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.

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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!

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