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President William McKinley, roused from a deep sleep by an aide at 2:00 a.m. on February 16, 1898, received terrible news. The battleship Maine had exploded in Havana harbor with heavy loss of life. McKinley, who had been gently ministering to the public’s war fever for more than a year, was stricken. ‘The Maine blown up,’ he mumbled over and over to himself. ‘The Maine blown up!’ He hated the thought of war to the core of his being. ‘I have been through one war,’ said the Civil War veteran. ‘I have seen the dead piled up, and I do not want to see another.’ This sentiment was shared by every member of his administration, save one.

As always, Assistant Secretary of the Navy Theodore Roosevelt was up early that morning, and working in his office in the Navy Department on Sixteenth Street. ‘I would give anything if President McKinley would order the fleet to Havana tomorrow,’ ‘T.R.’ wrote to a friend. ‘This Cuban business ought to stop. The Maine was sunk by an act of dirty treachery on the part of the Spaniards, I believe; though we shall never find out definitely, and officially it will go down as an accident.’

He was certainly correct about the latter. A naval board of inquiry concluded that the Maine had been destroyed by a submarine mine of unknown origin. Predictably, Spain issued a report stating that the cause of the explosion had been internal. Americans who did not work in the White House or on Wall Street thought little of such formal deliberations. They only cared that 260 American sailors were dead, and they wanted a reckoning.

That day of reckoning was at hand, for the rusted, antiquated Spanish empire had prolonged its existence for far too long. It was not the sinking of the Maine, not the rantings of the yellow press, nor the jingoistic dreams of American imperialists that brought on the war of 1898 — it was the incredible incompetence, myopic short-sightedness, and stunning brutality of the Spanish imperialists in Cuba that made conflict inevitable.

A string of cruel acts in Cuba had enraged Americans for more than a generation. In 1873, five years into a Cuban uprising, a Spanish warship captured the American steamer Virginius as it attempted to deliver guns, ammunition, and medical supplies to Cuban patriots. Four rebel leaders aboard the Virginius were subsequently shot, decapitated, and their heads displayed on pikes. Captain Joseph Fry and 48 of his crewmen were summarily executed by firing squad. Spain reluctantly released the survivors of the Virginius and paid a small indemnity, but the bloody incident was not forgotten in the United States.

In April 1895, the cry of ‘Cuba Libre!’ again resonated across the island. Spain responded to this latest revolt by sending General Valeriano Weyler y Nicolau to Cuba. Dubbed ‘Butcher Weyler’ by the New York press, his scorched-earth policy devastated eastern Cuba and led to the deaths of thousands of civilians in concentration camps. The Spanish seemed intent on breaking the Cuban people in a desperate bid to continue the pretense of their position as a world power. In America, President Grover Cleveland was stridently against intervention. He could take solace as he left office in March 1897 that his successor, William McKinley, held similar views. The business interests in the country adamantly opposed war, as did most of the leading men in Congress. When the Spanish government recalled Weyler and granted more autonomy to Cuba it seemed that the crisis might pass.

Yet nothing could silence the Cuban cry for freedom. By 1897, Cuban rebels were even appearing nightly in ‘Buffalo Bill’ Cody’s Wild West extravaganza as part of his ‘Congress of Rough Riders of the World.’ The press exploited every Spanish atrocity, real or imagined, to full effect. The American people fumed with indignation over Cuba, idealizing the insurgents as soulmates of the American revolutionaries of 1776. Their slow-burning anger needed just a spark to explode in rightful wrath. The Maine was that spark. Poet Richard Hovey gave them their call — ‘Ye who remembered the Alamo, Remember the Maine!’ — and as it became their byword, action became their creed.

War advocates had their man in the 39-year-old Roosevelt, who had worked hard for a year to improve the navy. Now, as the days passed, he became nearly frantic over the administration’s continuing inactivity. President McKinley, T.R. grumbled to a confidant, ‘has no more backbone than a chocolate eclair.’

