considered the most advantageous locations. Had it been them defending the hill, they would have placed most of their troops along a lower promontory on Kettle Hill—the “military crest”—a hundred yards or so below the geographical peak. That would have given the defenders a more commanding view of the downward slope, providing them a clear, unobstructed line of fire. Still, there was little question that the enemy had the advantage, lying in trenches as the Americans climbed under great duress.

The Spanish continued to unleash all their firepower, inflicting mounting losses on the Americans. Near the brink of disaster, the attackers managed to maintain their forward momentum and suddenly became invigorated by the sight of the Spanish flag on the
crest. The all-black regiments, including Pershing's Tenth and the black Ninth to their left, charged past the Rough Riders toward the clearing near the top, lacing the air with chilling battle cries they had learned in earlier wars. They ran ahead furiously and courageously, seemingly without regard for their own lives and safety. The specter they created took the Spaniards by surprise and shocked them with the sheer ferocity of the attack. The Spanish gave way, some throwing down their weapons while others broke and ran down the paths leading southward toward San Juan Hill.

Roosevelt's Rough Riders followed the black soldiers to the peak as the Spaniards streamed down the far side of the hill. But Roosevelt had been delayed a moment earlier when his horse became ensnared in a barbed wire barricade, halting his progress and forcing him to climb the rest of the way on foot with his remaining men struggling up behind him. Once there, the Americans stormed together over the abandoned Spanish fortifications, unable to believe that they had prevailed in the face of what looked like certain annihilation just minutes before. Kettle Hill was theirs now, totally vacated by enemy troops except for the dead and wounded.

The Spanish fled as fast as they could toward San Juan Hill, occasionally turning to attempt resistance, showering their pursuers with a fusillade of bullets and shells, but there was no reversal of their broad retreat. The Americans, meanwhile, were too exhausted after the arduous climb to follow them. With rifles that had been thrown aside by deserting Spaniards or retrieved from the wounded enemy soldiers left behind, they fired with relish at the retreating troops, now in open disarray.

But the battle for San Juan Hill itself was still in progress, with five thousand American troops engaged in the action, including the Buffalo Soldiers of the Twenty-Fourth Infantry, who had made the climb from Siboney and another hill called El Pozo. Black and white soldiers from three different brigades launched their own attack on
San Juan Hill, with the Twenty-Fourth leading the way. There, too, they overcame enemy resistance after hours of bloody combat. As they swarmed over San Juan Hill, they could see the Spaniards running as fast as they could down every path available to them. It was all over now, except for the final mopping up, which would include the conquest of the main Spanish fortifications around the city of Santiago de Cuba.

The air stank with blood, burned flesh, and spent shells. Roosevelt strode among the wreckage and counted the dead and wounded. The army's official tally of those who fell in battle was far smaller than the number of casualties reported by eyewitnesses to the action; the pantheon of black and white men who lost their lives or were wounded fighting with Roosevelt's Rough Riders was much larger than first reported. The popular press also perpetuated inaccuracies regarding the battle itself, claiming Roosevelt and his volunteers chased the Spanish from San Juan Hill virtually unaided, when the reality was that they did not even make it into the thick of battle until most of the heavy fighting was over.