THEODORE ROOSEVELT HAD BEEN A NEW YORK STATE assemblyman before turning cowboy; when the disaster of 1886–1887 drove him back to politics, he ran for mayor of New York City. He didn’t win, but he gained enough positive exposure that when a post came open on the city’s police board, he got the job. He tilted against criminals and corrupt policemen in a way that made headlines but little headway, and meanwhile moonlighted as a cheerleader for the Republican party. He stumped on behalf of William McKinley in 1896 and called William Jennings Bryan every kind of dangerous radical. When McKinley won, Roosevelt lined up for a job in the new administration.
The one he landed was assistant secretary of the navy. It was the closest he could get to war during peacetime, and war was his heart’s desire. Roosevelt’s struggle to shake his early weakness would culminate, he dreamed, in the ultimate test of manhood: war. If he could show his courage under fire, he would finally have become a man.
As it happened, there was a war looming. A nationalist revolt in Cuba, one of the last Spanish colonies in the Americas, had triggered repression against the rebels and sympathy among Americans for the rebel cause. Roosevelt wasted little sympathy on the rebels, but he did want a chance to fight Spain. He urged war upon McKinley at all opportunities, which weren’t many, given that he was a mere assistant navy secretary. McKinley rebuffed Roosevelt’s advances.
But Roosevelt had a friend, Leonard Wood, an army surgeon with experience in the West, and also the president’s doctor. Wood agreed with Roosevelt on the need for American action against Spain, and he saw McKinley almost daily. In time the machinations of Roosevelt and Wood became a joke with McKinley. “Have you and Theodore declared war yet?” McKinley typically asked Wood, while the latter was taking his pulse. “No, Mr. President, but we think that you should,” Wood replied.
The pressure mounted on McKinley, from many besides Roosevelt and Wood. New York newspapers, locked in a circulation battle and reckoning that war would boost sales, shamelessly agitated for American belligerence. Eventually McKinley sent a battleship, the Maine, to Havana to register American concern. The ship mysteriously blew up, allowing Roosevelt and the war hawks to blame the Spanish. The pressure on McKinley increased, and finally he succumbed. The president asked Congress for a declaration of war, and Congress obliged.
The legislature thereupon authorized the creation of volunteer regiments, including three of cavalry. Leonard Wood was given command of the 1st Cavalry Regiment, with Roosevelt as his lieutenant colonel. At the suggestion of Roosevelt and Wood, the regiment would be drawn primarily from the Western territories. Word went out, and the one thousand positions were quickly oversubscribed.
Roosevelt was thrilled. He was tickled to be lieutenant to Wood, whose career under arms had included much more than doctoring. “He had served in General Miles’s inconceivably harassing campaigns against the Apaches,” Roosevelt observed, “where he had displayed such courage that he won that most coveted of distinctions—the Medal of Honor; such extraordinary physical strength and endurance that he grew to be recognized as one of the two or three white men who could stand fatigue and hardship as well as an Apache; and such judgment toward the close of the campaigns he was given, though a surgeon, the actual command of more than one expedition against the bands of renegade Indians.”
The enlisted men of the regiment were hardly less impressive to Roosevelt. “They came from the four territories which yet remained within the boundaries of the United States”—New Mexico, Arizona, Oklahoma and Indian Territory—“that is, from the lands that have been most recently won over to white civilization, and in which the conditions of life are nearest those that obtained on the frontier when there still was a frontier.” The recruits possessed traits Roosevelt had long envied. “They were a splendid set of men, these Southwesterners—tall and sinewy, with resolute, weather-beaten faces, and eyes that looked a man straight in the face without flinching,” he said. “In all the world there could be no better material for soldiers than that afforded by these grim hunters of the mountains, these wild rough riders of the plains. They were accustomed to handling wild and savage horses; they were accustomed to following the chase with the rifle, both for sport and as a means of livelihood.”
A few hailed from frontier towns. “But most were from the wilderness, having left their lonely hunters’ cabins and shifting cow-camps to seek new and stirring adventures beyond the sea.” Some of the noncommissioned officers of the regiment were military veterans of the Indian wars. Other had worn badges. “They were sheriffs, marshals, deputy-sheriffs, and deputy-marshals—men who had fought Indians, and still more often had waged relentless war upon the bands of white desperadoes.” Bucky O’Neill was “a famous sheriff throughout the West for his feats of victorious warfare against the Apache, no less than against the white road-agents and man-killers.” A regimental captain from New Mexico had been in numerous scrapes. “He had been shot four times in pitched fights with red marauders and white outlaws.” Several had been marshals and deputies in the Indian Territory. “In the Indian Territory, service as a deputy-marshal meant capacity to fight stand-up battles with the gangs of outlaws.”