Roosevelt, although liked and respected by both McKinley and Secretary of the Navy John Long, found himself increasingly isolated within the administration and the Republican Party. The president would no longer see him, while Long simply humored him. Roosevelt found solace in his correspondence and talks with influential expansionists such as Senator Henry Cabot Lodge, naval officers Alfred Thayer Mahan and George Dewey, and, most importantly, army Captain Leonard Wood.

Wood and Roosevelt had met the previous June, and their jingoistic sensibilities and mutual love of football and vigorous walks led to an instant and warm friendship. A New Englander, Wood was a Harvard graduate like Roosevelt, having received an M.D. in 1884. Bored with private practice, he had gone west, hiring on as a contract surgeon with the army in Arizona and winning high praise (and eventually the Congressional Medal of Honor) for his heroic service during the campaign against the Apache leader, Geronimo. Promoted to captain and assistant surgeon in the regular army in 1891, Wood was transferred to Washington, D.C., four years later.

In the nation’s capital, Captain Wood was appointed assistant attending surgeon, giving him medical responsibility and unlimited access to high-ranking military officers, the secretary of war, and the president. He became close to President William McKinley, who placed his faith in Wood’s skill and compassion in treating Mrs. McKinley, who suffered from epilepsy.

When Roosevelt came to Washington in the spring of 1897 as assistant secretary of the navy, he found himself somewhat in awe of Captain Wood. ‘It was a pleasure to deal with a man of high ideals,’ he wrote, ‘who scorned everything mean and base, and who also possessed those robust and hardy qualities of body and mind, for the lack of which no merely negative virtue can ever atone.’ They were, in every way, kindred spirits.

Mckinley made a last ditch effort for peace, demanding that Spain declare an armistice in Cuba as of April 1, 1898. The Spanish government hesitated, then finally agreed to end the fighting on the island and to submit the Maine question to arbitration. Only the question of Cuban independence reMained. By then, however, it was too late. On April 11, 1898, McKinley asked Congress to intervene on behalf of Cuba. On April 19, the Senate and House of Representatives passed a joint resolution calling for American armed intervention to secure Cuban independence, while disclaiming any designs on annexing the island. On April 23 Spain declared war on the United States, who reciprocated two days later.

McKinley called for 125,000 volunteers to augment the 28,000-man regular army. Young men from every section of the country rallied to his call. They were anxious to prove themselves equal to the task and worthy of their place as Americans. Among the first to volunteer was the man who had perhaps been the leading advocate for war — Theodore Roosevelt.

Everyone was astonished by this act. His wife, Edith, opposed it, as did best friend Henry Cabot Lodge. ‘Theodore Roosevelt,’ wrote diplomat John Hay, ‘has left the Navy where he had the chance of his life and has joined a cowboy regiment.’ Secretary of the Navy Long also fretted over this act of recklessness but foresaw that the great risk was not without potential reward. ‘He has lost his head to this folly of deserting the post where he is of the most service and running off to ride a horse and, probably, brush mosquitoes from his neck on the Florida sands,’ he confided to his diary, ‘and yet how absurd this will sound, if by some turn of fortune he should accomplish some great thing and strike a very high mark.’

President McKinley twice attempted to change Roosevelt’s mind, to no avail. ‘One of the commonest taunts directed at men like myself is that we are armchair and parlor jingoes who wish to see others do what we only advocate doing,’ declared Roosevelt. ‘I care very little for such a taunt, except as it affects my usefulness, but I cannot afford to disregard the fact that my power for good, whatever it may be, would be gone if I didn’t try to live up to the doctrines I have tried to preach.’

Included in McKinley’s call for volunteers had been an appeal for three regiments ‘to be composed exclusively of frontiersmen possessing special qualifications as horsemen and marksmen.’ Secretary of War Russell A. Alger offered command of the first such regiment to the administration’s only bonafide cowboy, Roosevelt, who had once operated a ranch in Dakota Territory. Roosevelt wisely declined because of his lack of military experience, suggesting that Leonard Wood be named colonel and that he go as second-in-command. Alger agreed.

The First U.S. Regiment of Volunteer Cavalry was to be recruited in the southwestern territories, with 340 men to be raised in New Mexico, 170 in Arizona, 80 in Oklahoma, and 170 from the Indian Territory. Within days of the sinking of the Maine, West Point graduate Alexander Brodie, a Prescott, Arizona, mining engineer, along with Phoenix journalist James McClintock and Prescott mayor William ‘Buckey’ O’Neill, had already begun recruiting volunteers.

The first to formally enlist was O’Neill, a frontier legend at age 38 and among the most popular men in Arizona Territory. Born in Ireland, he had come to Arizona in 1879. He was working as a journalist for the Tombstone Epitaph at the time of the O.K. Corral gunfight and soon had his own reputation for gunplay as the hard-riding sheriff of Yavapai County. His nickname came from his passion for faro, or ‘bucking the tiger’ in that frontier game. Dedicated to the cause of Arizona statehood, he was now prepared for the greatest wager of his life. ‘Who would not gamble,’ he wrote to a friend, ‘for a new star in the flag?’

Brodie secured an appointment as senior regimental major, with O’Neill and McClintock as company commanders. By May 4, 200 recruits were gathered in the Prescott plaza. Accompanied by Josephine, a rather ill-tempered young mountain lion given to the troops as a mascot by a local saloon owner, they boarded trains amidst much fanfare and set off for their San Antonio training station.

New Mexico Governor Miguel Otero wasted no time in recruiting troops and a remarkable corps of officers. Captain William Llewellyn of Las Cruces had been a federal lawman in Dakota Territory, famed for destroying Doc Middleton’s outlaw gang. Captain George Curry, the strapping former sheriff of Lincoln County, had known both Billy the Kid and Pat Garrett, while Captain Maximiliano Luna belonged to one of the most prominent Hispanic families in the territory. The New Mexico recruits reached San Antonio on May 10, joining the troops from Arizona and 83 men from Oklahoma raised by Captain Robert Huston of Guthrie. A week later, 170 more men arrived from the Indian Territory — including full or mixed-blood Cherokee, Choctaw, Chickasaw, Pawnee, and Creek Indians. Within days they were augmented by a remarkable contingent of about 50 well-to-do easterners. These Ivy League friends of Roosevelt included some of the best athletes and richest young men in America. The westerners initially viewed them with skepticism, and not a little contempt, but were soon won over.

‘These men are the best men I have ever seen together,’ Colonel Wood wrote to his wife, ‘and will make the finest kind of soldiers.’ Cowboys and polo players, teamsters and yachtsmen, lawyers and day laborers, lawmen and outlaws, miners and football players, Indians and Indian fighters formed a strange amalgam that forecast, in Roosevelt’s eyes, the new American century while harkening back to the old frontier. ‘Wherever they came from, and whatever their social position,’ he wrote, ‘[they] possessed in common the traits of hardihood and a thirst for adventure.’

Roosevelt did not arrive in San Antonio until May 15. He had remained in Washington to secure weapons, uniforms, and supplies for the regiment. The press had already dubbed the unit ‘Roosevelt’s Rough Riders’ — a name T.R. did not relish because of its obvious reference to Buffalo Bill’s Wild West show — and the men were anxious to see their namesake lieutenant colonel. Many were at first unimpressed with his somewhat comical appearance, but that quickly changed. Lieutenant Tom Hall sized him up immediately: ‘He is nervous, energetic, virile. He may wear out some day, but he will never rust out.’

Rumors abounded that Spanish Admiral Pascual Cervera’s Atlantic fleet was headed for either Puerto Rico or Cuba. On May 29, Commodore Winfield Scott Schley’s ‘Flying Squadron’ found Cervera moored in the harbor at Santiago de Cuba and set up a blockade. That same Sunday morning, the Rough Riders — 1,060 strong with 1,258 horses and mules — began boarding Southern Pacific Railroad cars for the journey to Tampa, Florida, their jump-off point for Cuba. ‘In all the world there is not a regiment I would so soon belong to,’ Roosevelt wrote to the president. ‘We earnestly hope we will be put in Cuba with the very first troops; the sooner the better.’