The ages of the troopers varied. “The men in the ranks were mostly young, yet some were past their first youth,” Roosevelt said. “These had taken part in the killing of the great buffalo herds, and had fought Indians when the tribes were still on the warpath. The younger ones, too, had led rough lives; and the lines in their faces told of many a hardship endured, and many a danger silently faced with grim, unconscious philosophy.” Some had been to the East, and a few even across the ocean. “Others had been born and bred in the West, and had never seen a larger town than Santa Fe or a bigger body of water than the Pecos in flood.” Several followed the Western habit of adopting nicknames: Cherokee Bill, Happy Jack, Smoky Moore, Rattlesnake Pete.
The regiment included four clergymen. A much larger number still needed saving. “Some were professional gamblers,” Roosevelt wrote. “Some were men whose lives in the past had not been free from the taint of those fierce kinds of crime into which the lawless spirits who dwell on the borderland between civilization and savagery so readily drift.”
The regiment included Texas Rangers. “Of course, these rangers needed no teaching,” Roosevelt said. “They were already trained to obey and to take responsibility. They were splendid shots, horsemen and trailers. They were accustomed to living in the open, to enduring great fatigue and hardship, and to encountering all kinds of danger.”
Benjamin Franklin Daniels had been marshal of Dodge City after that town supplanted Abilene as the destination of choice for Texas cattle drives and became a byword for frontier hijinks. “In the course of his rather lurid functions as a peace officer, he had lost half of one ear—‘bitten off,’ it was explained to me,” Roosevelt said. “Naturally, he viewed the dangers of battle with philosophic calm.”
A bronco-buster from Oklahoma named McGinty shared the cowboy’s distaste for doing anything afoot. He never walked a hundred yards if he could possibly ride. “When McGinty was reproved for his absolute inability to keep step on the drill-ground, he responded that he was pretty sure he could keep step on horseback,” Roosevelt recounted.
The most striking members of the regiment were the Indians. Primarily from the Indian Territory, they were Cherokees, Chickasaws, Choctaws, Creeks and a handful of others. “Only a few were of pure blood,” Roosevelt observed. “The others shaded off until they were absolutely indistinguishable from their white comrades—with whom, it may be mentioned, they all lived on terms of complete equality.” One of the full-blooded Indians was a Pawnee named Pollock—“one of the gamest and best soldiers in the regiment.” Roosevelt reflected on Pollock and on American relations with the Indians in remarking, “He had been educated, like most of the other Indians, at one of those admirable Indian schools which have added so much to the total of the small credit account with which the White race balances the very unpleasant debit account of its dealings with the Red.” Pollock was taciturn, but he had a good hand for writing, and when not fighting, he served as the regimental clerk. Roosevelt discovered, at the front in Cuba, that he possessed a wry sense of humor. “As he was sitting in the Adjutant’s tent working over the returns, there turned up a trooper from the First”—Regiment—“who had been acting as barber. Eyeing him with immovable face, Pollock asked, in a guttural voice, ‘Do you cut hair?’ The man answered, ‘Yes’; and Pollock continued, ‘Then you’d better cut mine,’ muttering, in an explanatory soliloquy, ‘Don’t want to wear my hair like a wild Indian when I’m in civilized warfare.’”
Another impressive Indian was a Cherokee named Holderman. “He was an excellent soldier,” Roosevelt said. “He was a half-breed, and came of soldier stock on both sides and through both races. He explained to me once why he had come to the war: that it was because his people had always fought when there was a war, and he could not feel happy to stay at home when the flag was going into battle.”
The Indians were the best riders in a regiment of first-rate horsemen. Roosevelt recalled the finest of the bunch. “He was mounted on an exceedingly bad bronco, which would bolt out of the ranks at drill. He broke it of this habit by the simple expedient of giving it two tremendous twists, first to one side and then to the other, as it bolted, with the result that, invariably, at the second bound its legs crossed and over it went with a smash, the rider taking the somersault with unmoved equanimity.”
ROOSEVELT’S ROAD TO CUBA RAN THROUGH SAN ANTONIO, where his regiment gathered and trained. His admiration for the volunteers, and his lack of military experience, caused him to blur the line between officers and men. One successful drill session inspired him to give a congratulatory order: “The men can go in and drink all the beer they want, which I will pay for!” The men cheered their lieutenant colonel and all headed for the saloon. Roosevelt was delighted with himself until Leonard Wood pointed out that drinking with the enlisted men was not conducive to military discipline. Roosevelt reddened under the reprimand before blurting out, “Sir, I consider myself the damnedest ass within ten miles of this camp! Good night, sir!”