All was confusion in Tampa. Major General William Rufus Shafter, a Civil War veteran and former Indian fighter, was in command of the Fifth Army Corps. Weighing more than 300 pounds and afflicted with various ailments that did little to sweeten a notoriously foul temperament, Shafter was totally unfit to lead an expeditionary force into the tropics. In charge of his cavalry was the diminutive Alabama Major General Joseph ‘Fighting Joe’ Wheeler, famed Confederate cavalryman and current congressman. Ten regular and two volunteer cavalry regiments would be under his command. Despite his age and seeming frailty, Wheeler was as energetic and bold as Shafter was sloth-like and cautious. Brigadier Generals J. Ford Kent and Henry Lawton would command infantry divisions. In all, some 17,000 men were to embark for Cuba.

Shafter, under intense pressure from Washington to depart for Santiago, did not have the transports necessary to move his entire force. He therefore ordered Wood to dismount his cavalry and to select eight out of his 12 companies for the invasion. Roosevelt and Brodie were selected to command the two squadrons in Cuba.

On June 14, after even more high command bungling and mismanagement, the 578-man Rough Rider contingent finally departed from Tampa Bay aboard the Yucatan. ‘We are just like amateurs at war,’ correspondent Richard Harding Davis noted acidly.

Amateurs or not, they were off to change the course of history. Colonel Wood noted ‘that this is the first great expedition our country has ever sent overseas and marks the commencement of a new era in our relations with the world.’ For the men, however, there was little thought of world politics, just much card playing and even an occasional chorus of the Rough Rider’s adopted theme song — ‘There’ll Be a Hot Time in the Old Town Tonight.’

Roosevelt, who often shared the ship’s railing with Buckey O’Neill, was surprised to find that the two-gun Arizona lawman was also ‘a visionary, an articulate emotionalist.’ Under the starlit sky they contemplated the odds against them, with O’Neill expressing a soaring ambition tempered by a dark fatalism. ‘He had taken so many chances when death lay on the hazard,’ T.R. noted, ‘that he felt the odds now were against him.’ Some years before O’Neill had written a short story containing an eerily prescient passage: ‘Death was the black horse that came some day into every man’s camp, and no matter when that day came a brave man should be booted and spurred and ready to ride him out.’

The soldiers reached their destination near Santiago, Cuba, in five days and General Shafter, after conferring with Admiral William Sampson and Cuban rebel leader Calixto Garcia, decided to land his troops at Daiquir and then march inland to Siboney and finally Santiago. Daiquir was supposedly undefended, with a broad beach and even an old wooden pier built by an American iron company years before. On June 22 the troops began to land. They were fortunate to face no opposition, yet the landing was a fiasco. Since there was no transport for the horses and mules, they were lowered by sling into the water and released, or simply pushed off the ships into the sea to swim ashore. Mercifully, by afternoon the Rough Riders were all ashore, although the landings continued into the night.

Shafter promptly ordered General Lawton to occupy Siboney with his infantry division and Wheeler’s dismounted cavalry. Just after dusk on June 23, Wood and Roosevelt entered Siboney. They found Joe Wheeler, ‘a regular gamecock’ as T.R. characterized him, anxious to conduct an armed reconnaissance toward Santiago in hopes of finding the Spanish rearguard. Cuban rebels had spotted enemy troops entrenched a few miles to the north at Las Guasims.

Wheeler moved out at dawn on the 24th with more than 900 men, including all eight Rough Rider companies and 400 men from the regular First and Tenth regiments. The Cubans estimated the Spanish force ahead at 600, but it proved to be three times that number. Moving across unfamiliar terrain against a force of unknown size was dangerous work for seasoned regulars, much less untested volunteers. Wheeler led his regulars down the main road while the Rough Riders traversed a narrow trail to the left. The heat was oppressive in the thick and tangled jungle.

Some three miles from Siboney, a group of Rough Riders led by Captain Allyn Capron and Sergeant Hamilton Fish made contact with the still unseen enemy. As the bullets of the Spaniards’ Mauser rifles whined about them, Capron’s men fanned out, briskly returning fire with their .30 caliber Krag-Jorgensen carbines. Wood and Roosevelt had wisely procured these guns for the unit as replacements for the older, black powder Springfield rifles other volunteers had received. Now the Rough Rider commanders hurried their men forward, deploying them on both sides of the trail.

Cherokee Rough Rider Tom Isbell drew first blood for the Americans, dropping a Spanish sniper just as he received the first of seven wounds — which he somehow survived. Sergeant Fish and Private Ed Culver were also hit at almost the same time. Fish asked Culver, ‘You all right?’ then slumped over, dead. Captain Capron rushed forward to Fish’s body, killing two Spaniards as he advanced before being mortally wounded himself.

Wood calmly led his men forward, taking cover and firing and then advancing again. The Spanish, still well hidden in the jungle, began to melt away before the pressure. Caught up in the excitement of the moment, newspaper correspondent Edward Marshall joined in the combat. The deadly humming of the 7mm Mauser slugs filled the air, like ‘a nasty, malicious little noise,’ wrote Marshall. Within moments he was wounded by a bullet near his spine. Adjutant Tom Hall, witnessing this from afar, mistook Marshall for Wood, and fled to the rear where he reported the colonel dead and the Rough Riders routed. He was later allowed to quietly resign.

Major Brodie was hit in the arm and went down. Six-foot-six Color Sergeant Albert Wright was grazed three times. Captain James McClintock took a bullet in the leg and also fell. Still the Rough Riders advanced, with Roosevelt taking command of Brodie’s squadron as well as his own. O’Neill’s volunteers now joined up with a unit of regulars, and the Spanish began to pull back. With a whoop Captain Robert Huston’s troops opened fire on a group of panic-stricken, fleeing Spaniards. ‘Don’t shoot at retreating men,’ Wood angrily shouted. He ordered the men forward to occupy a deserted, ramshackle building. Black troopers of the Ninth Cavalry now moved up to reinforce the Rough Riders, but the battle was over.

Roosevelt walked the corpse-littered field with Buckey O’Neill. The Rough Riders had lost eight killed and 31 wounded. ‘Colonel,’ O’Neill asked, ‘isn’t it Whitman who said of the vultures that `they pluck the eyes of princes and tear the flesh of kings?’ ‘ Roosevelt, still a bit stunned by the scene, could not recall but later remembered it to be Ezekial: ‘Ye shall eat the flesh of the mighty and drink the blood of the princes of the earth.’

Generals Shafter and Lawton were angry with Wheeler for bringing on an engagement — or walking into an ambush, as many of the regular officers thought. Ambush or not, the Rough Riders had fought their way through, driving a superior force of entrenched infantry from a vital strategic point on the road to Santiago. For six days Shafter kept his men encamped along that road while more supplies and troops came ashore and the road up from the beach was improved.

Already men were dropping in great numbers with fevers, General Wheeler among them. Brigadier General Samuel Sumner took temporary command of the cavalry, with Wood taking over the second brigade. Roosevelt now became colonel of the Rough Riders. Shafter, himself ill, needed to act quickly before sickness further reduced his army. From El Pozo, a commanding hill about five miles east of Santiago, Shafter could easily see the Spanish entrenchments on the San Juan Heights, about a mile and a half away and rising some 125 feet above the valley. A blockhouse stood on the highest of these crests — San Juan Hill — while to its right lay another hill topped with ranch buildings and several old sugar cane cauldrons. It was promptly dubbed Kettle Hill. Between the two heights was a small valley and a pond. Roughly four miles to the north was the Spanish strongpoint of El Caney. Between El Pozo and the San Juan Heights flowed the San Juan River.

Shafter decided to attack on July 1. General Lawton’s Second Infantry Division would assault El Caney. Following Lawton’s success, a force of roughly 8,000 men was to charge the San Juan Heights. Shafter had apparently learned little since the Civil War, when it took a good soldier at least 20 seconds to load and fire his single-shot rifled musket. The entrenched Spaniards could fire eight shots from their 7mm Mausers in the same amount of time. If Major General Arsenio Linares y Pombo’s units had any automatic weapons, the American frontal assault would turn into a bloodbath.