Roosevelt soon got his role straight, but the men never lost their rambunctiousness. When their training was completed and the regiment prepared to leave for Tampa and then Cuba, San Antonio threw a celebration. The gala concluded with a concert ending in martial tunes, which the conductor bolstered by the firing of cannons. Members of the regiment had been drinking at the celebration, and their discernment was impaired. A few of them mistook the musical cannons for enemy fire upon the conductor and orchestra. “Help him out, boys!” one shouted, pulling his pistols and leaping onto the stage. Others joined him and began blazing away. The flabbergasted audience dove to the ground. The confusion intensified when the bullets shot out the lights, and darkness enveloped the scene. But the unseen enemy failed to return the troopers’ fire, and things settled down. The conductor, a German immigrant, remarked the next day, “I was in the Franco-Prussian War and saw some hot times, but I was about as uneasy last night as I ever was in battle.”
From San Antonio the regiment traveled by train to Tampa. Already the eyes of America were on them. The pens of journalists scribbled profiles of the “Rough Riders,” as headline writers dubbed them. Never had such a picturesque unit entered battle under the American flag. Cowboys and Indians in the same unit, fighting together? The very notion tantalized, even as it assuaged the guilt Americans felt at their country’s mistreatment of the Indians. The Indians in the regiment, apparently, weren’t holding a grudge, for they had volunteered to fight on behalf of the government that had seized their lands and waged war on them.
Roosevelt ensured ample coverage of the Rough Riders. He had learned the art of public relations on the police board in New York, where he had invited reporters to join him on midnight prowls through the tenderloin districts. He continued to cultivate the newsmen, who found him good for a quote or a tidbit about the regiment. Lest they miss something of interest, Roosevelt contracted to write a series of articles for Scribner’s magazine about the Rough Riders and their exploits.
THE FIGHTING UNFOLDED DIFFERENTLY THAN ROOSEVELT expected. At Tampa, army transports were too few for all the regiments and all their gear. Roosevelt, desperate not to be deprived of his testing under fire, jawboned the regiment’s way onto one of the transports, but the horses of all save the officers had to be left behind. The result was a cavalry regiment that went to war on foot. The Rough Riders became rough walkers. McGinty and the other cowboys suffered, but soldiered on.
The regiment performed gallantly in its two engagements with the enemy. “Yesterday we struck the Spaniards and had a brisk fight for 2½ hours before we drove them out of their position,” Roosevelt reported after the first. “We lost a dozen men killed or mortally wounded, and sixty severely or slightly wounded. One man was killed as he stood beside a tree with me. Another bullet went through a tree behind which I stood and filled my eyes with bark.” Roosevelt led the men in a series of charges. “The last charge I led on the left using a rifle I took from a wounded man,” he said. “The fire was very hot at one or two points where the men around me went down like ninepins.”
The second engagement was the crucial one. The San Juan Heights guarded the port of Santiago, and the Americans sought to drive out the Spanish fleet anchored there. The Rough Riders were assigned the task of taking Kettle Hill, part of the heights. Richard Harding Davis, a journalist who became a Roosevelt friend and enthusiast, described the lieutenant colonel as he led the assault on the Spanish lines. “Roosevelt, mounted high on horseback, charging the rifle-pits at a gallop and quite alone, made you feel that you would like to cheer,” Davis wrote. “He wore on his sombrero a blue polka-dot handkerchief, à la Havelock”—a British hero of the Afghan War—“which, as he advanced, floated out straight behind his head like a guidon.”
The Spanish fire, directed down from the heights, was intense and lethal. “The Mauser bullets drove in sheets through the trees and the tall jungle grass, making a peculiar whirring or rustling sound,” Roosevelt recalled. “Some of the bullets seemed to pop in the air, so that we thought they were explosive; and, indeed, many of those which were coated with brass did explode, in the sense that the brass coat was ripped off, making a thin plate of hard metal with a jagged edge, which inflicted a ghastly wound.”
The wounds were many. The Americans carried the day at San Juan, but more than a thousand—from all the regiments—were killed or wounded. Yet Roosevelt couldn’t have been happier. He had been in the thickest of the fighting and hadn’t flinched. Men had been killed to his left and right, and he hadn’t slowed his forward pace. His men had followed him without question. “The man in command must take all the risks which he asks his men to take if he is going to get the best work out of them,” he explained knowingly to a friend back home. “On the day of the big fight I had to ask my men to do a deed that European military writers consider utterly impossible of performance, that is, to attack over open ground unshaken infantry armed with the best modern repeating rifles behind a formidable system of entrenchments. The only way to get them to do it in the way it had to be done was to lead them myself.”
Roosevelt would never forget the thrill of the battle or lose the glow of the victory. Decades later he declared, “San Juan was the great day of my life.”