Roosevelt, whose contempt for Shafter was growing by the minute, was astonished at the vagueness of the general’s orders. ‘No reconnaissance had been made,’ he grumbled, ‘and the exact position and strength of the Spaniards were not known.’ Astride his horse, Little Texas, Roosevelt led the Rough Riders forward late on the afternoon of June 30 onto the increasingly congested trail leading to El Pozo. The heat, as always, was intense so he had cast off his jacket in favor of a dark blue shirt, khaki pants, and a polka-dot bandanna around his neck. A similar bandanna floated from his crumpled campaign hat much like a knight’s plume. He carried a pistol retrieved from the Maine on his hip. Four hours later he halted to encamp for the long, sleepless night before the battle.

At 8 a.m. on Friday, July 1, 1898, Captain George Grimes’ battery opened fire on the San Juan Heights. For nearly an hour he dueled with the Spanish artillery. Enemy fire killed one Rough Rider, wounded four others, and brought down Wood’s horse. Shrapnel grazed Roosevelt’s wrist. Shafter finally ordered the cavalry to ford the San Juan River, moving to the right in hopes of meeting up with Lawton. Lawton, however, was having a hard time of it at El Caney, where 500 tenacious Spaniards were putting up a brave defense. Roosevelt got his men across the river and within an hour had them positioned along a sunken trail to the left of Kettle Hill. Spanish sniper fire was as intense as the suffocating heat, however, and the men were quickly pinned down. Volleys now came at regular intervals from the Spanish entrenchments just a few hundred yards away.

Quickly recognizing his position as untenable, Roosevelt turned to his orderly, Harvard man William Saunders, only to find him stretched in the grass, near death from heat prostration. He called to another private, ordering him back up the trail to ask the first general officer he found for permission to charge. As the trooper saluted, a bullet struck his throat and he fell dead into Roosevelt’s arms.

Not far away Buckey O’Neill was strolling along the line smoking a cigarette, ignoring the hail of bullets. His prone men kept begging him to get down, but he laughingly refused, declaring at one point that ‘the Spanish bullet isn’t made that will kill me.’ Moments later a bullet drove through his mouth and out the back of his head. Roosevelt was devastated, believing O’Neill’s death to be the ‘most serious loss that I or the regiment could have suffered.’

An officer suddenly galloped up, breathlessly ordering Roosevelt to support the regulars in their assault on the hills. Instantly mounting Little Texas, Roosevelt galloped up and down shouting orders to his officers and cheering on the men. They needed no encouragement. William Pollock, a Pawnee artist from Guthrie, gave out a chilling war whoop and soon all the men were shouting and rushing forward.

As they advanced into the tall grass, the adrenaline-charged troops came upon the position of the Ninth Cavalry. Captain Henry Barber was holding his men in position, for he had no orders to advance. ‘Then let my men through, sir!’ demanded Roosevelt. He led them on, and the black troopers of the Ninth now joined the charge, orders or not. Two Ninth cavalrymen tore down a wire fence in their path, and Roosevelt galloped forward, waving his hat and yelling ‘Charge!’

The whole line surged forward, as the men of the regular cavalry regiments — the First, Third, Sixth, and Tenth — rushed Kettle Hill alongside the Ninth Cavalry and the Rough Riders. Lieutenant John J. Pershing of the Tenth — whose service with black troops earned him the nickname ‘Blackjack’ — remembered that charge as a moment of unification: ‘White regiments, black regiments, Regulars and Rough Riders, representing the young manhood of the North and South, fought shoulder to shoulder, unmindful of race or color . . . mindful only of their common duty as Americans.’

Atop El Pozo an assortment of officers, foreign observers, and journalists watched in amazement. The foreigners were as one in condemning the folly of the charge. ‘It is gallant, but very foolish,’ said one officer. Melancholy New York World reporter Stephen Crane was lost in the glory of it all. ‘Yes, they were going up the hill, up the hill,’ Crane wrote. ‘It was the best moment of anybody’s life.’

It was certainly the best moment of Colonel Theodore Roosevelt’s life. He was the only man on horseback, but his life seemed charmed. ‘No one who saw Roosevelt take that ride expected him to finish it alive,’ wrote correspondent Richard Harding Davis. ‘He wore on his sombrero a blue polka-dot handkerchief, la Havelock, which, as he advanced, floated out straight behind his head, like a guidon.’ Like Crane, Davis was overcome by the sheer emotion of the charge. ‘Roosevelt, mounted high on horseback, and charging the rifle-pits at a gallop and quite alone, made you feel that you would like to cheer,’ he declared.

Forty yards from the summit, a wire fence stopped Little Texas. Roosevelt dismounted and with his new orderly, Arizona miner Henry Bardshar, jumped the fence and blazed away at the Spanish troops above them. Bardshar killed two Spaniards directly in front of them. Other Rough Riders crowded forward, firing their Krags and taking cover behind the huge sugar cauldrons near the summit. New Mexico troopers planted their guidons on the summit as the defenders fled.

From Kettle Hill Roosevelt could see General Jacob Kent’s First Infantry Division moving painfully up San Juan Hill. At the same time the Rough Riders came under both artillery and volley fire. Suddenly, they heard a drumming sound and a cry went up that the Spaniards had machine guns. Roosevelt, however, recognized the sound. ‘It’s the Gatlings, men, our Gatlings!’ he exclaimed. The troops cheered as Lieutenant John Parker’s battery of rapid-fire Gatling guns raked the Spanish trenches on San Juan Hill.

With the enemy pinned down, now was the time to act. Roosevelt impetuously rushed forward, leaping a wire fence and heading toward San Juan Hill to support the infantry. Suddenly he realized that he had only five men with him, and within moments two of them were hit. Leaving his surviving comrades behind, he angrily backtracked to the crest of Kettle Hill. ‘We didn’t hear you!’ the Rough Riders exclaimed sheepishly. ‘We didn’t see you go. Lead on. We’ll follow.’ And off they went.

They rapidly crossed the little valley, splashing through the pond and up the hill toward the Spanish trenches. Roosevelt and Bardshar were in the lead when two Spaniards jumped up and fired directly at them. Roosevelt returned the fire, killing one of them. The enemy was now in full retreat as Roosevelt’s men overran the trenches and pushed over the crest of San Juan Hill. Suddenly they found themselves overlooking the city of Santiago. As Roosevelt and his exhausted men stood there a staff officer came up, ordering a halt. The men were to entrench and hold the ridge at all costs. Roosevelt found he had but 339 men still fit for service.

Shafter, far to the rear, was characteristically unsure of the outcome. He had lost more than 220 men killed and 1,000 wounded since daybreak and now actually contemplated retreating from the exposed San Juan Heights. Little did he realize how fortunate he had been that General Linares had committed but 1,200 men to defend the Spanish positions. Roosevelt was simply disgusted with his commander. ‘Not since the campaign of Crassus against the Parthians has there been so criminally incompetent a general as Shafter,’ he wrote to his friend Lodge. ‘The battle simply fought itself.’

Two days after the battle, Admiral Cervera’s small squadron challenged the American fleet under Commodore Schley and Admiral William T. Sampson and was promptly wiped out. Santiago then surrendered to General Shafter on July 17. On August 12 the humiliated Spaniards agreed to an armistice that secured the freedom of Cuba and transferred Puerto Rico, Guam, and the Philippines to the United States. The Spanish-American War was over.

Soon after the battle of July 1, Theodore Roosevelt posed with his Rough Riders atop the crest of San Juan Hill. Volunteers and regulars — Hispanic Americans, Native Americans, African Americans, and Anglo Americans — stared grimly yet proudly at the camera. They did not yet know it, but on that bloody hillside they had not only helped liberate Cuba, they had moved to heal their own country’s sectional wounds and made their nation into a world power. Roosevelt had led them, as he soon would the whole nation, into the new century. San Juan Hill was a moment of momentous transition — for the world would never be the same again.


This article was written by Paul Andrew Hutton and originally published in American History Magazine. For more great articles, subscribe to American History magazine today!